52378-69-5

Usage

Uses

Used in Fragrance and Flavor Industry:
DIETHYL TRANS-CINNAMYLPHOSPHONATE 98 is used as a synthetic aroma chemical for imparting a sweet, balsamic, and powdery scent reminiscent of cinnamon and honey. It is widely utilized in the production of perfumes, personal care products, and scented household items.
Used in Food Industry:
In the food industry, DIETHYL TRANS-CINNAMYLPHOSPHONATE 98 is used as a flavoring agent for baked goods, confectionery, and beverages, enhancing their taste and aroma with its unique cinnamon and honey-like scent.

InChI:InChI=1/C13H19O3P/c1-3-15-17(14,16-4-2)12-8-11-13-9-6-5-7-10-13/h5-11H,3-4,12H2,1-2H3/b11-8+

Upstream product

• 7318-33-4 cinnamaldehyde tosylhydrazone 
• 762-04-9 phosphonic acid diethyl ester 
• 104-55-2 3-phenyl-propenal 
• 591-50-4 iodobenzene 
• 1067-87-4 Diethyl allylphosphonate 
• 21040-45-9 Cinnamyl acetate 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 122-78-1 phenylacetaldehyde 
• 183204-00-4 [(diethyloxyphosphinyl)methylidene]triphenylphosphorane 
• 185301-51-3 diethyl 1-benzoyloxy-3-phenyl-2(E)-propenylphosphonate 
• 100-42-5 styrene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 122-52-1 triethyl phosphite 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 52221-91-7 diethyl 3-phenylpropyl-1-phosphonate 

Relevant academic research and scientific papers

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.

Facile access to functionalized chiral secondary benzylic boronic esters: Via catalytic asymmetric hydroboration

Allylic and homoallylic phosphonates bearing an aryl or heteroaryl substituent at the γ- or δ-position undergo rhodium-catalyzed asymmetric hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99:1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asymmetric hydroboration (CAHB) of more highly functionalized internal alkenes. Phosphonate substrates bearing a variety of common heterocyclic ring systems, including furan, indole, pyrrole and thiophene derivatives, as well as those bearing basic nitrogen substituents (e.g., morpholine and pyrazine) are tolerated, although donor substituents positioned in close proximity of the alkene can influence the course of the reaction. Stereoisomeric (E)- and (Z)-substrates afford the same major enantiomer of the borated product. Deuterium-labelling studies reveal that rapid (Z)- to (E)-alkene isomerization accounts for the observed (E/Z)-stereoconvergence during CAHB. The synthetic utility of the chiral boronic ester products is illustrated by stereospecific C-B bond transformations including stereoretentive electrophile promoted 1,2-B-to-C migrations, stereoinvertive SE2 reactions of boron-ate complexes with electrophiles, and stereoretentive palladium- and rhodium-catalyzed cross-coupling protocols.

COMPOUND AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound for improving sensitivity properties and oil crack resistance of an electrophotographic photoreceptor. SOLUTION: The present invention provides a compound represented by formula (1). [R1-R3 independently represent a C1-4 alkyl group, a C1-4 alkoxy group, a C6-14 aryl group or a C7-18 aralkyl group; R4 and R5 independently represent a C1-6 alkyl group, a C6-14 aryl group or H; R6 and R7 independently represent a C1-6 alkyl group or H; a and c independently represent an integer of 0-5; b is an integer of 0-4; r and s independently represent an integer of 0-2; 1≤r+s≤4; t is an integer of 1 or more and 4 or less]. SELECTED DRAWING: Figure 7 COPYRIGHT: (C)2018,JPOandINPIT

Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation

The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.

Synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds

The invention discloses a synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds. According to the synthetic method, alcohols which are cheap, easy to get, wide in source, stable and low in toxicity serve as alkylating reagents, iodine salt which is cheap and easy to get serves as catalysts, no solvent is needed, and the alkyl group phosphorous acid diester compounds can be selectively directly obtained after a reaction. The reaction method is simple, the condition is mild, no organic solvent is needed and operation is simple. According to the method, the requirements for reaction conditions are low, various types of alcohols such as a benzyl group type, an allyl type and a fat type can be utilized as the alkylate reagents to implement the synthesis of different types of substituted alkyl group phosphorous acid diester, and the method can be further expanded to the synthesis of the alkyl group phosphinic acid ester compounds through the reaction between the substituted phosphonous acid diester and the alcohols.

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.

TRIARYLAMINE HYDRAZONE DERIVATIVE AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound that improves the electric characteristics of electrophotographic photoreceptors. SOLUTION: A triarylamine hydrazone compound is represented by formula (1) or a specific structure (R1 and R2 are halogen, an alkyl group, an alkoxy group, or an aryl group). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts

The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.

Palladium-catalyzed allylation/benzylation of H-phosphinate esters with alcohols

The Pd-catalyzed direct alkylation of H-phosphinic acids and hypophosphorous acid with allylic/benzylic alcohols has been described previously. Here, the extension of this methodology to H-phosphinate esters is presented. The new reaction appears general,

TRIARYLAMINE DERIVATIVE AND ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER

A triarylamine derivative is represented by general formula (1) shown below. In general formula (1), R1, R2, and R3 each represent, independently of one another, a halogen atom, an optionally substituted alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 12. In general formula (1), o, p, and q each represent, independently of one another, an integer of at least 0 and no greater than 4, and m and n each represent, independently of one another, an integer of at least 1 and no greater than 2.