2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxamide | 1360685-00-2

• 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-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxamide
• 英文别名: 2'-chloro-5'-nitroacetophenone semicarbazone
• CAS: 1360685-00-2
• 化学式: C₉H₉ClN₄O₃
• 分子量: 256.648
• InChiKey: DBCQBRNYEMIJKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxamide 在 selenium(IV) oxide 、 potassium permanganate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 4-chloro-N,N-diethyl-7-nitrobenzo[b]selenophen-2-amine
  参考文献：
  名称：

  A Novel Synthesis of Benzo[b]selenophenes via Regioselective Intramolecular Transformation of 4-(3-Nitroaryl)-1,2,3-selenadiazoles

  摘要：

  Base-promoted transformation of 4-(3-nitroaryl)-1,2,3-selenadiazoles via intermediate formation of eneselenolates followed by 5-exo-trig cyclization Is reported. The regiochemistry of the intramolecular cyclization is condition-dependent. In the presence of an oxidant, the oxidative nucleophilic substitution of the hydrogen (ONSH, SNArH) pathway, by oxidative aromatization of the rapidly formed sigma(H)-adduct, takes place. In the absence of oxidant, the reaction proceeds via intermediate formation of the sigma(Cl)-adduct, following nucleophilic aromatic substitution of the halogen (SNArCl) pathway.

  DOI：

  10.1021/ol400547n
• 作为产物：
  描述：

  2-氯-5-硝基苯乙酮 、 盐酸氨基脲 以 异丙醇 为溶剂， 以88%的产率得到2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxamide
  参考文献：
  名称：

  New synthesis of 2-aminobenzo[b]selenophenes from 4-(2-chloroaryl)-1,2,3-selenadiazoles

  摘要：

  DOI：

  10.1134/s1070428012010265

文献信息

• A convenient synthesis of benzo[b]chalcogenophenes from 4-(2-chloro-5-nitrophenyl)-1,2,3-chalcogenadiazoles
  作者：Anna G. Lyapunova、Dmitry A. Androsov、Mikhail L. Petrov

  DOI：10.1016/j.tetlet.2013.04.077

  日期：2013.6

  An unusual base-promoted transformation of readily available 4-(2-chloro-5-nitrophenyI)-1,2,3-thia-and selenadiazoles affords a convenient approach toward benzo[b]thiophenes and benzo[b]selenophenes. (C) 2013 Elsevier Ltd. All rights reserved.
• New synthesis of 2-aminobenzo[b]selenophenes from 4-(2-chloroaryl)-1,2,3-selenadiazoles
  作者：M. L. Petrov、A. G. Lyapunova、D. A. Androsov

  DOI：10.1134/s1070428012010265

  日期：2012.1
• A Novel Synthesis of Benzo[<i>b</i>]selenophenes via Regioselective Intramolecular Transformation of 4-(3-Nitroaryl)-1,2,3-selenadiazoles
  作者：Anna G. Lyapunova、Mikhail L. Petrov、Dmitry A. Androsov

  DOI：10.1021/ol400547n

  日期：2013.4.5

  Base-promoted transformation of 4-(3-nitroaryl)-1,2,3-selenadiazoles via intermediate formation of eneselenolates followed by 5-exo-trig cyclization Is reported. The regiochemistry of the intramolecular cyclization is condition-dependent. In the presence of an oxidant, the oxidative nucleophilic substitution of the hydrogen (ONSH, SNArH) pathway, by oxidative aromatization of the rapidly formed sigma(H)-adduct, takes place. In the absence of oxidant, the reaction proceeds via intermediate formation of the sigma(Cl)-adduct, following nucleophilic aromatic substitution of the halogen (SNArCl) pathway.