6-chloro-6-cyano-1,5-dimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-chloro-6-cyano-1,5-dimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one
• 英文别名: (1S,5S)-6-chloro-1,5-dimethyl-2-oxo-8-oxabicyclo[3.2.1]oct-3-ene-6-carbonitrile
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: NZLPGPXFDGPSOP-XMCUXHSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  6-chloro-6-cyano-1,5-dimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以99%的产率得到(1S,2S,5S)-6-Chloro-2-hydroxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]oct-3-ene-6-carbonitrile
  参考文献：
  名称：

  Synthesis of a 2,7-Dioxatricyclo[4.2.1.0^3,8]nonane:  A Model Study for Possible Application in a Synthesis of Dictyoxetane

  摘要：

  A method for the synthesis of the 2,7-dioxatricyclo[4.2.1.0(3,8)]nonane ring system characteristic of the marine diterpene dictyoxetane has been developed. This method utilizes a dipolar cycloaddition of a 3-oxidopyrylium salt to create the carbon skeleton (Scheme 1) and employs an intramolecular S(N)2 displacement to form the oxetane ring (Schemes 9, 10, 13). The route described could easily be adapted to incorporate additional functionality, making it potentially useful in a total synthesis of dictyoxetane.

  DOI：

  10.1021/jo961680k
• 作为产物：
  描述：

  1-氰乙烯基醋酸盐 、 2-氯丙烯腈 在 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 反应 12.0h， 以30%的产率得到6-chloro-6-cyano-1,5-dimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one
  参考文献：
  名称：

  Synthesis of a 2,7-Dioxatricyclo[4.2.1.0^3,8]nonane:  A Model Study for Possible Application in a Synthesis of Dictyoxetane

  摘要：

  A method for the synthesis of the 2,7-dioxatricyclo[4.2.1.0(3,8)]nonane ring system characteristic of the marine diterpene dictyoxetane has been developed. This method utilizes a dipolar cycloaddition of a 3-oxidopyrylium salt to create the carbon skeleton (Scheme 1) and employs an intramolecular S(N)2 displacement to form the oxetane ring (Schemes 9, 10, 13). The route described could easily be adapted to incorporate additional functionality, making it potentially useful in a total synthesis of dictyoxetane.

  DOI：

  10.1021/jo961680k