(+)-(2R,3S)-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: (+)-(2R,3S)-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；Ethanone, 1-((2R,3S)-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-, rel-；1-[(2R,3S)-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-MEDUHNTESA-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：

  (+)-1-[1,2-dimethyl-4-(4-methyl-pent-3-enyl)-cyclohex-3-enyl]-ethanone 在 磷酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以7%的产率得到(+)-(2R,3S)-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：

  Synthesis and olfactory properties of (−)-(1R,2S)-Georgywood

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.11.003

文献信息

• US7449592B2
  申请人：——

  公开号：US7449592B2

  公开（公告）日：2008-11-11
• 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.