14371-10-9

Basic information

• Product Name: trans-Cinnamaldehyde
• Synonyms: CINNAMALDEHYDE, TRANS-;FEMA 2286;LABOTEST-BB LT00939010;AKOS B004060;AKOS BBS-00003207;3-PHENYLPROPENAL;STYRONE;TRANS-3-PHENYL-2-PROPEN-1-AL
• CAS NO: 14371-10-9
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.16
• EINECS: 203-213-9
• Product Categories: A - D;Aldehydes and Ketones;Cinnamomum;Life Sciences Standards;Natural Compounds;Phytopharma Standards;Standards by Plant Genus;Substance Classification;Aldehydes;Alphabetical;Analytical Standards;Analytical/Chromatography;Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Chromatography;Organic Building Blocks
• Mol File: 14371-10-9.mol
• Article Data: 552

Chemical Properties

• Melting Point: −9-−4 °C(lit.)
• Boiling Point: 250-252 °C(lit.)
• Flash Point: 160 °F
• Appearance: Clear yellow/Liquid
• Density: 1.05 g/mL at 25 °C(lit.)
• Vapor Density: 4.6 (vs air)
• Vapor Pressure: 0.0265mmHg at 25°C
• Refractive Index: n20/D 1.622(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• Water Solubility: 1.1 g/L (20 ºC)
• Sensitive: Air Sensitive
• Stability: Hygroscopic
• Merck: 14,2297
• BRN: 1071571
• CAS DataBase Reference: trans-Cinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Cinnamaldehyde(14371-10-9)
• EPA Substance Registry System: trans-Cinnamaldehyde(14371-10-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-21
• Safety Statements: 26-36/37-37/39-24
• WGK Germany: 3
• RTECS: GD6476000
• F: 10-23
• Hazardous Substances Data: 14371-10-9(Hazardous Substances Data)

Usage

Overview

Cinnamaldehyde, an old flavourant derived from Cinnamon trees and other species of the genus Cinnamomum[1], has now attracted rising interests for its ability of preventing the development of diabetes and its complications[2,3]. As a yellow and viscous liquid, cinnamaldehyde constitutes 98% of essential oil of Cinnamon bark, and was first isolated by Dumas and Péligot[4] and then synthesized in the laboratory by the Italian chemist, Luigi Chiozza (1828-1889) in 1854[5]. In 2007, Subash et al. firstly reported a hypoglycemic and hypolipidemic effect of cinnamaldehyde on streptozotocin (STZ)-induced male diabetic Wistar rats[6]. Cinnamaldehyde has been since extensively studied in animal models of diabetes and obesity. Cassia or Chinese cinnamon is a widely used spice extracted from the inner bark of the cinnamon tree. Cassia has been used for thousands of years for medicinal purposes and is considered to be one of the 50 fundamental herbs in traditional Chinese medicine. Several parts of the Cassia plant are used for medicinal purposes, including the root, bark, leaves, and flowers. Cinnamon extracts have been reported to have various beneficial effects, including antiallergenic, antimicrobial, antiviral, antioxidative, gastroprotective, antiangiogenic, and anti-Alzheimer effects, as well as insulin-like biological activities [7-12]. Cinnamon extracts contain several active compounds, including essential oils (cinnamaldehyde and cinnamyl aldehyde), tannins, mucus, and carbohydrates[13]. Interestingly, cinnamaldehyde, also known as cinnamic aldehyde, shows anti-obesity effects by reducing lipid accumulation and downregulating the peroxisome proliferator-activated receptor-γ, CCAAT/enhancer-binding protein α, and sterol regulatory element-binding protein 1. Furthermore, cinnamaldehyde inhibits lipopolysaccharideinduced microglial activation by targeting the low-density lipoprotein receptor-related protein-1[14]. It was also reported that cinnamaldehyde has antimutagenic effects in cancer cells[15]. Figure 1 the chemical structure of Cinnamaldehyde;

Pharmacokinetics

Cinnamaldehyde naturally exists in trans-cinnamaldehyde form[16]. In an experiment performed by Zhao et al. evaluates the pharmacokinetics of cinnamaldehyde in rats using relative sensitive approach of gas chromatography–mass spectrometry (GC-MS) via oral (500 mg/kg) and intravenous injection (i.v.,20 mg/kg) administration[17]. The results reveals that AUC0-t of cinnamaldehyde via oral administration and via i.v. administration are 1984 ± 531 and 355 ± 53 ng h/ml, respectively. The T1/2 and Tmax of cinnamaldehyde are longer for oral administration (6.7 ± 1.5 h and 1.6 ± 0.5 h) than for i.v. administration (1.7 ± 0.3 h and 0.033 h). The Cmax is 249±36 ng/ml for oral administration, and 547±142 ng/ml for i.v. administration, respectively. The results indicate that the bioavailability of cinnamaldehyde is better improved by i.v. administration than by oral administration. Further, the authors demonstrate that Cmax and AUC0–t are proportional to the dose (from 125 to 500 mg), whereas Tmax and mean residence time does not change in response to dose escalation[17]. Given that cinnamaldehyde and cinnamyl alcohol could transform into each another in rats[17], the authors also analyzes pharmacokinetic property of cinnamyl alcohol in rats plasma. The pharmacokinetic data of cinnamyl alcohol are 1105±337 ng?h/ml for AUC0–t, 6.7±2.8 h for T1/2, 1.5±0.7 h for Tmax, and 221±66 ng/ml for Cmax, at oral dosage of 500 mg/kg. Interestingly, methyl cinnamate has also been discovered in the metabolites. For pharmacokinetic property of methyl cinnamate, interested readers are encouraged to consult Zhao et al. article[17]. In short, cinnamaldehyde is well distributed throughout the body after absorption. Cinnamaldehyde has an option to transform into cinnamyl alcohol and also can be oxidized to cinnamic acid after entering the body. In order to fully understand pharmacokinetic properties of cinnamaldehyde, methyl cinnamate and cinnamyl alcohol should also be determined in the plasma. However, the instability of cinnamaldehyde calls into question that the bioactivity of cinnamaldehyde is likely due to the sum of its metabolites. Therefore, further attempts are expected to address the potential concerns. In addition, the newly developed SME-cinnamaldehyde with improved bioavailability also needs further investigation of anti-diabetic effect.

