ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate | 321156-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate
• 英文别名: (-)-ethyl 4-hydroxy-2,3,3-trimethylcyclopentanecarboxylate；ethyl 4-hydroxy-2,2,3-trimethylcyclopentanecarboxylate；ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane-1-carboxylate
• CAS: 321156-45-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: BPYKVYMOKOWSFV-VGMNWLOBSA-N

物化性质

• 沸点：
  257.9±33.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(+)-(1R,3S)-ethyl 2,3,3-trimethyl-4-oxocyclopentanecarboxylate
  参考文献：
  名称：

  天然（-）-β-necrodol及其对映异构体的酶辅助对映选择性合成。

  摘要：

  DOI：

  10.1021/jo0013812
• 作为产物：
  描述：

  ethyl 2,3,3-trimethyl-4-oxocyclopentanecarboxylate 在 sodium tetrahydroborate 、 乙酸乙烯酯 、 Amano AK lipase 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以450 mg的产率得到ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate
  参考文献：
  名称：

  天然（-）-β-necrodol及其对映异构体的酶辅助对映选择性合成。

  摘要：

  DOI：

  10.1021/jo0013812

文献信息

• First enantioselective total synthesis of both enantiomers of lancifolol. Correlation: absolute configuration/specific rotation
  作者：Jean-Marie Galano、Gérard Audran、Honoré Monti

  DOI：10.1016/s0040-4039(01)01202-3

  日期：2001.8

  The first enantioselective total synthesis of both enantiomers of lancifolol has been accomplished using a Z-stereoselective Peterson olefination and a palladium-catalyzed cross-coupling reaction as key steps. This approach allows us to correlate the relationship between absolute configuration and specific rotation, to date both unknown.

  Lancifolol的两种对映异构体的第一个对映选择性全合成反应都是通过Z-立体选择性彼得森烯化反应和钯催化的交叉偶联反应作为关键步骤完成的。这种方法使我们能够将绝对配置和特定旋转之间的关系关联起来，到目前为止都是未知的。
• Synthesis and Bioassay of Racemic and Chiral <i>trans</i>-α-Necrodyl Isobutyrate, the Sex Pheromone of the Grape Mealybug <i>Pseudococcus maritimus</i>
  作者：Yunfan Zou、Kent M. Daane、Walt J. Bentley、Jocelyn G. Millar

  DOI：10.1021/jf904452v

  日期：2010.4.28

  A concise synthesis of the racemic form of the female-produced pheromone of the grape mealybug was developed. The synthesis was readily adapted to production of both enantiomers of the pheromone via lipase-catalyzed kinetic resolution of an intermediate in the synthesis. Replicated field trials revealed that, contrary to a preliminary report, the (R,R)- rather than the (S,S)-enantiomer is the attractive stereoisomer. Lithium aluminum hydride reduction of the insect-produced compound to a-necrodol followed by analysis on a chiral stationary phase GC column showed that the insect-produced material was actually an 85:15 mixture of the (R,R)- and (S,S)-enantiomers. The racemic form of the pheromone was highly attractive to male mealybugs, and in one of two field bioassays, the racemic material was significantly more attractive than the pure (R,R)-enantiomer, suggesting that the (S,S)-enantiomer might act synergistically.