(E,1R,5S)-3-(4-methoxybenzylidene)-6,6-dimethylbicyclo[3.1.1]heptan-2-one | 118712-13-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,1R,5S)-3-(4-methoxybenzylidene)-6,6-dimethylbicyclo[3.1.1]heptan-2-one
• CAS: 118712-13-3
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: BHTDYNIOOVWTQR-RKIJOGDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E,1R,5S)-3-(4-methoxybenzylidene)-6,6-dimethylbicyclo[3.1.1]heptan-2-one 在 palladium on activated charcoal 氢气 、 sodium 、 异丙醇 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 18.0h， 生成 (1R,2S,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis and structural determination of new chiral auxiliaries derived from (−)-β-pinene

  摘要：

  New chiral auxiliaries, alcohols syn-11a,e and syn-12a,e, were readily synthesized in a stereoselective manner from (-)-beta-pinene. Their stereochemical determinations have been made on the basis of nOe experiments. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00523-x
• 作为产物：
  描述：

  (1R)-(+)-诺蒎酮 、 4-甲氧基苯甲醛 在 氢氧化钾 作用下， 反应 24.0h， 生成 (E,1R,5S)-3-(4-methoxybenzylidene)-6,6-dimethylbicyclo[3.1.1]heptan-2-one
  参考文献：
  名称：

  Synthesis and structural determination of new chiral auxiliaries derived from (−)-β-pinene

  摘要：

  New chiral auxiliaries, alcohols syn-11a,e and syn-12a,e, were readily synthesized in a stereoselective manner from (-)-beta-pinene. Their stereochemical determinations have been made on the basis of nOe experiments. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00523-x

文献信息

• Configuration assignment of stereogenic centers in a β-pinene derivative by 1H NMR and molecular modeling
  作者：Kátia S.P. Perry、Jorge L.O. Domingos、Ayres G. Dias、Sergio Pinheiro、Antonio J.R. da Silva、Paulo R.R. Costa

  DOI：10.1016/j.molstruc.2005.09.001

  日期：2006.2

  The absolute configuration of three contiguous newly generated stereocenters in (1R,2R,3S,5S,1'R)-3-(1'-(4-methoxyphenyl)ethyl)-6, 6-dimethylbicyclo [3.1.1] heptan-2-ol (6), stereoselectively prepared from beta-pinene in four steps, was established on the basis of H-1 NMR data and molecular modeling. (c) 2005 Elsevier B.V. All rights reserved.