105192-33-4Relevant academic research and scientific papers
Regioselective Preparation of Fullerene Bis-adducts from Cleavable Macrocyclic Bis-malonates
Trinh, Thi Minh Nguyet,Schillinger, Franck,Guerra, Sebastiano,Meichsner, Eric,Nierengarten, Iwona,Hahn, Uwe,Holler, Michel,Nierengarten, Jean-Fran?ois
, p. 3770 - 3786 (2021)
A series of macrocyclic bis-malonates incorporating either di-tert-butylsilylene or tetra-iso-propyldisiloxane subunits have been prepared and used for the regioselective bis-functionalization of [60]fullerene by double Bingel cyclopropanations. By system
Chemoselective Oxidation of p-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst
Hamada, Shohei,Sugimoto, Koichi,Elboray, Elghareeb E.,Kawabata, Takeo,Furuta, Takumi
supporting information, p. 5486 - 5490 (2020/07/24)
The oxidation of p-methoxy benzyl (PMB) ethers was achieved using nitroxyl radical catalyst 1, which contains electron-withdrawing ester groups adjacent to the nitroxyl group. The oxidative deprotection of the PMB moieties on the hydroxy groups was observed upon treatment of 1 with 1 equiv of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess of PIFA.
Stereocontrolled Total Synthesis of Nonenolide
Sudina, Purushotham Reddy,Motati, Damoder Reddy,Seema, Aravind
, p. 1399 - 1404 (2018/06/29)
Nonenolide (1) was first isolated from the entomopathogenic fungus Cordyceps militaries BCC2816 and exhibited good antimalarial activity against Plasmodium falciparum K1. Structurally, it features a decanolide with a trans-double bond attached to two chir
Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell
Green, Robert A.,Jolley, Katherine E.,Al-Hadedi, Azzam A. M.,Pletcher, Derek,Harrowven, David C.,De Frutos, Oscar,Mateos, Carlos,Klauber, David J.,Rincón, Juan A.,Brown, Richard C. D.
supporting information, p. 2050 - 2053 (2017/04/27)
Electrochemical deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.
Fluorinated Musk Fragrances: The CF2Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone
Callejo, Ricardo,Corr, Michael J.,Yang, Mingyan,Wang, Mingan,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
, p. 8137 - 8151 (2016/06/13)
The difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X-ray studies indeed show that the CF2groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co-workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF2groups, lose their musk fragrance and become less pleasant.
Fluorine in fragrances: Exploring the difluoromethylene (CF2) group as a conformational constraint in macrocyclic musk lactones
Corr, Michael J.,Cormanich, Rodrigo A.,Von Hahmann, Cortney N.,Bühl, Michael,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information, p. 211 - 219 (2015/12/30)
The CF2 group is incorporated into specific positions within the lactone ring of the natural musk lactone, (12R)-(+)-12-methyl-13-tridecanolide, a constituent of Angelica root oil, Angelica archangelica L. The approach is taken as it was antici
Stereoselective total synthesis of stagonolide E
Rajaram, Singanaboina,Ramulu, Udugu,Aravind, Seema,Babu, Katragadda Suresh
, p. 650 - 656 (2015/06/02)
Abstract An efficient and highly stereoselective synthesis of stagonolide E (1) starting from the readily available hexane-1,6-diol (8) was accomplished, employing MacMillan α-hydroxylation, Horner-Wadsworth-Emmons olefination, (Z)-selective Still-Gennari
METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
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Paragraph 0066; 0067; 0068, (2014/11/13)
As shown by the following formula (1), after methyl laurate (2 mmol) and water (8 mL) are added to an ammonium pyrosulfate catalyst (5 mol%), a hydrolysis reaction of methyl laurate is carried out by heating for 24 hours at 60°C while stirring is performed, so that lauric acid can be obtained with a yield of 86%.
N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters
Koshikari, Yoshiki,Sakakura, Akira,Ishihara, Kazuaki
experimental part, p. 3194 - 3197 (2012/07/31)
Reverse micelle-type N,N-diarylammonium pyrosulfate (3-5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.
Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers
Sui, Bin,Yeh, Edmund A.-H.,Curran, Dennis P.
supporting information; experimental part, p. 2942 - 2954 (2010/07/17)
Two different mixture synthesis routes have been used to make the four stereoisomers of petrocortyne A. A first quick and dirty route provided a mixture of the four isomers in nonselective fashion. Mosher and 2-naphthylmethoxyacetic acid (NMA) ester methods were developed to identify the components, and the mixture was partially resolved on analytical chiral HPLC to give the two pure enantiomers of petrocortyne A and the racemate of its diastereomer. A second fluorous mixture synthesis produced all four isomers of petrocortyne A in individual pure form. Comparison of spectra of Mosher derivatives of the synthetic isomers with two supposedly different natural products showed that both natural samples were instead identical and had the (3S,14S) configuration. Likewise, petrocortynes B, D, and F-H are (3S,14S) and petrocortyne D is (3R,14S). Having access to all possible candidate isomers of both petrocortyne A and its Mosher derivatives provided a secure structure assignment not so much because one of the isomers matched the natural product, but because all of the other isomers did not.
