(-)-(2S,3R)-1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-yl)-ethanone | 59056-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2S,3R)-1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-yl)-ethanone
• 英文别名: iso-Georgywood；1-[(2S,3R)-2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone
• CAS: 59056-93-8
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: FVUGZKDGWGKCFE-BZNIZROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  georgywood 反应 48.0h， 以12%的产率得到(-)-(2S,3R)-1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-2-yl)-ethanone
  参考文献：
  名称：

  Cyclization of 1,5-Dienes:  An Efficient Synthesis of β-Georgywood

  摘要：

  In the acid-promoted 1,5-diene cyclization of pseudo- to beta-Georgywood, the cyclization product is obtained with high selectivity in spite of an unfavorable substituent at the C(2)-position of the diene precursor. Preisomerization of the cyclohexene double bond, which occurs in the presence of Bronsted acids, is suppressed with > 1 equiv of MXn-type Lewis acids, whereas RAlX2-type Lewis acids such as > 2 equiv of MeAlCl2 have the additional benefit of steering the double bond of the cyclized product into the desired beta-position. Mechanistic studies revealed a crucial participation or nonparticipation of the carbonyl group in the cyclization reaction, depending on the acid family employed, and allowed finally the development of a cyclization reaction catalyzed by MeAlCl2 that can be generated in situ from precatalyst AlMe3.(1).

  DOI：

  10.1021/jo061668k

文献信息

• A Review of U.S. Patents in the Field of Organic Process Development Published During August and September 2009
  作者：Keith Turner

  DOI：10.1021/op1000429

  日期：2010.3.19

  This article has not yet been cited by other publications.

  本文尚未被其他出版物引用。
• Synthesis and olfactory properties of (−)-(1R,2S)-Georgywood
  作者：Georg Fráter、Urs Müller、Fridtjof Schröder

  DOI：10.1016/j.tetasy.2004.11.003

  日期：2004.12

  The enantiomers of Georgywood(R) were synthesized from (E)-2-methyl-6-methylene-nona-2,7-diene and methacrylaldehyde followed by oxidation of the Diels-Alder adduct and classical racemate separation of the acid with optically-active N-methylephedrine. Conversion to the final ketone and olfactory evaluation showed that the (-)-(1R,2S)-enantiomer is more powerful by a factor of >100 than its antipode. The absolute configuration was determined by conformational studies and CD-analysis. (C) 2004 Elsevier Ltd. All rights reserved.
• Cyclisation Process
  申请人：Schroder Fridtjof

  公开号：US20080114189A1

  公开（公告）日：2008-05-15

  A process of preparation of cis-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1,2,8,8-tetramethylnaphthalene (“β-Georgywood”) from cis-1-[1,2-dimethyl-4(4-methyl-pent-3-enyl)-cyclohex-3-enyl]-ethanone (“Ψ-Georgywood”), comprising the reaction of Ψ-Georgywood with more than one molar equivalent of a Lewis acid. The method allows the preparation of isomeric mixtures that contain a much higher proportion of the olfactorily-desirable β-Georgywood than was previously possible.
• US5707961A
  申请人：——

  公开号：US5707961A

  公开（公告）日：1998-01-13
• US7569732B2
  申请人：——

  公开号：US7569732B2

  公开（公告）日：2009-08-04