(1S,2S)-2-<(Z)-hex-1-enyl>cyclopropane-1-carbonyl azide | 223484-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S)-2-<(Z)-hex-1-enyl>cyclopropane-1-carbonyl azide
• 英文别名: (1S,2S)-2-[(Z)-hex-1-enyl]cyclopropane-1-carbonyl azide
• CAS: 223484-76-2
• 化学式: C₁₀H₁₅N₃O
• 分子量: 193.249
• InChiKey: HBEDTRDPQAGFIW-CDLGPUQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-<(Z)-hex-1-enyl>cyclopropane-1-carbonyl azide 以 苯 为溶剂， 反应 6.0h， 以60%的产率得到3-butyl-2,3-dihydro-H-azepin-2-one
  参考文献：
  名称：

  On the Enantioselectivity of a 2-Aza-divinylcyclopropane Rearrangement

  摘要：

  The optically active cyclopropanecarbonyl azide 6 (ee 90%) was synthesized from the known cyclopropanecarboxylate 4. Upon heating in refluxing benzene, 6 rearranged to the dihydroazepinone 9 (ee 65%) via the isocyanate 7 and the enamide 8. In contrast, the dimethyl-substituted cyclopropanecarbonyl azide 20 rearranged to the isocyanate 21, but decomposed at higher temperatures rather than to undergo Cope rearrangement to 22. The results are consistent with a mechanism involving a boat-like endo-transition state 11 for the rearrangement, which may nor be reached with the dimethyl derivative 21 for steric reasons. The origin of change in enantiomer composition, upon going from 6 to 9, is at present unknown.

  DOI：

  10.1002/(sici)1522-2675(19990310)82:3<315::aid-hlca315>3.0.co;2-t
• 作为产物：
  描述：

  methyl (1S,2S)-2-<(Z)-hex-1-enyl>cyclopropane-1-carboxylate 在 sodium hydroxide 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 (1S,2S)-2-<(Z)-hex-1-enyl>cyclopropane-1-carbonyl azide
  参考文献：
  名称：

  On the Enantioselectivity of a 2-Aza-divinylcyclopropane Rearrangement

  摘要：

  The optically active cyclopropanecarbonyl azide 6 (ee 90%) was synthesized from the known cyclopropanecarboxylate 4. Upon heating in refluxing benzene, 6 rearranged to the dihydroazepinone 9 (ee 65%) via the isocyanate 7 and the enamide 8. In contrast, the dimethyl-substituted cyclopropanecarbonyl azide 20 rearranged to the isocyanate 21, but decomposed at higher temperatures rather than to undergo Cope rearrangement to 22. The results are consistent with a mechanism involving a boat-like endo-transition state 11 for the rearrangement, which may nor be reached with the dimethyl derivative 21 for steric reasons. The origin of change in enantiomer composition, upon going from 6 to 9, is at present unknown.

  DOI：

  10.1002/(sici)1522-2675(19990310)82:3<315::aid-hlca315>3.0.co;2-t