(N)-<(S)-(-)-1-(1-naphthyl)ethyl> (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxamide | 142635-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (N)-<(S)-(-)-1-(1-naphthyl)ethyl> (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxamide
• 英文别名: (1S,2R,3S,4R)-2-cyano-N-[(1S)-1-naphthalen-1-ylethyl]-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide
• CAS: 142635-91-4
• 化学式: C₂₇H₂₄N₂O
• 分子量: 392.5
• InChiKey: QIBMGYBFPXMKGS-AYMCXHNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 (+/-)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到(N)-<(S)-(-)-1-(1-naphthyl)ethyl> (1R,2S,3R,4S)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxamide
  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.