- Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
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Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.
- Martínez, Javier,de la Cruz-Martínez, Felipe,Martínez de Sarasa Buchaca, Marc,Fernández-Baeza, Juan,Sánchez-Barba, Luis F.,North, Michael,Castro-Osma, José A.,Lara-Sánchez, Agustín
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p. 460 - 468
(2021/04/06)
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- Agent having neurotrophic factor-like activity
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The present invention provides a pharmaceutical agent having high safety and a neurotrophic factor-like activity, which contains, as an active ingredient, any one compound included in fatty acids each having 8 carbon atoms (C8) or having 10 carbon atoms (C10) to 12 carbon atoms (C12) or fatty acid esters thereof, such as 3,7-dimethyloctanoic acid ethyl ester, geranicacidethyl ester, and the like, eachof whichhas 8 carbonatoms (C8), decanoic acid methyl ester, trans-2-decenoic acid, trans-2-decenoic acid methyl ester, trans-2-decenoic acid ethyl ester, trans-2-decenoic acid-2-decenyl ester, trans-2-decenoic acid cyclohexyl ester, trans-2-decenoic acid isopropyl ester, trans-3-decenoic acid methyl ester, trans-9-decenoic acid methyl ester, and the like, each of which has 10 carbon atoms (C10), trans-10-undecenoic acid methyl ester, trans-10-undecenoic acid ethyl ester, and the like, each of which has 11 carbon atoms (C11), and dodecanoic acid, and the like, each of which has 12 carbon atoms (C12), or salts thereof or prodrugs thereof.
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Paragraph 0043-0044
(2016/01/25)
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- Enantioselective allylic hydroxylation of w-alkenoic acids and esters by P450 BM3 monooxygenase
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Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.
- Neufeld, Katharina,Henssen, Birgit,Pietruszka, J?rg
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supporting information
p. 13253 - 13257
(2015/02/19)
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- Copper-catalyzed C(sp3)-C(sp3) bond formation using a hypervalent iodine reagent: An efficient allylic trifluoromethylation
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An efficient copper-catalyzed allylic trifluoromethylation reaction has been developed. This reaction provides a general and straightforward way to synthesize allylic trifluoromethylated compounds under mild conditions.
- Wang, Xi,Ye, Yuxuan,Zhang, Songnan,Feng, Jiajie,Xu, Yan,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 16410 - 16413
(2011/11/29)
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- AGENT HAVING NEUROTROPHIC FACTOR-LIKE ACTIVITY
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The present invention provides a pharmaceutical agent having high safety and a neurotrophic factor-like activity, which contains, as an active ingredient, any one compound included in fatty acids each having 8 carbon atoms (C8) or having 10 carbon atoms (C10) to 12 carbon atoms (C12) or fatty acid esters thereof, such as 3,7-dimethyloctanoic acid ethyl ester, geranicacidethyl ester, and the like, eachof whichhas 8 carbonatoms (C8), decanoic acid methyl ester, trans-2-decenoic acid, trans-2-decenoic acid methyl ester, trans-2-decenoic acid ethyl ester, trans-2-decenoic acid-2-decenyl ester, trans-2-decenoic acid cyclohexyl ester, trans-2-decenoic acid isopropyl ester, trans-3-decenoic acid methyl ester, trans-9-decenoic acid methyl ester, and the like, each of which has 10 carbon atoms (C10), trans-10-undecenoic acid methyl ester, trans-10-undecenoic acid ethyl ester, and the like, each of which has 11 carbon atoms (C11), and dodecanoic acid, and the like, each of which has 12 carbon atoms (C12), or salts thereof or prodrugs thereof.
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- A new versatile synthesis of esters from Grignard reagents and chloroformates
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Cross-coupling reactions of chloroformates with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a rapid and straightforward method for the synthesis of esters. Georg Thieme Verlag Stuttgart.