Applications

Cinnamon extracts have various beneficial effects including antiallergenic, antimicrobial, antiviral, antioxidative, gastroprotective, antiangiogenic and anti-Alzheimer effects as well as insulin-like biological activities. Cinnamaldehyde shows anti-obesity effects by reducing lipid accumulation and downregulating the peroxisome proliferator-activated receptor-γ, CCAAT/enhancer-binding protein α, and sterol regulatory element-binding protein 1. Furthermore, cinnamaldehyde inhibits lipopolysaccharideinduced microglial activation by targeting the low-density lipoprotein receptor-related protein-1. It was also reported that cinnamaldehyde has antimutagenic effects in cancer cells[15]. The effect of cinnamaldehyde on the treatment of cancer and diabetes is highlighted below: Anticancer Kwon et al.[18] reported for the first time that cinnamon extracts induce in vitro and in vivo melanoma cell death through the inhibition of NF-κB and AP-1. A subsequent study showed that HCA is the major antitumorigenic compound found in cinnamon extracts, exerting its growth inhibitory effects in 29 types of human cancer cells in vitro and in SW620 human tumor xenografts in vivo[19]. Other research teams have also reported antitumorigenic effects of cinnamon extracts. They inhibit melanoma cancer cells by inducing the expression of pro-angiogenic factors; they also improved the antitumorigenic activities of CD8[+] T cells by increasing their cytolytic activity[20]. Cinnamon extracts also inhibit vascular endothelial growth factor[VEGF], which was discovered by screening compounds for their inhibitory activity against VEGFR2[21]. Most of the antitumorigenic effects of cinnamon extracts can be attributed to cinnamaldehydes, the main component of the essential oil, responsible for the flavor and aroma of the whole cinnamon. It was reported that cinnamaldehydes inhibited cancer cell proliferation by inhibiting cyclin D1 in several types of tumors[22]. Cinnamaldehydes also induce apoptosis by generating reactive oxygen species[ROS] in HL-60 leukemia cells[23] and through activation of pro-apoptotic Bcl-2 family proteins and the MAPK signaling pathway in human hepatoma cells[24]. Furthermore, dimeric cinnamaldehydes derived from HCA showed greater antitumorigenic effects than monomeric cinnamaldehydes by inducing apoptosis and cell cycle arrest[25]. In addition, a number of studies have revealed that the antitumorigenic effects of HCA and its derivatives are mediated through several molecular mechanisms. A recent study showed that polyphenols bearing a cinnamaldehyde scaffold triggered cell cycle arrest at the G2/M phase and apoptotic cell death in cisplatinresistant human ovarian cancer cells[26], suggesting that cinnamaldehyde compounds could be effective in combination chemotherapies for cancer patients. Overall, the molecular mechanisms underlying the anticancer and antimetastatic effects of cinnamaldehydes are diverse, suggesting that cinnamaldehyde is a multitargeting compound. The differential responsiveness of various cancers to different cinnamaldehyde derivatives must be evaluated to allow selection of the most effective compound for each cancer type. Anti-diabetes Emerging studies have been performed over the past decades to evaluate its beneficial role in management of diabetes and its complications. It is demonstrated that oral administration of cinnamaldehyde ranging from 20 mg/kg?body weight[BW] to 40 mg/kg?BW per day for a duration lasting from 21 to 60 days resulted in a significant improvement in the levels of blood glucose and glycosylated hemoglobin[HbA1C] as well as insulin sensitivity in STZ-induced diabetic rats[27, 28]. And 20 mg/kg?BW is assumed to be the effective dose for preventing the development of diabetes in animals. Further, cinnamaldehyde treatment for 4 weeks increases plasma insulin levels and liver glycogen content, as well as decreases triglyceride[TG] and low-density lipoprotein-cholesterol[LDL] levels in STZ and/or HFD insulted male Wistar rats[29,30]. Furthermore, Camacho et al. found that administration with cinnamaldehyde for 5 weeks to HFD fed C57BL/6J mice significantly led to a reduction in body fat mass gain. However, they claimed that cinnamaldehyde treatment did not alter plasma fasting insulin levels and feed consumption[31]. The reason for the inconsistence regarding insulin regulation could be attributed to that genetic backgrounds of C57BL/6J mice are altered in some production facilities[32,33]. The different substrains of mice may exhibit significant differences in phenotypes[34, 35]. In addition, cinnamaldehyde may exhibit glucose-lowering effect through improving insulin sensitivity in the periphery in Camacho’s study[31]. Cinnamaldehyde has the capacity of improving diabetic adipose tissues by reducing visceral fat deposition, and promoting lipolysis and fatty acid oxidation and thermogenesis, which is associated with an upregulation of energy expenditure genes[UCP1, FOXP2, BPMP4 and PRDM16], an inhibition of PPARγ/CEBP-α and SREBP1, an upregulation of HSL and PNPLA2 and MGL, an induction of AMPK phosphorylation, and an increase in Cpt1a in WAT and Acsl4 in BAT, as well as a stimulation of the sympathetic nervous system. In addition, cinnamaldehyde prevents inflammatory genes expression, and improves GLUTs expression in diabetic animals. Cinnamaldehyde may protect against diabetes by improving insulin sensitivity and glucose uptake through regulating PI3K/IRS-1 and RBP4-GLUT4 pathway in skeletal muscle tissue[37, 38], as well as regulating mitochondria metabolism through PGC-1α/MEF2/GLUT4 pathway in C2C12 cells[36]. Cinnamaldehyde also has positive effects on diabetic liver through improving glycogen syntheses by regulating activities of PK and PEPCK and decreasing RBP4 level as well as normalizing the aberrant liver enzymes, suggesting a beneficial role of this compound in glucose metabolism and insulin sensitivity in diabetic liver[39-41]. Anti-microbial effects Study has confirmed the antimicrobial activity of cinnamaldehyde, cloves, thyme, and rosemary against E. coli O157:H7 and Salmonella[42-44]. Wendakoon and Sakaguchi[1995][45] reported that the carbonyl group of cinnamaldehyde binds to the proteins, preventing amino acid decarboxylase activity in Enterobacter aerogenes. Smid et al.[1996][46] observed the damage to cytoplasmic membrane of Saccharomyces cerevisiae when treated with cinnamaldehyde, leading to excessive leakage of metabolites and enzymes from the cell, and finally loss of viability. Most studies have suggested that the modes of action of essential oils depend on the type of microorganisms, mainly on their cell wall structure and to their outer membrane arrangement. They observed damages due to the significant differences in the outer membranes of gram-negative and gram-positive bacteria[42, 43].

