(1S,2S,3S,4R)-2-butyl-3-[(R)-(4-methylphenyl)sulfinyl]bicyclo[2.2.1]hept-5-ene-2-carbonitrile | 205251-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3S,4R)-2-butyl-3-[(R)-(4-methylphenyl)sulfinyl]bicyclo[2.2.1]hept-5-ene-2-carbonitrile
• CAS: 205251-22-5
• 化学式: C₁₉H₂₃NOS
• 分子量: 313.464
• InChiKey: RRCSNKLIOBPQRP-UVNIEQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R)-2-butyl-3-[(R)-(4-methylphenyl)sulfinyl]bicyclo[2.2.1]hept-5-ene-2-carbonitrile 在 氢氧化钾 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以32%的产率得到(1S,2S,3S,4R)-2-butyl-3-[(R)-(4-methylphenyl)sulfinyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide
  参考文献：
  名称：

  Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles

  摘要：

  The syntheses of enantiomerically pure (Z)-3-p-tolylsulfinylacrylonitrile (1b) and its 2-n-butyl (1a), 2-tert-butyl (1c), and 2-benzyl(ld) derivatives, by stereoselective hydrocyanation with Et2AlCN of their corresponding alkynylsulfoxides, are described. Asymmetric Diels-Alder reactions of these dienophiles with cyclopentadiene are also reported, the most significant finding being their total pi-facial diastereoselectivity, controlled by the sulfur configuration, which can be readily invented by using BF3 as a catalyst. The endo selectivity is very high for Ib under thermal and catalytic (ZnBr2) conditions and complete in the presence of BE3 whereas la and Id only exhibit a complete endo selectivity in the presence of BF3.

  DOI：

  10.1021/jo9721002
• 作为产物：
  描述：

  (+)-(S)-1-hexynyl p-tolyl sulfoxide 在 对苯二酚 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 38.0h， 生成 (1S,2S,3S,4R)-2-butyl-3-[(R)-(4-methylphenyl)sulfinyl]bicyclo[2.2.1]hept-5-ene-2-carbonitrile
  参考文献：
  名称：

  Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles

  摘要：

  The syntheses of enantiomerically pure (Z)-3-p-tolylsulfinylacrylonitrile (1b) and its 2-n-butyl (1a), 2-tert-butyl (1c), and 2-benzyl(ld) derivatives, by stereoselective hydrocyanation with Et2AlCN of their corresponding alkynylsulfoxides, are described. Asymmetric Diels-Alder reactions of these dienophiles with cyclopentadiene are also reported, the most significant finding being their total pi-facial diastereoselectivity, controlled by the sulfur configuration, which can be readily invented by using BF3 as a catalyst. The endo selectivity is very high for Ib under thermal and catalytic (ZnBr2) conditions and complete in the presence of BE3 whereas la and Id only exhibit a complete endo selectivity in the presence of BF3.

  DOI：

  10.1021/jo9721002