ethyl 4-(2-chloro-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate | 1392224-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 4-(2-chloro-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate
• 英文别名: Ethyl 4-(2-chloro-5-ethenylsulfanyl-4-nitrothiophen-3-yl)piperazine-1-carboxylate；ethyl 4-(2-chloro-5-ethenylsulfanyl-4-nitrothiophen-3-yl)piperazine-1-carboxylate
• CAS: 1392224-25-7
• 化学式: C₁₃H₁₆ClN₃O₄S₂
• 分子量: 377.873
• InChiKey: AJBVYNULWUZMGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-chloro-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 4-(2-formyl-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

  摘要：

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

  DOI：

  10.3987/com-12-s(n)108
• 作为产物：
  描述：

  1-哌嗪羧酸乙酯盐酸盐 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 ethyl 4-(2-chloro-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, Part 11: ipso-Formylation of 2-Chlorothiophenes under Vilsmeier-Haack Conditions

  摘要：

  在Vilsmeier-Haack条件下，对电子丰富、3,4-推拉取代的2-氯噻吩进行了区域选择性的异位甲酰化反应，并以较好的产率获得了产物。通过使用不同的卤代噻吩、氯代苯胺和1-甲基-3-氯吲哚，探索了这一新反应的合成范围。与它们的C-H结构类似物相比，氯化的噻吩、苯胺和吲哚对氯甲基亚胺盐的亲电攻击表现出较低的活性。

  DOI：

  10.1515/znb-2012-0402

文献信息

• Chemistry of Polyhalogenated Nitrobutadienes, Part 11: ipso-Formylation of 2-Chlorothiophenes under Vilsmeier-Haack Conditions
  作者：Eva-Janina Vogt、Viktor A. Zapolskii、Eva Nutz、Dieter E. Kaufmann

  DOI：10.1515/znb-2012-0402

  日期：2012.4.1

  The regioselective ipso-formylation of electron-rich, 3,4-push-pull-substituted 2-chlorothiophenes under Vilsmeier-Haack conditions was performed in good yields. The synthetic scope of this new reaction was explored using various halothiophenes, chloroanilines, and 1-methyl-3-chloroindole. In comparison with their structural C-H analogs the chlorinated thiophenes, anilines, and the indole proved to be less reactive toward electrophilic attack by chloromethyleniminium salts.

  在Vilsmeier-Haack条件下，对电子丰富、3,4-推拉取代的2-氯噻吩进行了区域选择性的异位甲酰化反应，并以较好的产率获得了产物。通过使用不同的卤代噻吩、氯代苯胺和1-甲基-3-氯吲哚，探索了这一新反应的合成范围。与它们的C-H结构类似物相比，氯化的噻吩、苯胺和吲哚对氯甲基亚胺盐的亲电攻击表现出较低的活性。

• Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones
  作者：Dieter E. Kaufmann、Viktor A. Zapol'skii、Eva-Janina Vogt、Mimoza Gjikaj

  DOI：10.3987/com-12-s(n)108

  日期：——

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.