Toxicity

Even now, cinnamaldehyde is still assumed to be a safe natural ingredient agent and well tolerated in human and animals[47]. The concept is also well accepted by FDA and the council of Europe with suggestion of the acceptable daily intake of 1.25 mg/kg. Acute toxicity Cinnamaldehyde is reported to have the high margin of safety, and administered 20 times of effective dose(20 mg/kg)?of this compound did not cause abnormal behavioral signs and disturbed serum chemistry values throughout the study[48]. The acute toxicity of cinnamaldehyde is low, with oral median lethal dose(LD50)?values ranging from a low of 0.6 g/kg BW to a high of 3.4 g/kg BW in different species[49]. Long-term toxicity The results of a three-month study[50] show that body weights are reduced in female rats exposed to 16,500 or 33,000 ppm and in female mice exposed to 8200 ppm or greater. In addition, feed consumption is reduced in all exposed groups of rats and in the highest dose group of mice. Further, exposure to cinnamaldehyde[8200 ppm or greater in rats and 33,000 ppm in female mice] increases the incidence of squamous epithelial hyperplasia of the forestomach. In addition, mice exposed to cinnamaldehyde[males and females exposed to 16,500 ppm and females exposed to 33,000 ppm] also exhibit increased incidence of olfactory epithelial degeneration of the nasal cavity. All rats survived throughout the three-month study. Other Cinnamaldehyde may also show cytotoxicity effects in F344 rat hepatocytes evidenced by depleting glutathione levels[51], and in HepG2 cells evidenced by increasing micronucleus numbers[52]. Behar et al.[53] studied the potential toxicity of this product in human embryonic and lung cells. The results demonstrate that cinnamaldehyde treatment depolymerizes microtubules in human pulmonary fibroblasts. Cinnamaldehyde also decreases cell proliferation and differentiation by inhibiting cell growth and differentiation, and by altering cell morphology and motility as well as increasing DNA strand breaks and cell death. A study performed by Olsen et al. reveals that cinnamaldehyde causes skin irritant by increasing cold pain threshold and decreasing mechanical pain threshold as well as increasing skin temperature and perfusion in human[54].

References

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Safety assessment of food flavor -cinnamaldehyde. Biosafety 2014;3 Hooth MJ, Sills RC, Burka LT, Haseman JK, Witt KL, Orzech DP, Fuciarelli AF, Graves SW, Johnson JD, Bucher JR. Toxicology and carcinogenesis studies of microencapsulated trans-cinnamaldehyde in rats and mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 2004;42:1757-1768. Swales NJ, Caldwell J. Studies on trans-cinnamaldehyde ii: Mechanisms of cytotoxicity in rat isolated hepatocytes. Toxicology in vitro : an international journal published in association with BIBRA 1996;10:37-42. Sanyal R, Darroudi F, Parzefall W, Nagao M, Knasmuller S. Inhibition of the genotoxic effects of heterocyclic amines in human derived hepatoma cells by dietary bioantimutagens. Mutagenesis 1997;12:297-303. Behar RZ, Luo W, Lin SC, Wang Y, Valle J, Pankow JF, Talbot P. 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Chemical Properties

Different sources of media describe the Chemical Properties of 14371-10-9 differently. You can refer to the following data:
1. trans-Cinnamaldehyde is the main component of cassia oil (about 90%) and Sri Lanka cinnamon bark oil (about 75%). Smaller quantities are found in many other essential oils. In nature, the trans-isomer is predominant. trans-Cinnamaldehyde is a yellowish liquid with a characteristic spicy odor, strongly reminiscent of cinnamon. Being an ??,??-unsaturated aldehyde, it undergoes many reactions, of which hydrogenation to cinnamic alcohol, dihydrocinnamaldehyde, and dihydrocinnamic alcohol is important. Cinnamic acid is formed by autoxidation. On an industrial scale, cinnamaldehyde is prepared almost exclusively by alkaline condensation of benzaldehyde and acetaldehyde. Self-condensation of acetaldehyde can be avoided by using an excess of benzaldehyde and by slowly adding acetaldehyde. Cinnamaldehyde is used in many compositions for creating spicy and oriental notes (e.g., soap perfumes). It is the main component of artificial cinnamon oil. In addition, it is an important intermediate in the synthesis of cinnamic alcohol and dihydrocinnamic alcohol.
2. CLEAR YELLOW LIQUID
3. Combustible, yellowish, oily liquid (thickens on exposure to air). Strong pungent, spicy, cinnamon odor.

