ethyl 4-cyano-5-iodo-3-methylthiophene-2-carboxylate | 300815-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 4-cyano-5-iodo-3-methylthiophene-2-carboxylate
• CAS: 300815-29-6
• 化学式: C₉H₈INO₂S
• 分子量: 321.139
• InChiKey: VGHCJIJOWXVCJX-UHFFFAOYSA-N

物化性质

• 熔点：
  122-125 °C
• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-cyano-5-iodo-3-methylthiophene-2-carboxylate 在 铜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以41%的产率得到diethyl 3,3'-dicyano-4,4'-dimethyl-2,2'-bithiophene-5,5'-dicarboxylate
  参考文献：
  名称：

  A facile synthesis of α-substituted thiophenes from a functionalized 2-aminothiophene by homo- and cross-coupling reactions

  摘要：

  A series of new a-substituted thiophenes with elongated pi-conjugation are prepared by homo- and cross-coupling reactions. An efficient one-step synthesis of a key intermediate, a substituted 2-iodothiophene, via aprotic diazotization of a Gewald-like 2-aminothiophene is reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.006
• 作为产物：
  描述：

  Ethyl 5-氨基-4-氰基-3-甲基-2-噻吩羧酸乙酯 在 对甲苯磺酸 、 potassium iodide 、 sodium nitrite 作用下， 以 乙腈 、 水 为溶剂， 以73%的产率得到ethyl 4-cyano-5-iodo-3-methylthiophene-2-carboxylate
  参考文献：
  名称：

  A facile synthesis of α-substituted thiophenes from a functionalized 2-aminothiophene by homo- and cross-coupling reactions

  摘要：

  A series of new a-substituted thiophenes with elongated pi-conjugation are prepared by homo- and cross-coupling reactions. An efficient one-step synthesis of a key intermediate, a substituted 2-iodothiophene, via aprotic diazotization of a Gewald-like 2-aminothiophene is reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.006

文献信息

• A facile synthesis of α-substituted thiophenes from a functionalized 2-aminothiophene by homo- and cross-coupling reactions
  作者：Zita Puterová、Anita Andicsová、Ján Moncol、Constantin Rabong、Daniel Végh

  DOI：10.1016/j.tetlet.2009.06.006

  日期：2009.8

  A series of new a-substituted thiophenes with elongated pi-conjugation are prepared by homo- and cross-coupling reactions. An efficient one-step synthesis of a key intermediate, a substituted 2-iodothiophene, via aprotic diazotization of a Gewald-like 2-aminothiophene is reported. (C) 2009 Elsevier Ltd. All rights reserved.