(-)-(1'S,2'R,4'S)-bornyl (1S,2R,3S,4R)- and (1R,2S,3R,4S)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate | 142635-89-0

• 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'S,2'R,4'S)-bornyl (1S,2R,3S,4R)- and (1R,2S,3R,4S)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate
• 英文别名: (-)-(1'S,2'R,4'S)-bornyl (1S,2R,3S,4R)- and (1R,2S,3R,4S)-2-exo-cyano-3-exo-phenylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylate；[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (1S,2R,3S,4R)-2-cyano-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 142635-89-0；142698-02-0；142698-05-3；142698-08-6
• 化学式: C₂₅H₂₉NO₂
• 分子量: 375.511
• InChiKey: OGKSFIDWHHNQGK-HAXSMTTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  冰片 在 三氯化铝 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， 反应 45.0h， 生成 (-)-(1'S,2'R,4'S)-bornyl (1S,2R,3S,4R)- and (1R,2S,3R,4S)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-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

文献信息

• Asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with cyclopentadiene
  作者：Carlos Cativiela、Jose A. Mayoral、Alberto Avenoza、Jesus M. Peregrina、Fernando J. Lahoz、Sergio Gimeno

  DOI：10.1021/jo00043a025

  日期：1992.8

  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.