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Cas Database

52755-38-1

52755-38-1

Identification

  • Product Name:Benzenemethanol, a-1-propenyl-, (Z)-

  • CAS Number: 52755-38-1

  • EINECS:

  • Molecular Weight:148.205

  • Molecular Formula: C10H12O

  • HS Code:

  • Mol File:52755-38-1.mol

Synonyms:

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Relevant articles and documentsAll total 21 Articles be found

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

Lu, Fu-Dong,Lu, Liang-Qiu,He, Gui-Feng,Bai, Jun-Chuan,Xiao, Wen-Jing

supporting information, p. 4168 - 4173 (2021/04/06)

1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Beltran, Frédéric,Bergamaschi, Enrico,Funes-Ardoiz, Ignacio,Teskey, Christopher J.

, p. 21176 - 21182 (2020/09/17)

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

H-*BEA Zeolite-Catalyzed Nucleophilic Substitution in Allyl Alcohols Using Sulfonamides, Amides, and Anilines

Aoki, Shunsuke,Fujii, Takeshi,Morita, Sachiko,Nishida, Ryo,Ohtsuki, Akimichi,Okumura, Kazu

, (2020/07/24)

Herein, we report a novel zeolite-catalyzed nucleophilic substitution in allyl alcohols. The product yield was improved upon the addition of NaOTf (0.05 mol-percent) using the studied zeolites. The highest yields were observed using H-*BEA(Si/Al2 = 40)/NaOTf. The scope of the reaction with respect to the nucleophile was examined using 1,3-diphenylprop-2-ene-1-ol as a model substrate under optimized reaction conditions. p-Substituted aryl sulfonamides bearing electron-rich or electron-deficient substituents, alkyl sulfonamides, and heteroaryl sulfonamides undergo the amidation reaction to produce their corresponding allyl sulfonamides in good yield. Amides and anilines exhibited low activity under the optimized conditions, however, performing the reaction at 90 °C produced the target product. The scope of the allyl alcohol was investigated using p-toluenesulfonamide as the nucleophile and the reaction proceeded with a variety of allylic alcohols. To probe the practical utility of the H-*BEA-catalyzed amidation reaction, a gram-scale reaction was performed using 1.01 g (4.8 mmol) of allyl alcohol, which afforded the target product in 88 percent yield.

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

Latham, Daniel E.,Polidano, Kurt,Williams, Jonathan M. J.,Morrill, Louis C.

supporting information, p. 7914 - 7918 (2019/10/16)

A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).

Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

Bedná?ová, Eva,Dra?ínsky, Martin,Malatinec, ?tefan,Císa?ová, Ivana,Lamaty, Frédéric,Kotora, Martin

supporting information, p. 2869 - 2878 (2018/08/17)

A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).

Process route upstream and downstream products

Process route

1-phenylbut-3-en-1-one
6249-80-5

1-phenylbut-3-en-1-one

1-Phenyl-3-buten-1-ol
80735-94-0,936-58-3

1-Phenyl-3-buten-1-ol

1-Phenyl-1-butanol
614-14-2

1-Phenyl-1-butanol

Conditions
Conditions Yield
With hydrido(phosphonite)cobalt(I); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In benzene; at 20 ℃; for 16h; Overall yield = 71 percent; Overall yield = 21 mg; Sealed tube; Inert atmosphere; Irradiation; Schlenk technique;
Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 0.33 h / 20 °C / Schlenk technique; Inert atmosphere
1.2: 4 h / 20 °C / Schlenk technique; Inert atmosphere
2.1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; hydrido(phosphonite)cobalt(I) / benzene / 16 h / 20 °C / Sealed tube; Inert atmosphere; Irradiation; Schlenk technique
With aluminum (III) chloride; hydrido(phosphonite)cobalt(I); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In dichloromethane; benzene;
cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

1-phenyl-1-cyclopropylmethanol
1007-03-0

1-phenyl-1-cyclopropylmethanol

Conditions
Conditions Yield
With Schwartz's reagent; sodium hydrogencarbonate; In dichloromethane; Ambient temperature;
75%
11%
With zirconocene hydrochloride; In dichloromethane; at 20 ℃;
75%
11%
Conditions
Conditions Yield
Multistep reaction; (i) tBuLi, THF, ether, pentane, (ii) /BRN= 471223/, (iii) aq. AcOH;
Conditions
Conditions Yield
phenylmagnesium bromide; crotonaldehyde; With chloro-trimethyl-silane; copper(I) thiophene-2-carboxylate; (R)-tol-BINAP; In diethyl ether; at -78 ℃; Inert atmosphere;
With hydrogenchloride; In methanol; diethyl ether; water; optical yield given as %ee; enantiospecific reaction; Inert atmosphere;
phenylmagnesium bromide; With copper(I) thiophene-2-carboxylate; (R)-tol-BINAP; In diethyl ether; at -78 ℃; for 0.25h; Inert atmosphere;
crotonaldehyde; With chloro-trimethyl-silane; In diethyl ether; at -78 ℃; for 8h; enantioselective reaction; Inert atmosphere;
48 % ee
Conditions
Conditions Yield
In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 7.5h;
99.9%
In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 1h; Inert atmosphere;
83%
In tetrahydrofuran; at 0 - 20 ℃;
Conditions
Conditions Yield
bromobenzene; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 1.5h;
crotonaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 2h;
72%
bromobenzene; With magnesium; In tetrahydrofuran;
crotonaldehyde; In tetrahydrofuran; at 0 ℃;
With water; In tetrahydrofuran;
70%
Conditions
Conditions Yield
With triethyl borane; triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; at 25 ℃; for 35h;
73%
8%
Conditions
Conditions Yield
With sodium tetrahydroborate; calcium chloride; In methanol; 1a) 30 min, 25 deg C, 1b) 0 deg C, 1 h;
90%
With potassium tert-butylate; In isopropyl alcohol; at 90 ℃; for 0.533333h; Flow reactor; Inert atmosphere;
(Z)-1-propenyl bromide
590-13-6

(Z)-1-propenyl bromide

benzaldehyde
100-52-7

benzaldehyde

(Z)-1-phenyl-but-2-en-1-ol
52755-38-1

(Z)-1-phenyl-but-2-en-1-ol

Conditions
Conditions Yield
(Z)-1-propenyl bromide; With iodine; magnesium; In tetrahydrofuran; at 60 ℃; Schlenk technique; Inert atmosphere;
benzaldehyde; In tetrahydrofuran; at -78 ℃; for 2h; Schlenk technique; Inert atmosphere;
76%

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