[2-(2-Chloroethyl)-4,5-dimethoxyphenyl]boronic acid | 1238588-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(2-Chloroethyl)-4,5-dimethoxyphenyl]boronic acid
• CAS: 1238588-06-1
• 化学式: C₁₀H₁₄BClO₄
• 分子量: 244.483
• InChiKey: XZEUAILTWGXLHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(2-Chloroethyl)-4,5-dimethoxyphenyl]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， 反应 5.0h， 以67%的产率得到2-[2-(2-Chloroethyl)-4,5-dimethoxyphenyl]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
• 作为产物：
  描述：

  2-(2-chloroethyl)-4,5-dimethoxybromobenzene 在 正丁基锂 、 硼酸三甲酯 、 盐酸 、 水 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 11.67h， 以92%的产率得到[2-(2-Chloroethyl)-4,5-dimethoxyphenyl]boronic acid
  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.