2-[6-(2-Chloroethyl)-1,3-benzodioxol-5-yl]cyclohex-2-en-1-one | 1238587-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-[6-(2-Chloroethyl)-1,3-benzodioxol-5-yl]cyclohex-2-en-1-one
• CAS: 1238587-86-4
• 化学式: C₁₅H₁₅ClO₃
• 分子量: 278.735
• InChiKey: NVRABHDFABHSAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[6-(2-Chloroethyl)-1,3-benzodioxol-5-yl]cyclohex-2-en-1-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42%的产率得到C₁₅H₁₅NO₃
  参考文献：
  名称：

  One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN₃: Rapid Access to Polycyclic Alkaloids

  摘要：

  A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.

  DOI：

  10.1021/jo101226r
• 作为产物：
  描述：

  [6-(2-chloroethyl)-1,3-benzodioxol-5-yl]boronic acid 、 1-(4-喹啉基)甲胺 在 5% Pd(II)/C(eggshell) 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 2-[6-(2-Chloroethyl)-1,3-benzodioxol-5-yl]cyclohex-2-en-1-one
  参考文献：
  名称：

  One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN₃: Rapid Access to Polycyclic Alkaloids

  摘要：

  A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.

  DOI：

  10.1021/jo101226r

文献信息

• One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN₃: Rapid Access to Polycyclic Alkaloids
  作者：Yu-Ming Zhao、Peiming Gu、Yong-Qiang Tu、Hai-Jun Zhang、Qing-Wei Zhang、Chun-An Fan

  DOI：10.1021/jo101226r

  日期：2010.8.6

  A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.