(1R,2R,7R,8R)-1-Isopropenyl-7,8-epoxy-8,12-dimethyl-11-cyclotetradecen-3-yn-2-ol | 149883-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R,2R,7R,8R)-1-Isopropenyl-7,8-epoxy-8,12-dimethyl-11-cyclotetradecen-3-yn-2-ol
• CAS: 149883-83-0
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: ZBSUWABAVJPDKF-WNPBSCRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-α-甲氧基苯乙酸 、 (1R,2R,7R,8R)-1-Isopropenyl-7,8-epoxy-8,12-dimethyl-11-cyclotetradecen-3-yn-2-ol 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以66%的产率得到(R)-Methoxy-phenyl-acetic acid (E)-(1R,6R,7R,14R)-7-isopropenyl-10,14-dimethyl-15-oxa-bicyclo[12.1.0]pentadec-10-en-4-yn-6-yl ester
  参考文献：
  名称：

  Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization

  摘要：

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.

  DOI：

  10.1021/jo00067a024
• 作为产物：
  描述：

  (1RS,2SR,7R,8R,11E)-1-Isopropenyl-7,8-epoxy-8,12-dimethyl-11-cyclotetradecen-3-yn-2-ol 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 13.0h， 生成 (1R,2R,7R,8R)-1-Isopropenyl-7,8-epoxy-8,12-dimethyl-11-cyclotetradecen-3-yn-2-ol
  参考文献：
  名称：

  Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization

  摘要：

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.

  DOI：

  10.1021/jo00067a024