(-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate | 321156-42-7

• 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,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate
• 英文别名: 2,2,3-trimethyl-4-methylenecyclopentanecarboxylic acid ethyl ester；ethyl (1R,3R)-2,2,3-trimethyl-4-methylidenecyclopentane-1-carboxylate
• CAS: 321156-42-7
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: NALYLJMPDRPEER-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 lithium 、 乙二胺 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.15h， 生成 (1R,4R)-(3,4,5,5-tetramethyl-2-cyclopentenyl)methyl isobutyrate
  参考文献：
  名称：

  Synthesis and Bioassay of Racemic and Chiral trans-α-Necrodyl Isobutyrate, the Sex Pheromone of the Grape Mealybug Pseudococcus maritimus

  摘要：

  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.

  DOI：

  10.1021/jf904452v
• 作为产物：
  描述：

  ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate 在 草酰氯 、 四氯化钛 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate
  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

• Enzyme-Assisted Enantioselective Synthesis of Natural (−)-β-Necrodol and Its Enantiomer
  作者：Jean-Marie Galano、Gérard Audran、Lionel Mikolajèzyk、Honoré Monti

  DOI：10.1021/jo0013812

  日期：2001.1.1
• 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.