(-)-(1S,2R,4S)-bornyl (E)-2-cyanocinnamate | 142635-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (-)-(1S,2R,4S)-bornyl (E)-2-cyanocinnamate
• 英文别名: [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (E)-2-cyano-3-phenylprop-2-enoate
• CAS: 142635-86-7
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: YXHRUDAPWZAFPY-YODYGDNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰乙腈 、 (-)-(1S,2R,4S)-bornyl (E)-2-cyanocinnamate 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 2-amino-3-<(-)-(1'S,2'R,4'S)-bornyloxycarbonyl>-5-cyano-(4R),6-diphenyl-4H-pyran 、 2-amino-3-<(-)-(1'S,2'R,4'S)-bornyloxycarbonyl>-5-cyano-(4S),6-diphenyl-4H-pyran
  参考文献：
  名称：

  Stereocontrolled routes to derivatives of 3-alkoxycarbonyl-2-amino-4-aryl-5-cyano-6-phenyl-4H-pyrans

  摘要：

  The asymmetric Michael addition of cyanoacetates 2b-e and benzoylacetonitrile 6 to alpha-benzoylcinnamonitrile 3 and alpha-cyanocinnamates 7b-e, respectively, has been studied. The resulting 3-alkoxycarbonyl-2-amino-4-aryl-5-cyano-6-phenyl-4H-pyrans 4b-e have been obtained in moderate diastereomeric excess and good chemical yield.

  DOI：

  10.1016/0957-4166(94)00382-l
• 作为产物：
  描述：

  冰片 、 (E)-α-cyanocinnamic 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84%的产率得到(-)-(1S,2R,4S)-bornyl (E)-2-cyanocinnamate
  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

• Cativela C., Diaz-de-Villegas M. D., Galvez J. A., An. Quim., 88 (1992) N 3, S 390-391
  作者：Cativela C., Diaz-de-Villegas M. D., Galvez J. A.

  DOI：——

  日期：——