ω-(4-formylphenoxy)-4-chloroacetophenone | 901414-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-(4-formylphenoxy)-4-chloroacetophenone
• 英文别名: 4-[2-(4-Chlorophenyl)-2-oxoethoxy]benzaldehyde
• CAS: 901414-37-7
• 化学式: C₁₅H₁₁ClO₃
• mdl: MFCD03361598
• 分子量: 274.704
• InChiKey: DJCHDCNJGUJKCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ω-(4-formylphenoxy)-4-chloroacetophenone 、 3-phenyl-4-thioxo-2-thiazolidinone 在 sodium acetate 、 溶剂黄146 作用下， 反应 0.5h， 以72%的产率得到5-[4-(2-(4-chlorophenyl)-2-oxoethoxy)benzylidene]-3-phenyl-4-thioxo-2-thiazolidinone
  参考文献：
  名称：

  一些新的5-取代-3-苯基-4-硫代-2-噻唑烷酮及其稠合噻唑并[2,3-d]噻唑衍生物的合成

  摘要：

  新的 5-arylmethylene-3-phenyl-4-thioxo-2-thiazolidinone 衍生物是通过 ω-(4-formylphenoxy) acetophenone 衍生物与 3-phenyl-4-thioxo-2-thiazolidinone 缩合合成的，收率很好。研究了新合成的化合物与 N-芳基马来酰亚胺、丙烯酸乙酯和 ω-硝基苯乙烯的环加成反应。在热反应条件下，[4+2] 环加成以完全的位点和区域选择性进行，以产生新的稠合噻唑并 [2,3-d] 噻唑衍生物。图形概要

  DOI：

  10.1080/17415993.2015.1065405
• 作为产物：
  描述：

  对氯苯乙酮 在 对甲苯磺酸 、 1,3-二溴咪唑烷-2,4-二酮 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 ω-(4-formylphenoxy)-4-chloroacetophenone
  参考文献：
  名称：

  Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents

  摘要：

  Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 mu g/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 mu g/mL and 4 mu g/mL) and 64-fold more activity than oxacillin (MIC > 64 mu g/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 mu g/mL, and 64-fold more potency than norfloxacin (MIC > 64 mu g/mL) and comparable activity to oxacillin (MIC = 1 mu g/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.023

文献信息

• A Convenient Synthesis of Some New 5-Substituted-4-Thioxo-Thiazolidinones and Fused Thiopyrano[2,3-<i>d</i>]thiazole Derivatives
  作者：Nadia Hanafy Metwally

  DOI：10.1080/10426500701849105

  日期：2008.8.4

  Z-5-arylmethylene-4-thioxo-thiazolidine derivatives have been synthesized by condensation of ω -(4-formylphenoxy)acetophenone derivatives with 4-thioxo-thiazolidine derivatives, in good yields. The cycloaddition of the newly synthesized compounds to N-arylmaleimides, N-phenyl-1,2,4-triazole-3,5-dione, ethyl acrylate and ω -nitrostyrene has been studied. Under thermal reaction conditions [4 + 2] cycloaddition proceeds

  新的 Z-5-arylmethylene-4-thioxo-thiazolidine 衍生物是通过 ω -(4-formylphenoxy) acetophenone 衍生物与 4-thioxo-thiazolidine 衍生物缩合合成的，收率良好。研究了新合成的化合物与 N-芳基马来酰亚胺、N-苯基-1,2,4-三唑-3,5-二酮、丙烯酸乙酯和 ω-硝基苯乙烯的环加成反应。在热反应条件下，[4 + 2] 环加成以完全的位点和区域选择性进行，以产生新的稠合噻喃并 [2,3-d] 噻唑衍生物。
• Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents
  作者：Ming-Xia Song、Chang-Ji Zheng、Xian-Qing Deng、Qing Wang、Shao-Pu Hou、Ting-Ting Liu、Xiao-Lan Xing、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.05.023

  日期：2012.8

  Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 mu g/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 mu g/mL and 4 mu g/mL) and 64-fold more activity than oxacillin (MIC > 64 mu g/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 mu g/mL, and 64-fold more potency than norfloxacin (MIC > 64 mu g/mL) and comparable activity to oxacillin (MIC = 1 mu g/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of some new 5-substituted-3-phenyl-4-thioxo-2-thiazolidinones and their fused thiopyrano[2,3-<i>d</i>]thiazole derivatives
  作者：Mohamed Ahmed Badawy、Nadia Hanafy Metwally、Doha Samir Okpy

  DOI：10.1080/17415993.2015.1065405

  日期：2015.9.3

  5-arylmethylene-3-phenyl-4-thioxo-2-thiazolidinone derivatives have been synthesized by condensation of ω-(4-formylphenoxy)acetophenone derivatives with 3-phenyl-4-thioxo-2-thiazolidinone, in good yields. The cycloaddition of the newly synthesized compounds to N-arylmaleimides, ethyl acrylate and ω-nitrostyrene has been studied. Under thermal reaction conditions [4+2] cycloaddition proceeds with complete site-

  新的 5-arylmethylene-3-phenyl-4-thioxo-2-thiazolidinone 衍生物是通过 ω-(4-formylphenoxy) acetophenone 衍生物与 3-phenyl-4-thioxo-2-thiazolidinone 缩合合成的，收率很好。研究了新合成的化合物与 N-芳基马来酰亚胺、丙烯酸乙酯和 ω-硝基苯乙烯的环加成反应。在热反应条件下，[4+2] 环加成以完全的位点和区域选择性进行，以产生新的稠合噻唑并 [2,3-d] 噻唑衍生物。图形概要