Carbon-Acylation of Benzoic Anhydride Derivatives by Electroreduction

2019 ◽  
Vol 2 (22) ◽  
pp. 29-32
Author(s):  
Masato Matsunami ◽  
Ikuzo Nishiguchi ◽  
Hirofumi Maekawa ◽  
Shun Mizoguchi
Keyword(s):  

1993 ◽  
pp. 857-861 ◽  
Author(s):  
Isao SHIBUYA ◽  
Katsumi YONEMOTO ◽  
Akihiro OISHI ◽  
Masahiko YASUMOTO ◽  
Yoichi TAGUCHI ◽  
...  
Keyword(s):  


1973 ◽  
Vol 51 (12) ◽  
pp. 2024-2032 ◽  
Author(s):  
A. G. Brook ◽  
J. M. Duff

The reactions of a series of silyl-substituted vinylmetallic reagents with acetic and benzoic anhydride have been investigated as a general route to α,β-unsaturated ketones having a silyl group attached to the carbon–carbon double bond. The reaction has been found to be generally applicable for acetyl derivatives provided low temperatures are used but the reaction with benzoic anhydride gives poorer results. The i.r. and u.v. spectra of the ketones are discussed. The characterization of novel 1,4-dienes obtained as by-products in the syntheses is also described.





1962 ◽  
Vol 40 (3) ◽  
pp. 445-448 ◽  
Author(s):  
Denys Cook

The complex of boron trifluoride with benzoic anhydride has been prepared. One molecule of anhydride coordinates three molecules of boron trifluoride. The infrared spectrum shows that coordination takes place at the carbonyl groups, whose frequency is lowered some 200 cm−1. There is no trace of the benzoylium cation, C6H5O+. Although the spectra are complex, tentative assignments are made.



2017 ◽  
Vol 73 (11) ◽  
pp. 1735-1738
Author(s):  
Michael A. Land ◽  
Katherine N. Robertson ◽  
Jason A. C. Clyburne

The title compound, C20H22O3, was formed in the reaction between 2,4,6-trimethylbenzoic acid andN,N-diisopropylethylamine in the presence of 1,3-dichloro-1,3-bis(dimethylamino)propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half molecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-trimethylphenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, molecules are linked by weak C—H...O hydrogen bonds and C—H...π interactions. The packing features wavy chains that extend parallel to [001].



1998 ◽  
Vol 275 (1) ◽  
pp. G138-G150
Author(s):  
Diego Sbrissa ◽  
Amyia Hajra ◽  
Khalil N. Bitar

The source of early production of sn-1,2-diacylglycerol (DAG) has for a long time been exclusively linked to hydrolysis of phosphatidylinositol 4,5-diphosphate, which on receptor activation is hydrolyzed into DAG and inositol 1,4,5-trisphosphate. We have investigated the origin of lipid sources of DAG production in smooth muscle cells, in response to contraction induced by peptide agonists. We have performed a quantitative analysis of the molecular species of DAG formed in relation to the known molecular composition of parent phospholipids. The molecular species of phospholipids are sufficiently unique that the phospholipid origin of DAGs and its quantitative contribution to their formation can be measured by HPLC. Cell suspensions (10–15 × 106 cells/ml) from the circular muscle of rabbit rectosigmoid were incubated in the presence of the contractile peptide agonist bombesin (BB) at 10−6 M. Reactions were stopped at different time intervals from 30 s to 4 min. DAGs were extracted, purified by TLC, and benzoylated with benzoic anhydride. The benzoylated DAGs were first purified by TLC and then by normal phase HPLC before they were injected onto a reverse-phase column and eluted isocratically. Furthermore, phospholipids in the lipid extract [phosphatidylinositol (PI), phosphatidylcholine (PC), phosphatidylserine (PS), and phosphatidylethanolamine (PE)] were purified by TLC and similarly analyzed after hydrolysis to DAGs with phospholipase C (PLC). The DAG molecular species profiles for PI, PC, PS, and PE were all unique. Contraction of cells with BB gave noticeable increases (17–55%) in newly formed DAGs. The major phospholipid source of the newly formed DAGs at 30 s was only ∼30% from PI, and the remainder was from PC. In contrast, after 4 min of BB stimulation, a decrease was seen in newly formed DAGs in the peak specific for PI hydrolysis. The data suggest that BB-induced contraction by activation of PLCs results in hydrolysis of different phospholipids. The DAGs formed as a result are qualitatively and quantitatively distinct. This could be the basis for the kinetically different pattern of sustained contraction observed with BB.



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