Uses

Different sources of media describe the Uses of 14371-10-9 differently. You can refer to the following data:
1. trans-Cinnamaldehyde is used in the flavor and perfume industry. It is also used in medicine. It reacts with glutathione to get an adduct 1'-(glutathion-S-yl)-dihydrocinnamaldehyde. It is used to prepare cinnamylidene-bisacetamide by reacting with acetamide. Further, it inhibits xanthine oxidase.
2. Buildingblock - Cinnamaldehyde is an unsaturated aldehyde so it can easily react to many different compounds to be used in a wide range of fragrance compositions. It is also a building block for several agrochemicals (miticides) or for derivatives like cinnamic alcohol, 3-phenylpropanol, cinnamonitrile, 3-phenylpropionylaldehyde (fragrances and as an alternative to enalapril, lisinopril and ramipril).

Definition

ChEBI: The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.

Synthesis Reference(s)

Chemistry Letters, 12, p. 1207, 1983Journal of the American Chemical Society, 93, p. 2080, 1971 DOI: 10.1021/ja00737a057Tetrahedron Letters, 18, p. 1215, 1977

General Description

Clear yellow liquid with an odor of cinnamon and a sweet taste.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

trans-Cinnamaldehyde is incompatible with strong oxidizing agents and strong bases. trans-Cinnamaldehyde can also react with sodium hydroxide.

Fire Hazard

trans-Cinnamaldehyde is combustible.

InChI:InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4-

Synthetic route

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With 3-methyl-5-deaza-10-oxaflavin; toluene-4-sulfonic acid In 1,4-dioxane for 1h; Product distribution; Heating; other 3-methyl-5-deaza-10-oxaflavins; other alcohols;	100%
With manganese(IV) oxide In hexane for 2h; Ambient temperature;	100%
With molecular sieve; In dichloromethane for 0.5h; Ambient temperature;	100%

5-phenyl-4,5-dihydro-1H-pyrazole (936-47-0) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With benzeneseleninic anhydride In dichloromethane for 4h; Ambient temperature;	100%

(E)-cinnamaldehyde dimethylacetal (4364-06-1) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Ambient temperature;	100%
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 0.5h; Hydrolysis;	100%
With tin(ll) chloride; naphthalene In dichloromethane for 0.0833333h; Ambient temperature;	99%

2,3-dibromo-3-phenyl propanal (66894-04-0, 62248-40-2) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran for 0.5h; Ambient temperature;	100%

2-(trans-styryl)-3-ethyl-1,3-oxazolidine (1021956-61-5) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With diazomethane; copper(II) bis(trifluoromethanesulfonate) In diethyl ether; dichloromethane at 5 - 10℃;	100%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) + benzyl alcohol (100-51-6) → (E)-3-phenylpropenal (14371-10-9) + benzaldehyde (100-52-7)

Conditions	Yield
With potassium carbonate In toluene at 20℃; for 12h;	A 15% B 99%

3-phenyl-propionaldehyde (104-53-0) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 6h; Sealed tube;	98%
With 4-methyl-morpholine; bis(benzonitrile)palladium(II) dichloride; silver trifluoromethanesulfonate In tetrahydrofuran; dichloromethane for 12h; Ambient temperature;	88%
With 4-methyl-morpholine; bis(benzonitrile)palladium(II) dichloride; silver trifluoromethanesulfonate In tetrahydrofuran; dichloromethane for 12h; Product distribution; Ambient temperature; different aldehydes and reagent;	88%

Phenylpropargyl aldehyde (2579-22-8) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → (E)-3-phenylpropenal (14371-10-9) + tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2)

Conditions	Yield
In water Ambient temperature;	A 98% B n/a

trans-cinnamaldehyde diethylacetal (25226-98-6) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With nitric acid; acetic anhydride at -50℃;	98%
With aluminum oxide; Oxone for 0.0266667h; Hydrolysis; Microwave irradiation;	89%
With tin(ll) chloride In dichloromethane for 1h; Ambient temperature;	84%

2-[(E)-2-phenylethenyl]-1,3-dioxolane (83977-12-2, 5660-60-6) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With Ru(CH3CN)3(triphos)(OTf)2 (triphos = CH3C(CH2PPh2)3); acetone for 6h; Ambient temperature;	98%
With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h;	96%
With tin(ll) chloride In dichloromethane for 2h; Ambient temperature; other dioxolanes, other acetals and other pyran;	95%

(E)-1,1-diacetoxy-3-phenylprop-2-ene (64847-78-5) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With Montmorillonite K10 In dichloromethane for 0.75h; Heating;	98%
With aminosulfonic acid In benzene for 0.25h; Heating;	96%
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide); water at 20℃; for 0.0666667h; solid-phase reaction;	96%

1-phenylprop-2-ynyl acetate (16169-88-3, 84681-19-6, 116119-86-9, 116182-55-9) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With water; silver hexafluoroantimonate In tetrahydrofuran at 80℃; for 0.2h; Meyer-Schuster rearrangement; microwave irradiation;	98%
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 60℃; for 1h; Meyer-Schuster Rearrangement; stereoselective reaction;	70%
With methyl trifluoromethanesulfonate In 2,2,2-trifluoroethanol at 70℃; for 1h;	65%

