ethyl 2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxylate | 945454-01-3

• 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: ethyl 2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxylate
• 英文别名: N'-[1-(2-chloro-5-nitrophenyl)ethylidene]ethoxycarbohydrazide；Ethyl 2-[1-(2-chloro-5-nitrophenyl)ethylidene]hydrazinecarboxylate；ethyl N-[1-(2-chloro-5-nitrophenyl)ethylideneamino]carbamate
• CAS: 945454-01-3
• 化学式: C₁₁H₁₂ClN₃O₄
• 分子量: 285.687
• InChiKey: PANMEJQCBJKLKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxylate 在 氯化亚砜 、 sodium 作用下， 以 水 为溶剂， 反应 24.0h， 生成 2-methoxy-5-nitrobenzo[b]thiophene
  参考文献：
  名称：

  A convenient synthesis of benzo[b]chalcogenophenes from 4-(2-chloro-5-nitrophenyl)-1,2,3-chalcogenadiazoles

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.04.077
• 作为产物：
  描述：

  2-氯-5-硝基苯乙酮 、 肼基甲酸乙酯 以 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 2-(1-(2-chloro-5-nitrophenyl)ethylidene)hydrazinecarboxylate
  参考文献：
  名称：

  有机氧化合物的体外活性：II。2-氨基苯并[b]噻吩对K562和HeLa肿瘤细胞系的细胞毒作用

  摘要：

  摘要 研究了一些在第二位具有叔氨基的苯并[ b ]噻吩的体外抗肿瘤活性，该药物对红白血病（K562）和宫颈癌（HeLa）细胞系具有抗性。

  DOI：

  10.1134/s107036322011033x

文献信息

• A convenient approach towards 2- and 3-aminobenzo[b]thiophenes
  作者：Dmitry A. Androsov、Andrey Y. Solovyev、Mikhail L. Petrov、Ray J. Butcher、Jerry P. Jasinski

  DOI：10.1016/j.tet.2010.01.069

  日期：2010.3

  Reaction of 1-(2-chloro-5-nitrophenyl)ethanone via Willgerodt-Kindler route with primary or secondary amines and Sulfur allows a simple, efficient one-pot synthesis of 3-aminobenzo[b]thiophenes. Base-catalyzed transformation of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole in the presence of primary and secondary amines offers a convenient approach towards 2-aminobenzo[b]thiophenes. (C) 2010 Elsevier Ltd. All rights reserved.
• A New Synthesis of Benzo[<i>b</i>]thiophene-2-thiolates and Their Derivatives <i>via</i> Base-Promoted Transformation of 4-(2-Mercaptophenyl)-1,2,3-thiadiazoles
  作者：Fedor S. Teplyakov、Tatiana G. Vasileva、Mikhail L. Petrov、Dmitry A. Androsov

  DOI：10.1021/ol401981w

  日期：2013.8.2

  A reaction of 4-(2-mercaptophenyl)-1,2,3-thiadiazoles with an oxidant in the presence of 1.1 equiv of base afforded good yields of benzo[4,5]thieno[3,2-d][1,2,3]thiadiazoles via the intramolecular oxidative nucleophilic substitution of a hydrogen (ONHS) pathway. The reaction of 4-(2-mercaptophenyl)-1,2,3-thiadiazoles in the presence of >= 2 equiv of base gave 2-mercaptobenzo[b]thiophenes via an anionic ring-opening/ring-closure pathway.
• In Vitro Activity of Organochalcogen Compounds: II. Cytotoxic Effect of 2-Aminobenzo[b]thiophenes Against K562 and HeLa Tumor Cell Lines
  作者：E. A. Popova、A. A. Kornev、S. V. Shmakov、G. D. Nepochatyi、O. A. Kotyunina、M. L. Petrov、V. M. Boitsov、A. V. Stepakov

  DOI：10.1134/s107036322011033x

  日期：2020.11

  Abstract In vitro antitumor activity of some benzo[b]thiophenes with a tertiary amino group in the second position was studied against erythroleukemia (K562) and cervical carcinoma (HeLa) cell lines.

  摘要 研究了一些在第二位具有叔氨基的苯并[ b ]噻吩的体外抗肿瘤活性，该药物对红白血病（K562）和宫颈癌（HeLa）细胞系具有抗性。
• 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.