(1S,5R)-6,6-Dimethyl-4-(((1S,2S,5S)-2,6,6-trimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)methyl)bicyclo[3.1.1]hept-3-en-2-one

被引:1
作者
Ardashov, Oleg V. [1 ,2 ]
Korchagina, Dina V. [1 ]
Bagryanskaya, Irina Yu. [1 ]
Volcho, Konstantin P. [1 ]
Salakhutdinov, Nariman F. [1 ]
机构
[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentiev Ave 9, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Dept Nat Sci, Pirogova Str 1, Novosibirsk 630090, Russia
基金
俄罗斯基础研究基金会;
关键词
verbenone; dimerization; extended enolate; Michael addition; VERBENONE;
D O I
10.3390/M1465
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and convenient procedure for the gamma, beta-dimerization of verbenone was developed. The dimer was obtained during aging with KOH without a solvent. The process proceeds as the formation of the extended enolate of verbenone and its Michael addition to other molecules of verbenone. The product yield was 82% after purification by column chromatography and recrystallization.
引用
收藏
页数:4
相关论文
共 22 条
[1]  
Ali Babar, 2015, Asian Pacific Journal of Tropical Biomedicine, V5, P601, DOI 10.1016/j.apjtb.2015.05.007
[2]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[3]  
[Anonymous], 2008, SADABS, version 2008/1
[4]   Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease [J].
Ardashov, Oleg V. ;
Pavlova, Alla V. ;
Il'ina, Irina V. ;
Morozova, Ekaterina A. ;
Korchagina, Dina V. ;
Karpova, Elena V. ;
Volcho, Konstantin P. ;
Tolstikova, Tat'yana G. ;
Salakhutdinov, Nariman F. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (11) :3866-3874
[5]   DIENEDIOLATES FROM UNSATURATED CARBOXYLIC-ACIDS - MICHAEL ADDITION OF DILITHIUM BUTA-1,3-DIENE-1,1-DIOLATE (FROM CROTONIC ACID) TO UNSATURATED-KETONES [J].
BALLESTER, P ;
COSTA, A ;
RASO, AG ;
GOMEZSOLIVELLAS, A ;
MESTRES, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1711-1717
[6]  
Bessiere-Chretien Y., 1971, B SOC CHIM FR II-CH, V6, P2189
[7]   BARK BEETLE PHEROMONES: PRODUCTION OF VERBENONE BY A MYCANGIAL FUNGUS OF Dendroctonus frontalis [J].
Brand, J. M. ;
Bracke, J. W. ;
Britton, L. N. ;
Markovetz, A. J. ;
Barras, S. J. .
JOURNAL OF CHEMICAL ECOLOGY, 1976, 2 (02) :195-199
[8]   Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects [J].
Ju, Chung ;
Song, Sumi ;
Hwang, Sunyoung ;
Kim, Chorong ;
Kim, Minkyoung ;
Gu, Jail ;
Oh, Yu-Kyoung ;
Lee, Kyeong ;
Kwon, Jinsun ;
Lee, Kiho ;
Kim, Won-Ki ;
Choi, Yongseok .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (19) :5421-5425
[9]   THE USE OF 4,4-DISUBSTITUTED NOPINONES FOR NATURAL-PRODUCT SYNTHESIS - SYNTHESIS OF ELEMANOID SESQUITERPENES [J].
KATO, M ;
WATANABE, M ;
VOGLER, B ;
AWEN, BZ ;
MASUDA, Y ;
TOOYAMA, Y ;
YOSHIKOSHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7071-7076
[10]  
Lindgren BS, 2002, ENVIRON ENTOMOL, V31, P759, DOI 10.1603/0046-225X-31.5.759