(Z)-cinnamyl alcohol (4510-34-3) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; oxygen; copper(I) bromide In acetonitrile at 20℃; for 16.5h; Schlenk technique;	98%

Sodium; 6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-hexanoate → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;	97.9%

trans-3-phenylprop-2-enyl chloride (21087-29-6) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With N-ethylmorpholine N-oxide In N,N-dimethyl-formamide r.t., 1 h, 50 deg C, 4 h;	97%
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 0.916667h;	84%
With ethanol; hexamethylenetetramine
Multi-step reaction with 3 steps 1.1: sodium iodide / acetone / 1.5 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere; Sealed tube 2.2: 6 h / 40 °C / Inert atmosphere 3.1: 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate / dichloromethane; water / 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium iodide / acetone / 1.5 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere; Sealed tube 2.2: 6 h / 40 °C / Inert atmosphere 3.1: 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate / dichloromethane; water / 45 °C View Scheme

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) + 2-nitro-benzaldehyde (552-89-6) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With hydrogenchloride; aluminum isopropoxide In ethyl acetate; benzene	97%

allylbenzene (300-57-2) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride In 1,2-dichloro-ethane at 50℃; for 2h; stereoselective reaction;	96%
With water; oxygen; palladium diacetate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 24h; Reagent/catalyst; Solvent; Green chemistry; regioselective reaction;	85%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 60℃; for 10h;	76%

2-styryl-1,3-dithiane (69178-10-5) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;	96%
With p-iodoxybenzoic acid In dimethyl sulfoxide at 25℃; for 0.75h;	91%
With Amberlite IR-120; palladium on activated charcoal In methanol for 36h; Heating;	74%
With Dimethoxymethane; oxalic acid In nitromethane at 60℃; for 25h;	67%
With Dess-Martin periodane In dichloromethane; water; acetonitrile at 20℃; for 1h;

3,3-bis(dodecylthio)-1-phenyl-1-propene + Dimethoxymethane (109-87-5) → (E)-3-phenylpropenal (14371-10-9) + 1-dodecylsulfanylmethylsulfanyldodecane (31336-25-1)

Conditions	Yield
With oxalic acid In nitromethane at 60℃; for 14h;	A 95% B 96%

tris(ethoxyvinyl)borane (1151545-40-2) + benzaldehyde (100-52-7) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
Stage #1: tris(ethoxyvinyl)borane With diethylzinc In toluene at -78℃; for 0.333333h; Inert atmosphere; Stage #2: benzaldehyde In toluene at -78 - 20℃; for 14h; Inert atmosphere; Stage #3: With hydrogenchloride; water In diethyl ether; toluene at 0℃; pH=> 4; Inert atmosphere;	96%

1-Phenyl-2-propyn-1-ol (4187-87-5) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With trifluoroacetic acid; [Ru(η3-2-C3H4Me)(CO)(1,1'-(Ph2P)2-ferrocene)][SbF6] In tetrahydrofuran for 3.5h; Meyer-Schuster rearrangement; Heating;	95%
With [Re(κ3-P,N,S-Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO)3]SbF6 at 80℃; for 0.25h; Catalytic behavior; Time; Meyer-Schuster Rearrangement; Inert atmosphere; Schlenk technique;	93%
With [Re(κ3-P,N,S-Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO)3]SbF6 In tetrahydrofuran at 80℃; for 0.0833333h; Meyer-Schuster rearrangement; Microwave irradiation; Inert atmosphere; regioselective reaction;	92%

2-styryl-1,3-dithiane (69178-10-5) → 1.3-propanedithiol (109-80-8) + (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With magnesium(II) perchlorate; water; methylene green In acetonitrile Irradiation;	A n/a B 95%
With magnesium(II) perchlorate; water; methylene green In acetonitrile Mechanism; Irradiation; various dithio derivatives;	A n/a B 95%

1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene (71700-50-0) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With dioxochloro(trimethylsiloxy)chromate(VI) In dichloromethane for 1h;	95%
With quinolinium monofluorochromate(VI) In dichloromethane; N,N-dimethyl-formamide for 15h; Ambient temperature;	66%

(E)-2-(2-phenylethenyl)-1,3-dithiolane (87094-78-8) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;	95%
With cerium(III) chloride; sodium iodide In acetonitrile for 3.5h; Heating;	93%
With iron(III) chloride; potassium iodide In methanol for 3h; Heating;	90%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.25h;	78%
With O-phenyl phosphorodichloridate; N,N-dimethyl-formamide; sodium iodide 1.) acetonitrile, few min, room temp., 2.) 5 h, room temp.; Yield given. Multistep reaction;

2-styryl-1,3-oxathiolane (113124-71-3) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; nitrobenzaldehyde polymer In dichloromethane for 2h; Ambient temperature;	95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; β‐cyclodextrin In water; acetone at 20℃; for 0.333333h;	90%
With 4-nitrobenzaldehdye; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 0.0833333h; Ambient temperature;	75%

C15H14O3S → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With triethylamine In dichloromethane	95%

Phenylpropargyl aldehyde (2579-22-8) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With Pd3Pb/SiO2; RhSb/SiO2; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr; for 4.3h;	94%
With water; triphenylphosphine; benzoic acid In tetrahydrofuran at 65℃; for 24h; diastereoselective reaction;	87%
With palladium on activated charcoal; ethanol Hydrogenation;
With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water for 1h;
With hydrogen; silica gel In (2)H8-toluene at 100℃; under 3800.26 Torr; for 15h; diastereoselective reaction;	n/a

3-Phenyl-1-propanol (122-97-4) → (E)-3-phenylpropenal (14371-10-9) + 3-phenyl-propionaldehyde (104-53-0)

