(1S)-2-chloro-1-[(1S,6R)-6-cyanocyclohex-3-en-1-yl]ethyl formate | 1450753-23-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S)-2-chloro-1-[(1S,6R)-6-cyanocyclohex-3-en-1-yl]ethyl formate
• 英文别名: [(1S)-2-chloro-1-[(1S,6R)-6-cyanocyclohex-3-en-1-yl]ethyl] formate
• CAS: 1450753-23-7
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: UKOBASAKYQUBTF-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  (1S)-2-chloro-1-[(1S,6R)-6-cyanocyclohex-3-en-1-yl]ethyl formate 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以95%的产率得到(1R,6S)-6-[(2R)-oxiran-2-yl]cyclohex-3-ene-1-carbonitrile
  参考文献：
  名称：

  Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles

  摘要：

  Oxiranyl-substituted cycloalkenecarbonitriles obtained by the Beckmann fragmentation of oximes derived from levoglucosenone adducts with 1,3-butadiene, isoprene, cyclohexadiene, and cyclopentadiene were subjected to Red-Al reduction with opening of the epoxide ring. The reactions with 1,3-butadiene, isoprene, and cyclohexadiene derivatives were accompanied by cyclopropane ring closure and reduction of the cyano group to aldehyde, whereas the cyclopentadiene derivative underwent hydrogenolysis of the oxirane fragment.

  DOI：

  10.1134/s1070428013070051
• 作为产物：
  描述：

  (1S,2S,7R,9R)-10,12-dioxatricyclo[7.2.1.02,7]dodec-4-en-8-one syn-oxime 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到(1S)-2-chloro-1-[(1S,6R)-6-cyanocyclohex-3-en-1-yl]ethyl formate
  参考文献：
  名称：

  Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles

  摘要：

  Oxiranyl-substituted cycloalkenecarbonitriles obtained by the Beckmann fragmentation of oximes derived from levoglucosenone adducts with 1,3-butadiene, isoprene, cyclohexadiene, and cyclopentadiene were subjected to Red-Al reduction with opening of the epoxide ring. The reactions with 1,3-butadiene, isoprene, and cyclohexadiene derivatives were accompanied by cyclopropane ring closure and reduction of the cyano group to aldehyde, whereas the cyclopentadiene derivative underwent hydrogenolysis of the oxirane fragment.

  DOI：

  10.1134/s1070428013070051