methyl 2-azido-3-(3-chlorophenyl)prop-2-enoate | 944275-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-azido-3-(3-chlorophenyl)prop-2-enoate
• CAS: 944275-74-5
• 化学式: C₁₀H₈ClN₃O₂
• 分子量: 237.645
• InChiKey: FSOCVWUAKGDWLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.06
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3-(3-chlorophenyl)prop-2-enoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Extending the versatility of the Hemetsberger–Knittel indole synthesis through microwave and flow chemistry

  摘要：

  Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.066
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 3-氯苯甲醛 在 甲醇 、 sodium 作用下， 生成 methyl 2-azido-3-(3-chlorophenyl)prop-2-enoate
  参考文献：
  名称：

  Extending the versatility of the Hemetsberger–Knittel indole synthesis through microwave and flow chemistry

  摘要：

  Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.066