Conditions	Yield
With p-CO2H-IBX In N,N-dimethyl-formamide at 55 - 60℃; for 4h;	A 5% B 94%

2-styryl-1,3-dithiane-1-oxide (387391-37-9) → (E)-3-phenylpropenal (14371-10-9)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 20℃; for 12h;	94%

(E)-3-phenylpropenal (14371-10-9) + phenylmagnesium bromide → (E)-1,3-diphenyl-2-propen-1-ol (62668-02-4)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 16h;	100%
In diethyl ether at 0 - 20℃; for 8h;	39%
With diethyl ether

(E)-3-phenylpropenal (14371-10-9) → 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;	100%
With baker's yeast; D-glucose; resin XAD 1180 In water at 28℃; for 24h;	100%
With (7,8-benzoquinolinato)hydrido(aqua)bis(triphenylphosphine)iridium(III) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen; N-ethyl-N,N-diisopropylamine In toluene at 80℃; under 760.051 Torr; for 4h;	98%

(E)-3-phenylpropenal (14371-10-9) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid In water; acetonitrile at 20℃; under 760.051 Torr; for 150h; UV-irradiation;	100%
With oxygen; potassium carbonate; 1,3-bis(mesityl)imidazolium chloride In water; N,N-dimethyl-formamide at 25℃; for 16h;	99%
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In toluene at 10℃; for 1h; Product distribution; var. solvents; other reaction partners; other aldehydes;	95%

(E)-3-phenylpropenal (14371-10-9) → (2E)-3-phenyl-2-propen-1-ol (4407-36-7)

Conditions	Yield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;	100%
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 0.4h; Reduction; Heating;	100%
With borohydride Ultra resin In methanol at 20℃; for 4h;	100%

(E)-3-phenylpropenal (14371-10-9) + ethyl acetoacetate (141-97-9) → 2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester (137153-74-3)

Conditions	Yield
In ethanol	100%
With ethanol; sodium ethanolate at -10℃;

(E)-3-phenylpropenal (14371-10-9) + phenylacetylene (536-74-3) → (1E)-1,5-diphenylpent-1-en-4-yn-3-ol (63124-66-3, 128812-14-6)

Conditions	Yield
Stage #1: phenylacetylene With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran at 23 - 25℃; for 3h; Further stages.;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	97%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; pentane at -78℃; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; pentane at -78℃;	89%

(E)-3-phenylpropenal (14371-10-9) + ethyl 2-cyanoacetate (105-56-6) → (2E,4E)-2-cyano-5-phenyl-2,4-pentadienoic acid ethyl ester (41109-95-9)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.25h; Knoevenagel Condensation; Green chemistry;	100%
With zinc(II) chloride at 100℃; for 1.5h;	92%
With 1-methyl-piperazine at 25 - 30℃; for 0.166667h; Knoevenagel condensation;	91%

(E)-3-phenylpropenal (14371-10-9) + 2-Methoxypropene (116-11-0) → [(E)-5-Methoxy-3-(1-methoxy-1-methyl-ethoxy)-hexa-1,5-dienyl]-benzene (148587-30-8)

Conditions	Yield
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; acetic acid In dichloromethane for 18h; Ambient temperature;	100%
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃;	83%
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition;	83%

(E)-3-phenylpropenal (14371-10-9) + trimethylsilyl cyanide (7677-24-9) → (E)-4-phenyl-2-(trimethylsiloxy)but-3-enenitrile (100573-50-0, 40326-21-4, 79248-45-6)

Conditions	Yield
With zinc(II) iodide In dichloromethane at 20℃; for 2h; Addition;	100%
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 19℃; for 36h;	99%
With tin-tungsten mixed oxide, Sn/W molar ratio = 2, calcined at 800 °C In 1,2-dichloro-ethane at 22 - 23℃; for 1h; Inert atmosphere;	99%

(E)-3-phenylpropenal (14371-10-9) + 2-propylidene malonic acid dimethyl ester (18795-82-9) → 2-[(2E,4E)-2-Methyl-5-phenyl-penta-2,4-dien-(E)-ylidene]-malonic acid monomethyl ester (143468-50-2)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In methanol for 24h; Ambient temperature;	100%

(E)-3-phenylpropenal (14371-10-9) + sodium 6-aminohexanoate (7234-49-3) → Sodium; 6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-hexanoate

Conditions	Yield
In di-isopropyl ether; water for 0.0416667h; Product distribution; Ambient temperature; separation of aldehyde;	100%

(E)-3-phenylpropenal (14371-10-9) → cinnamic nitrile (1885-38-7)

Conditions	Yield
With trimethylsilylacetylene; zinc(II) chloride In chloroform for 4h; Ambient temperature;	100%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation;	100%
With hydroxylamine hydrochloride In 1-methyl-pyrrolidin-2-one at 100℃; for 0.0833333h;	100%

(E)-3-phenylpropenal (14371-10-9) → cinnamaldehyde oxime (59336-59-3)

Conditions	Yield
With hydroxylamine hydrochloride	100%
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 20℃; for 0.5h;	90%
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 25℃; Inert atmosphere;	85%

(E)-3-phenylpropenal (14371-10-9) + 4-methoxy-aniline (104-94-9) → (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline (88315-63-3)

Conditions	Yield
With magnesium sulfate In dichloromethane for 4h; Ambient temperature;	100%
With magnesium sulfate In ethyl acetate for 1h; Ambient temperature;	100%
In neat (no solvent) for 0.25h;	100%

(E)-3-phenylpropenal (14371-10-9) + 4-methoxy-aniline (104-94-9) → N-cinnamylidene-p-anisidine (80542-40-1)

