(1R,6R,8S)-3-ethoxycarbonyl-8,11-dimethyltricyclo<6.3.0.0^2.6>undecane-2,10-dien-4-one | 134053-17-1

• 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: (1R,6R,8S)-3-ethoxycarbonyl-8,11-dimethyltricyclo<6.3.0.0^2.6>undecane-2,10-dien-4-one
• 英文别名: ethyl (3aR,6aR,7aS)-3,7a-dimethyl-5-oxo-3a,6,6a,7-tetrahydro-1H-cyclopenta[a]pentalene-4-carboxylate
• CAS: 134053-17-1
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: PLYAZDMEGCHBIR-JJMVLAAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S*,4S*,5S*)-4-acetoxy-1,6-dimethyl-cis-bicyclo<3.3.0>octa-2,6-diene 在 palladium on activated charcoal lithium hydroxide 、 sodium hydroxide 、 高氯酸 、 PCC-MS₄A 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氢氧化钾 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (1R,6R,8S)-3-ethoxycarbonyl-8,11-dimethyltricyclo<6.3.0.0^2.6>undecane-2,10-dien-4-one
  参考文献：
  名称：

  Asymmetric Heck reaction: a catalytic asymmetric synthesis of the key intermediate for .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.-triol and .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.,14-tetrol

  摘要：

  A catalytic asymmetric synthesis of the key intermediates 21 and 22 for the capnellenols has been achieved (80% ee) by an asymmetric Heck reaction followed by an anion capture process. Furthermore, an improved synthetic route to (+/-)-capnellenols has been also developed.

  DOI：

  10.1021/jo00013a004

文献信息

• Asymmetric heck reaction-anion capture process. A catalytic asymmetric synthesis of the key intermediates for the Capnellenols
  作者：Katsuji Kagechika、Takashi Ohshima、Masakatsu Shibasaki

  DOI：10.1016/s0040-4020(01)80534-2

  日期：1993.2

  A catalytic asymmetric synthesis of the key intermediates 4 and 15 for the capnellenols has been achieved through an asymmetric Heck reaction followed by the acetate anion capture process. Furthermore, the above reaction has been successfully applied to an asymmetric Heck reaction -amine capture process.

  通过不对称的Heck反应和随后的乙酸根阴离子捕获过程，实现了萘酚的关键中间体4和15的催化不对称合成。此外，上述反应已成功地用于不对称的Heck反应-胺捕获过程。
• Asymmetric Heck reaction: a catalytic asymmetric synthesis of the key intermediate for .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.-triol and .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.,14-tetrol
  作者：Katsuji Kagechika、Masakatsu Shibasaki

  DOI：10.1021/jo00013a004

  日期：1991.6

  A catalytic asymmetric synthesis of the key intermediates 21 and 22 for the capnellenols has been achieved (80% ee) by an asymmetric Heck reaction followed by an anion capture process. Furthermore, an improved synthetic route to (+/-)-capnellenols has been also developed.