- Bottalico, Daniela,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
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p. 974 - 976
(2008/02/02)
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- Selective esterification of aliphatic carboxylic acids in the presence of aromatic carboxylic acids over monoammonium salt of 12-tungstophosphoric acid
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Monoammonium salt of 12-tungstophosphoric acid [(NH4)H 2PW12O40] was found to be a practical and useful heterogeneous catalyst for an efficient and selective esterification of aliphatic carboxylic acids with alcohols in the presence of aromatic carboxylic acids. The heteropoly acid-based heterogeneous catalyst has the advantages of a simple workup procedure, water insolubility, and good activity. Copyright Taylor & Francis LLC.
- Giri,Prabhavathi Devi,Gangadhar,Narasimha Rao,Lingaiah,Sai Prasad,Prasad
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- A facile, catalytic and environmentally benign method for esterification of carboxylic acids and transesterification of carboxylic esters with nearly equimolar amounts of alcohols
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A practical and green chemical process for the esterification of carboxylic acids with alcohols and transesterification of carboxylic esters in good to excellent yields by using K5CoW12O14· 3H2O (0.1 mol%) as catalyst is reported. The catalyst exhibited remarkable reusable activity. Georg Thieme Verlag Stuttgart.
- Bose, D. Subhas,Satyender, Apuri,Das, A. P. Rudra,Mereyala, Hari Babu
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p. 2392 - 2396
(2008/02/08)
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- Triethylborane-mediated hydrogallation and hydroindation: Novel access to organogalliums and organoindiums
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Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.
- Takami, Kazuaki,Mikami, Satoshi,Yorimitsu, Hideki,Shinokubo, Hiroshi,Oshima, Koichiro
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p. 6627 - 6631
(2007/10/03)
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- LONG CHAIN UNSATURATED OXYGENATED COMPOUNDS AND THEIR USE IN THE THERAPEUTICAL, COSMETIC AND NUTRACEUTICAL FIELD
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Long-chain unsaturated oxygenated compounds and their use in the therapeutical, cosmetic and nutraceutical field. Use of compounds of formula R-X wherein X is a primary alcoholic functional group -CH20H, a carboxylic functional group -COON or a C1-C4 alkyl ester group, and of mono-, di- and tri-glycerides of acid compounds R-COON and of pharmaceutically acceptable salts of those acids, wherein R is a hydrocarbon chain having from 19 to 35 carbon atoms, which is saturated or unsaturated, including from one to five ethylenic or acetylenic unsaturations, linear or branched, including from one to five methyl branches, and optionally substituted by from one to three hydroxyl groups, for the preparation of pharmaceutical or nutraceutical compositions useful for the treatment and prevention of pathologies related to a high concentration of cholesterol and lipids, pathologies associated with an increased ability of the blood platelets to aggregate and with a reduced concentration of oxygen, in the treatment of ageing processes, for the preparation of compositions of nutritional integrators aimed at weight loss and cosmetic compositions useful in the treatment and prevention of skin damage caused by free radicals.
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- A practical transformation of aldehydes into (E)-iodoalkenes with geminal dichromium reagents
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A catalytic cycle of a chromium salt in a stereoselective transformation of aldehydes to (E)-l-iodoalkenes using a geminal dichromium reagent, is assembled with zinc, Me3SiCl, and NaI in dioxane.
- Takai, Kazuhiko,Ichiguchi, Tetsuya,Hikasa, Shintaro
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p. 1268 - 1270
(2007/10/03)
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- Kinetics of epoxidation of alkyl esters of undecylenic acid: Comparison of traditional routes vs. Ishii-Venturello chemistry
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Epoxidation of undecylenic acid and its methyl and ethyl esters with aqueous H2O2 was carried out by using different traditional routes, ion exchange resin, and the newly developed synergistic usage of heteropoly acids and phase transfer catalysis in a biphasic system. The so-called Ishii-Venturello chemistry was employed to develop a kinetic model. Interesting selectivities are obtained.
- Yadav,Satoskar
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p. 397 - 407
(2007/10/03)
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