Conditions	Yield
With magnesium sulfate In ethyl acetate at 20℃; Inert atmosphere;	100%
Ambient temperature;	98%
In toluene for 3.5h; Reflux;	90%

(E)-3-phenylpropenal (14371-10-9) + chloro-trimethyl-silane (75-77-4) + phenyllithium (591-51-5) → (E)-1,3-diphenyl-1-trimethylsilyloxy-2-propene (94740-99-5)

Conditions	Yield
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran Further stages.;	100%
1) THF, -20 deg C, 15 min; 2) THF, RT, 12 h; Yield given. Multistep reaction;

(E)-3-phenylpropenal (14371-10-9) + orthoformic acid triethyl ester (122-51-0) → trans-cinnamaldehyde diethylacetal (25226-98-6)

Conditions	Yield
With lithium tetrafluoroborate In ethanol at 40℃; for 2h;	100%
With N-Bromosuccinimide In ethanol at 20℃; for 0.5h; Inert atmosphere;	97%
aminosulfonic acid at 25℃; for 2h;	92%

(E)-3-phenylpropenal (14371-10-9) + ethyl iodoacetae (623-48-3) → (E)-ethyl 3-hydroxy-5-phenylpent-4-enoate (95728-97-5)

Conditions	Yield
With indium iodide In tetrahydrofuran for 17h; Ambient temperature;	100%
With manganese; copper(l) iodide; trifluoroacetic acid In acetonitrile at 20℃; for 12h; Reformatsky Reaction; Schlenk technique; Inert atmosphere;	93%
With indium In tetrahydrofuran for 1.5h; Ambient temperature;	89%

(E)-3-phenylpropenal (14371-10-9) + benzylamine (100-46-9) → (E,E)-4-aza-1,5-diphenylpenta-1,3-diene (119353-37-6)

Conditions	Yield
With magnesium sulfate In dichloromethane for 0.5h; Heating;	100%
With aluminum oxide for 12h;	100%
In diethyl ether at 25℃;	94%

(E)-3-phenylpropenal (14371-10-9) + benzylamine (100-46-9) → N-((E)-3-phenylallylidene)benzylamine (60293-41-6)

Conditions	Yield
With 4 A molecular sieve In benzene for 2h; Ambient temperature;	100%
In toluene at 23℃; for 36h; Molecular sieve; Inert atmosphere;	85%
With 4 A molecular sieve In dichloromethane at 0℃; for 12h;

(E)-3-phenylpropenal (14371-10-9) + malononitrile (109-77-3) → (E)-2-(3-phenylallylidene)malononitrile (41109-96-0)

Conditions	Yield
With aluminum oxide Inert atmosphere; Neat (no solvent);	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;	100%
With fluorapatite at 20℃; for 1.5h; Knoevenagel condensation;	98%

(E)-3-phenylpropenal (14371-10-9) + Methyltriphenylphosphonium bromide (1779-49-3) → (E)-1-Phenyl-1,3-butadiene (16939-57-4)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;	100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 0.25h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; cyclohexane at 0 - 20℃; for 2h; Wittig olefination;	96%
Stage #1: Methyltriphenylphosphonium bromide In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at 0 - 20℃; for 10h; Inert atmosphere;	96%

(E)-3-phenylpropenal (14371-10-9) + allyltributylstanane (24850-33-7) → (E)-1-phenyl-1,5-hexadien-3-ol (79299-29-9)

Conditions	Yield
With maleic acid at 20℃; for 2h;	100%
(S)-Tol-BINAP*AgNO3 In ethanol; water at -40℃; for 20h; Alkylation;	98%
With tin(ll) chloride In acetonitrile for 1h;	97%

(E)-3-phenylpropenal (14371-10-9) + 5-Trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enylamine (176848-87-6) → [(E)-3-Phenyl-prop-2-en-(E)-ylidene]-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-amine (176848-93-4)

Conditions	Yield
With 4 A molecular sieve In tetrahydrofuran Ambient temperature;	100%

(E)-3-phenylpropenal (14371-10-9) + N,N'-diacetylpiperazin-2,5-dione (3027-05-2) → 1-Acetyl-3-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-piperazine-2,5-dione

Conditions	Yield
With potassium In toluene for 0.0333333h; Irradiation;	100%

(E)-3-phenylpropenal (14371-10-9) + hexa-2,4-dienyl bromide (63072-78-6) → (1E,5E)-1-Phenyl-4-vinyl-hepta-1,5-dien-3-ol

Conditions	Yield
With indium In N,N-dimethyl-formamide at 0℃; for 3h;	100%

Upstream product

• 108-31-6 maleic anhydride 
• 953-21-9 N-phenylcinnamaldimine 
• 100-42-5 styrene 
• 14189-82-3 3-(N-Methylanilino)-2-propenal 
• 102-69-2 tri-n-propylamine 
• 64-17-5 ethanol 
• 61912-03-6 2-hydroxy-4-phenyl-3-butenenitrile 
• 2579-22-8 Phenylpropargyl aldehyde 
• 4360-47-8 cinnamonitrile 
• 1885-38-7 cinnamic nitrile 
• 3056-73-3 cinnamanilide 
• 102-92-1 cinnamoyl chloride 
• 109-63-7 trifluoroborane diethyl ether 
• 100-52-7 benzaldehyde 

