2-Chlorbenzoesaeure-5-bromsalicyliden-hydrazon | 41377-45-1

• 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-Chlorbenzoesaeure-5-bromsalicyliden-hydrazon
• 英文别名: 2-chlorobenzoic acid (5-bromo-2-hydroxybenzylidene)hydrazide；ME0259；N-[(5-bromo-2-hydroxyphenyl)methylideneamino]-2-chlorobenzamide
• CAS: 41377-45-1
• 化学式: C₁₄H₁₀BrClN₂O₂
• 分子量: 353.603
• InChiKey: ZBQGQODXTZYKLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chlorbenzoesaeure-5-bromsalicyliden-hydrazon 在 二乙胺基三氟化硫 、 N-heterocyclic carbene 、 lead(IV) tetraacetate 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 反应 2.25h， 生成 (S)-2-(6-bromo-3-(2-chlorophenyl)-1H-inden-1-yl)-1-(2-methoxyphenyl)ethan-1-one
  参考文献：
  名称：

  对映选择性的N-杂环碳烯催化合成功能化的茚

  摘要：

  已发现对映选择性NHC（N-杂环卡宾）催化双官能α，β-不饱和酰基氟和TMS烯醇醚的合成。该反应具有广泛的通用性（31个实例），并且以高水平的对映选择性（大多数> 92：8 er）进行。从机理上讲，该反应可能通过迈克尔/β-内酯化/脱羧序列发生。讨论了衍生化研究及其局限性。

  DOI：

  10.1021/acs.orglett.7b01981
• 作为产物：
  描述：

  5-溴水杨醛 、 2-氯苯甲酰肼 以 乙醇 为溶剂， 生成 2-Chlorbenzoesaeure-5-bromsalicyliden-hydrazon
  参考文献：
  名称：

  对映选择性的N-杂环碳烯催化合成功能化的茚

  摘要：

  已发现对映选择性NHC（N-杂环卡宾）催化双官能α，β-不饱和酰基氟和TMS烯醇醚的合成。该反应具有广泛的通用性（31个实例），并且以高水平的对映选择性（大多数> 92：8 er）进行。从机理上讲，该反应可能通过迈克尔/β-内酯化/脱羧序列发生。讨论了衍生化研究及其局限性。

  DOI：

  10.1021/acs.orglett.7b01981

文献信息

• Statistical molecular design of a focused salicylidene acylhydrazide library and multivariate QSAR of inhibition of type III secretion in the Gram-negative bacterium Yersinia
  作者：Markus K. Dahlgren、Caroline E. Zetterström、Åsa Gylfe、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2010.02.022

  日期：2010.4

  A combined application of statistical molecular design (SMD), quantitative structure-activity relationship (QSAR) modeling and prediction of new active compounds was effectively used to develop salicylidene acylhydrazides as inhibitors of type III secretion (T3S) in the Gram-negative pathogen Yersinia pseudotuberculosis. SMD and subsequent synthesis furnished 50 salicylidene acylhydrazides in high purity. Based on data from biological evaluation in T3S linked assays 18 compounds were classified as active and 25 compounds showed a dose-dependent inhibition. The 25 compounds were used to compute two multivariate QSAR models and two multivariate discriminant analysis models were computed from both active and inactive compounds. Three of the models were used to predict 4416 virtual compounds in consensus and eight new compounds were selected as an external test set. Synthesis and biological evaluation of the test set in Y. pseudotuberculosis and the intracellular pathogen Chlamydia trachomatis validated the models. Y. pseudotuberculosis and C. trachomatis cell-based infection models showed that compounds identified in this study are selective and non-toxic inhibitors of T3S dependent virulence. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Crystal Structures of Two Oxovanadium(V) Complexes with Hydrazone Ligands as Insulin Mimetics
  作者：Zhi-Xi Hang、Xing-Wen Wang、Bo Dong

  DOI：10.1080/15533174.2011.568459

  日期：2011.7.1

  Two mononuclear oxovanadium(V) complexes, [VO(CBB) (OCH3)(CH3OH)] (1) and [VO(HMB)(OCH3)(CH3OH)] (2), where CBB and HMB are the dianionic form of 2-chloro-N'-(5-bromo-2-hydroxybenzylidene) benzohydrazide (H2CBB) and N'-(2-hydroxy-3,5-diiodobenzylidene)-4-methylbenzohydrazide (H2HMB), respectively, were prepared and characterized by IR, elemental analyses, and single crystal X-ray diffraction studies. The crystal of (1) crystallizes in the monoclinic space group C2/c, with a = 27.925(4), b = 7.9382(18), c = 20.018(3) angstrom, beta = 121.690(3)degrees, V = 3775.9(11)angstrom(3), Z = 8. The crystal of (2) crystallizes in the triclinic space group P-1, with a = 7.898(2), b = 10.038(3), c = 13.637(4) angstrom, alpha = 81.874(2), beta = 84.770(2), gamma = 85.288(2)degrees, V = 1063.2(5) angstrom(3), Z = 2. The V atom in each complex is coordinated by ONO donor set of the hydrazone ligand, by one oxo O atom, by one methoxy O atom, and by one methanol O atoms, forming an octahedral coordination.