2-(2,4-Dichloro-phenyl)-1-thiophen-2-yl-ethanone | 188848-22-8

• 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-(2,4-Dichloro-phenyl)-1-thiophen-2-yl-ethanone
• 英文别名: 2-(2,4-Dichlorophenyl)-1-thiophen-2-ylethanone
• CAS: 188848-22-8
• 化学式: C₁₂H₈Cl₂OS
• 分子量: 271.167
• InChiKey: UCVZWHDNRSWFML-UHFFFAOYSA-N

物化性质

• 沸点：
  402.2±35.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,4-Dichloro-phenyl)-1-thiophen-2-yl-ethanone 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-[2-(2,4-Dichloro-phenyl)-1-thiophen-2-yl-ethyl]-1H-imidazole
  参考文献：
  名称：

  Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane

  摘要：

  Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyl-diimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.

  DOI：

  10.1016/s0223-5234(97)87541-1
• 作为产物：
  描述：

  噻吩 、 2,4-二氯苯乙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以66%的产率得到2-(2,4-Dichloro-phenyl)-1-thiophen-2-yl-ethanone
  参考文献：
  名称：

  Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane

  摘要：

  Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyl-diimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.

  DOI：

  10.1016/s0223-5234(97)87541-1

文献信息

• Pd-catalyzed synthesis of α-aryl ketones through couplings of α-arylacetyl chlorides with triarylbismuths as multi-coupling nucleophiles
  作者：Maddali L.N. Rao、Somnath Giri、Deepak N. Jadhav

  DOI：10.1016/j.tetlet.2009.08.074

  日期：2009.11

  The cross-coupling reaction of alpha-arylacetyl chlorides with triarylbismuths was studied under Pd-catalyzed conditions. The reaction was found to be facile under the established protocol and furnished high yields of alpha-aryl ketones in short reaction times. This work also demonstrated a facile synthesis of various regio-isomeric mono-, di- and tri-substituted alpha-aryl ketones in high yields. Triarylbisrnuths were employed as sub-stoichiometric multi-coupling organometallic nucleophiles in this coupling protocol. (C) 2009 Elsevier Ltd. All rights reserved.