Downstream Products

• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 1466-20-2 2-[(E,E)-4-phenylbuta-1,3-dienyl]pyridine 
• 76606-12-7 α-(3-phenyl-2-propenylidene)-γ-butyrolactone 
• 2637-05-0 2-methyl-6-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)pyridine 
• 7073-51-0 3.3-bis-acetylamino-1t-phenyl-propene-⁽¹⁾ 
• 64299-64-5 2-benzyl-5-phenyl-penta-2,4-dienal 
• 134415-29-5 5-oxo-3,4,5-triphenyl-valeraldehyde 
• 5438-08-4 4-trans-cinnamylidene-2-phenyl-4H-oxazol-5-one 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 104-54-1 3-Phenylpropenol 
• 3152-68-9 1-phenyl-pent-1-en-3-one 
• 109801-00-5 (1E)-1-phenylhept-1-en-3-ol 
• 17942-89-1 triethyl-(3-phenyl-propenyloxy)-silane 
• 6413-49-6 4,4,6-trimethyl-2-trans-styryl-[1,3]dioxane 

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Complementary relationship between trans-Cinnamaldehyde (cas 14371-10-9) and trans-cinnamyl acetate and their seasonal variations in Cinnamomum osmophloeum ct. cinnamaldehyde08/05/2019

Cinnamomum osmophloeum ct. cinnamaldehyde is endemic to Taiwan. It has many bioactivities and is suitable for replacing commercial cinnamons (C. zeylanicum and C. cassia) due to the high content of trans-cinnamaldehyde (CAl) with extremely low content of coumarin. To expand its application, the ...detailed

Relevant articles and documents

Phenylpropanoid glycosides from Conyza japonica

Three new phenylpropanoid glycosides, named 1-O-[3-O-acetyl-α-L- rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]-3-hydroxycinnamaldehyde (1), 1-O-[2,3-O-diacetyl-α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranosyl]-3-methoxycinnamaldehyde (2), and 1-O-[3-O-acetyl-α-L

Efficient preparation of trans-α,β-unsaturated aldehydes from saturated aldehydes by oxidative enamine catalysis

A mild and highly efficient amine-catalyzed, IBX-mediated oxidation of aldehydes to (E) selective α,β-unsaturated aldehydes has been achieved in good yields. The process features a new oxidation of enamines to iminium ions in a catalytic fashion.

Switching the Z / e selectivity in the palladium(II)-catalyzed decarboxylative heck arylations of trans -cinnamaldehydes by solvent

The Z/E selectivity of Pd(II)-catalyzed decarboxylative Heck-type arylations of trans-cinnamaldehydes can be controlled readily by switching the reaction solvent. Depending on the type of solvent used, each of the two isomeric products can be obtained with good to excellent Z/E ratio. In THF, Z-isomers were formed preferentially, whereas DMF provided the E-isomers predominantly.

Unravelling Some of the Key Transformations in the Hydrothermal Liquefaction of Lignin

Using both experimental and computational methods, focusing on intermediates and model compounds, some of the main features of the reaction mechanisms that operate during the hydrothermal processing of lignin were elucidated. Key reaction pathways and their connection to different structural features of lignin were proposed. Under neutral conditions, subcritical water was demonstrated to act as a bifunctional acid/base catalyst for the dissection of lignin structures. In a complex web of mutually dependent interactions, guaiacyl units within lignin were shown to significantly affect overall lignin reactivity.

Selective oxidation of alcohols with a new reagent: Iron(III) nitrate supported on aluminum silicate

A selective and effective oxidation of alcohols, except aliphatic alcohols, such as 1-hexanol or 1-octyl alcohol, to the corresponding aldehydes and ketones using a new reagent, iron(III) nitrate supported on aluminum silicate, under heterogeneous conditions with reflux with 85-98% yield is described. Copyright Taylor & Francis Group, LLC.

The application of N,N′-dibromo-N,N′ -1,2-ethanediylbis-(p-toluenesulphonamide) as a powerful reagent for the oxidation of primary and secondary alcohols to aldehydes and ketones

Aliphatic and benzylic alcohols are readily oxidized to aldehydes and ketones in good yields under mild conditions by N,N′-dibromo-N,N′ -1,2-ethanediylbis(p-toluenesulphonamide) [BNBTS].

Sequential cross-metathesis/phosphorus-based olefination: stereoselective synthesis of 2,4-dienoates

A variety of stereodefined 2,4-dienoates have been prepared in a stereoselective manner by sequencing olefin cross-metathesis (CM) with phosphorus-based olefination reactions (Wittig and Horner-Wadsworth-Emmons) in good yield using commercially available reagents.

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Microwave-assisted oxidation of alcohols with N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide and poly(N-bromobenzene-1,3-disulfonamide) under solvent-free conditions

An efficient and mild methodology for the oxidation of primary and secondary alcohols to the corresponding carbonyl functions is described with N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and poly(N-bromobenzene-1,3-disulfonamide) using microwave irradiation under solvent-free conditions. Aliphatic, benzylic and allylic alcohols are rapidly oxidized without over-oxidation to carboxylic acids. Secondary carbinols are slowly oxidized so that the reaction is highly chemoselective.

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Allylic amine formation by imination of allylic tellurides

The imination of allylic phenyl tellurides with [N-(p-toluenesulfonyl)imino]phenyliodinane or chloramine-T affords the corresponding allylic amines via [2,3]sigmatropic rearrangement of the tellurimide intermediates in high yields. Application to chiral cinnamyl 2-(1-dimethylaminoethyl)ferrocenyl telluride results in the formation of the corresponding chiral allylic amine, 3-phenyl-3-tosylaminopropene, with 93% ee.

Oxidative deselenylation with sodium perborate and sodium percarbonate

In the presence of acetic anhydride, both sodium perborate and sodium percarbonate have been found to be effective reagents for the oxidation of α-phenylselenocarbonyl compounds to α,β-unsaturated carbonyl compounds.

Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors

The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction

A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.