(1R,2S,3S,6S,7S)-3-chloromethyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-5-one | 1450753-33-9

• 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: (1R,2S,3S,6S,7S)-3-chloromethyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-5-one
• 英文别名: (1R,2S,3S,6S,7S)-3-chloromethyl-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-5-one
• CAS: 1450753-33-9
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: MKSUCQVNKOFGQQ-XDQCBXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (1S)-2-chloro-1-[(1R,2S,3R,4S)-3-cyanobicyclo[2.2.1]hept-5-en-2-yl]ethyl formate 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以56%的产率得到(1S,2R,3S,4R)-3-[(1S)-2-chloro-1-hydroxyethyl]bicyclo[2.2.1]hept-5-ene-2-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