2-[2-(3-chlorobenzoyl)-4-methylphenoxy]acetohydrazide | 677707-48-1

• 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-[2-(3-chlorobenzoyl)-4-methylphenoxy]acetohydrazide
• CAS: 677707-48-1
• 化学式: C₁₆H₁₅ClN₂O₃
• 分子量: 318.76
• InChiKey: IDMXGBDCXVODDX-UHFFFAOYSA-N

物化性质

• 熔点：
  177-180 °C
• 沸点：
  596.0±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(3-chlorobenzoyl)-4-methylphenoxy]acetohydrazide 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (3-chlorophenyl)-[5-methyl-2-[(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)methoxy]phenyl]methanone
  参考文献：
  名称：

  Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones

  摘要：

  The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones la-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylarytoxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.005
• 作为产物：
  描述：

  ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到2-[2-(3-chlorobenzoyl)-4-methylphenoxy]acetohydrazide
  参考文献：
  名称：

  微波辅助合成 2-氨基和 2-氮杂环丁烷基 5-(2-苯甲酰基-苯氧基甲基) 1,3,4-恶二唑

  摘要：

  一种简单的高产杂环整合方法，即。二苯甲酮核上的 1,3,4-恶二唑和氮杂环丁烷-2-one 已从取代的 2-羟基二苯甲酮开始，并通过使用温和的条件、湿固体表面和微波辐射开发出来。还说明了这种微波加速反应与常规加热条件的比较。© 2003 Wiley Periodicals, Inc. 杂原子化学 15:37–42, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10210

  DOI：

  10.1002/hc.10210

文献信息

• Microwave-assisted synthesis of 2-amino and 2-azetidinonyl 5-(2-benzoyl-phenoxymethyl) 1,3,4-oxadiazoles
  作者：Shaukath Ara Khanum、S. Shashikanth、B. S. Sudha

  DOI：10.1002/hc.10210

  日期：——

  A simple high yielding method for the integration of heterocyclic rings viz. 1,3,4-oxadiazole and azetidin-2-one at the benzophenone nucleus has been developed starting from substituted 2-hydroxybenzophenones, and by using mild conditions, wet solid surface, and microwave irradiation. A comparison of this microwave-accelerated reaction with conventional heating condition is also illustrated. © 2003

  一种简单的高产杂环整合方法，即。二苯甲酮核上的 1,3,4-恶二唑和氮杂环丁烷-2-one 已从取代的 2-羟基二苯甲酮开始，并通过使用温和的条件、湿固体表面和微波辐射开发出来。还说明了这种微波加速反应与常规加热条件的比较。© 2003 Wiley Periodicals, Inc. 杂原子化学 15:37–42, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10210
• Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles
  作者：V. Girish、Noor Fatima Khanum、H. D. Gurupadaswamy、Shaukath Ara Khanum

  DOI：10.1134/s1068162014030066

  日期：2014.5

  Synthetic pathway of the ten novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles as new potential antimicrobial agents is illustrated. Intramolecular cyclization of 2-(2-aroylaryloxy) aceto hydrazides to 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles was achieved with triethyl orthoformate in good yields. The compounds were characterized by IR, H-1 NMR, mass spectra and by means of CHN analysis. The target compounds were tested for their in vitro antimicrobial activity against representative strains by disc diffusion method and micro dilution methods. Several compounds showed antimicrobial activity comparable with or higher than the standard drugs.
• Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis
  作者：B.R. Vijay Avin、Prabhu Thirusangu、V. Lakshmi Ranganatha、Aiyesha Firdouse、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2014.01.050

  日期：2014.3

  A sequence of coumarin analogs 5a–j was obtained by multi step synthesis from hydroxy benzophenones (1a–j). The in vitro antiproliferative effect of the title compounds was tested against Ehrlich ascites carcinoma (EAC) and Daltons lymphoma ascites (DLA) cell lines. Among the series, compound 5c with bromo group in the benzophenone moiety was endowed with excellent antiproliferative potency with significant

  通过多步合成从羟基二苯甲酮（1a – j）获得了香豆素类似物5a – j的序列。在体外的标题化合物的抗增殖作用是对艾氏腹水癌（EAC）和道尔顿淋巴瘤腹水（DLA）细胞系进行测试。在该系列中，在二苯甲酮部分中具有溴基的化合物5c具有出色的抗增殖潜能，IC 50值很高。此外，化合物5c对鼠EAC和实体DL肿瘤模型系统的体内抗肿瘤作用通过延长的存活期得到证实。复方的抑瘤机制5c是由于抗血管生成和促进细胞凋亡。这些结果表明化合物5c的可能应用，其可以在不久的将来被开发为有效的抗癌药。
• Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones
  作者：Shaukath A. Khanum、Sheena Shashikanth、S. Umesha、R. Kavitha

  DOI：10.1016/j.ejmech.2005.04.005

  日期：2005.11

  The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones la-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylarytoxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively. (c) 2005 Elsevier SAS. All rights reserved.