(1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (R)-pantolactone | 142635-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (R)-pantolactone
• 英文别名: (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylate of (R)-pantolactone；[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1S,2R,3S,4R)-2-cyano-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 142635-90-3
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: JYNKCBLANLYPHC-PLCHWVDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (R)-pantolactone 在 氢氧化钾 、 碘 、 碳酸氢钠 、 potassium iodide 作用下， 生成 (1S,2S,3S,6S,7R,9S)-2-Iodo-5-oxo-9-phenyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-6-carbonitrile
  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
• 作为产物：
  描述：

  D-(-)-泛酰内酯 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， 反应 69.0h， 生成 (1S,2R,3S,4R)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (R)-pantolactone
  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.