(-)-(1'R,2'S,5'R)-menthyl (1S,2S,3R,4R)- and (1R,2R,3S,4S)-2-endo-cyano-3-endo-phenylbicyclo<2.2.1>hept-5-ene-2-exo-carboxylate | 142635-85-6

• 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: (-)-(1'R,2'S,5'R)-menthyl (1S,2S,3R,4R)- and (1R,2R,3S,4S)-2-endo-cyano-3-endo-phenylbicyclo<2.2.1>hept-5-ene-2-exo-carboxylate
• 英文别名: (-)-(1'R,2'S,5'R)-menthyl (1S,2S,3R,4R)- and (1R,2R,3S,4S)-2-endo-cyano-3-endo-phenylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylate
• CAS: 142635-85-6；142697-97-0；142697-98-1；142697-99-2
• 化学式: C₂₅H₃₁NO₂
• 分子量: 377.527
• InChiKey: YCTFKJHGFQVHIR-FQTHYSOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  L-薄荷醇 、 (+/-)-2-endo-cyano-3-endo-phenylbicyclo<2.2.1>hept-5-ene-2-exo-carboxylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(-)-(1'R,2'S,5'R)-menthyl (1S,2S,3R,4R)- and (1R,2R,3S,4S)-2-endo-cyano-3-endo-phenylbicyclo<2.2.1>hept-5-ene-2-exo-carboxylate
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with cyclopentadiene

  摘要：

  Several chiral derivatives of (E)-2-cyanocinnamic acid are used as trisubstituted dienophiles, and their asymmetric Diels-Alder reactions with cyclopentadiene are studied. The reactions of (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone with cyclopentadiene, catalyzed by TiCl4, allow the synthesis of enantiomerically pure cycloadducts whose absolute configurations are assigned by an X-ray diffraction study of enantiomerically pure (1S,2S,3R,4R,5R,6R)-iodolactone. The results obtained show that the alpha-cyano group influences asymmetric induction, probably through an influence on the s-cis/s-trans equilibrium of the enoate moiety of the chiral dienophile.

  DOI：

  10.1021/jo00043a025