50592-83-1Relevant academic research and scientific papers
Synthesis of Bicyclo[n.1.0]alkanes by a Cobalt-Catalyzed Multiple C(sp3)?H Activation Strategy
Zhang, Zhuo-Zhuo,Han, Ye-Qiang,Zhan, Bei-Bei,Wang, Sai,Shi, Bing-Feng
supporting information, p. 13145 - 13149 (2017/09/28)
A cobalt-catalyzed dual C(sp3)?H activation strategy has been developed and it provides a novel strategy for the synthesis of bicyclo[4.1.0]heptanes and bicyclo[3.1.0]hexanes. A key to the success of this reaction is the conformation-induced methylene C(sp3)?H activation of the resulting cobaltabicyclo[4.n.1] intermediate. In addition, the synthesis of bicyclo[3.1.0]hexane from pivalamide, by a triple C(sp3)?H activation, has also been demonstrated.
Unprecedented copper-mediated oxidative demethylation of propionamides via bidentate-chelation assistance
Liu, Jing-Hui,Cui, Mian,Lu, Xiao-Yu,Zhang, Zhen-Qi,Xiao, Bin,Fu, Yao
supporting information, p. 1242 - 1245 (2016/01/15)
A copper-mediated directed demethylation of propionamides has been developed. This reaction proceeds predominantly at the α-methyl groups of aliphatic amides with high efficiency and provides a unique tool for the direct cleavage of unactivated C(sp3)-C(sp3) bonds. The directing groups can be smoothly removed to afford the corresponding alkyl carboxylic acids.
1-ORTHOFLUOROPHENYL SUBSTITUTED 1, 2 , 5-THIAZOLIDINEDIONE DERIVATIVES AS PTP-AS INHIBITORS
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Page/Page column 86, (2010/11/27)
Compounds of the formula (I) are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. Accordingly, the compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.
Attempts To Trap Radicals Formed in Solution by a Magnesium Surface
Walborsky, H. M.,Topolski, M.,Hamdouchi, C.,Pankowski, J.
, p. 6188 - 6191 (2007/10/02)
The synthesis of 2,2'-azo-2-methyl-6-heptene (1) is discribed.Photolytic decomposition of 1 in ether gave rise to the 1,1-dimethyl-5-hexenyl radical clock (2) which yielded 1,1,2-trimethylcyclopentane (3), 6-methyl-1-heptene (4), and 2-methyl-1,6-heptadiene (5) in the ratio of 1:0.72:0.56, respectively.The ratio did not change appreciably when a well-stirred mixture of 1 and 5 equiv of magnesium powder was photolyzed.Moreover, the solution gave a negative test (2,2'-biquinoline) for the presence of Grignard reagent.Thus, it has been esperimentally demonstrated that the radicals formed in solution do not react with a magnesium surface to form Grignard reagents.
Stereoselective Synthesis of Moenocinol and Assignment of Its Carbon-13 Nuclear Magnetic Resonance Spectrum
Coates, Robert M.,Johnson, Mark W.
, p. 2685 - 2697 (2007/10/02)
A stereoselective synthesis of moenocinol (1), the sesquiterpene alcohol liberated by hydrolysis of the antibiotic moenomycin, is described.Alkylation of isobutyric acid dianion with 5-bromo-1-pentene followed by reduction with lithium aluminum hydride and benzylation provided 1-benzyloxy-2,2-dimethyl-6-heptene (4).Hydrolysis and cleavage of the epoxide of 4 with periodic acid gave 6-benzyloxy-5,5-dimethylhexanal (6). 2-Phenylthio-6-benzyloxy-5,5-dimethylhexanoic acid (8a) was prepared from 6 by chromic acid oxidation and α-phenylsulfenylation.Reaction of the dianion of 8a with geranyl bromide followed by esterification and hydride red uction afforded phenylthio alcohol 10a.Simultaneous reductive elimination and debenzylation of the corresponding acetate (10b) with lithium in ammonia gave (E)-2,2,8,12-tetramethyl-5-methylene-7,11-tridecadien-1-ol (11). (Z)-1-Benzyloxy-6-bromo-3-methyl-4-hexene (17b) was prepared from the benzyl ether of nerol by the following four steps: regioselective ozonolysis, borohydride reduction, formation of the tosylate and displacement with bromide ion.The reaction of the Grignard reagent from 17b with the aldehyde (12) secured by oxidation of 11 afforded an alcohol which was oxidized to (2Z,13E)-1-benzyloxy-3,8,8,14,18-pentamethyl-11-methylene-2,13,17-nonadecatrien-7-one (33).The 6,7-trans (Z) enol phosphate 34, formed by phosphorylation of the enolate anion of 33, underwent reduction with lithium in ammonia to (2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-2,6,13,17-nonadecatetraen-1-ol (1) which was identical with moenocinol obtained from moenomycin.The 6,7-cis isomer (32b) of moenocinol was also prepared by a Wittig reaction between aldehyde 12 and phosphorane 18 and subsequent reductive debenzylation.Carbon-13 NMR spectral data for synthetic and natural moenocinol compared favorably; a consistent set of assignments for the 13C NMR absorptions is deduced from comparisons with model compounds.
