(3,5-dichlorophenyl)(thiophen-2-yl)methanone | 1036968-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,5-dichlorophenyl)(thiophen-2-yl)methanone
• 英文别名: (3,5-dichlorophenyl)-thiophen-2-ylmethanone
• CAS: 1036968-25-8
• 化学式: C₁₁H₆Cl₂OS
• 分子量: 257.14
• InChiKey: IDXQZAXIGKDQFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (3,5-dichlorophenyl)(thiophen-2-yl)methanone 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [(Z)-[(3,5-dichlorophenyl)-thiophen-2-ylmethylidene]amino]thiourea
  参考文献：
  名称：

  Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB

  摘要：

  Human African trypanosomiasis ( HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T. brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T. brucei, and specificity was assessed with a panel of four mammalian cell lines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.083
• 作为产物：
  描述：

  2-噻吩甲酸 在 N-甲基吗啉 、 potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (3,5-dichlorophenyl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  可回收的钯催化 Suzuki 偶联芳族三嗪酯：芳酸芳基酮的实用一锅法合成

  摘要：

  摘要 已经开发出一种高效的多相钯催化的芳族三嗪酯与芳基硼酸的 Suzuki 偶联。以 2 mol% 的 MCM-41 键合二齿膦钯配合物 [MCM-41-2P-Pd(OAc) 2 ] 为催化剂，反应在 110 ℃的甲苯中顺利进行，为合成芳基酮从容易获得的芳香酸开始，在一锅法中以中等至极好的收率。MCM-41-2P-Pd(OAc) 2催化剂可重复使用至少七次，其催化活性没有任何明显降低。

  DOI：

  10.1080/00397911.2022.2070766

文献信息

• One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling
  作者：Hongxiang Wu、Baiping Xu、Yue Li、Fengying Hong、Dezhao Zhu、Junsheng Jian、Xiaoer Pu、Zhuo Zeng

  DOI：10.1021/acs.joc.5b02667

  日期：2016.4.1

  A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min.

  已经开发了钯催化的一锅法合成芳基酮。三嗪酸酯与芳基硼酸偶联时，在1 mol％Pd（PPh 3）2 Cl 2存在下30分钟，以中等至极好的收率（高达95％）提供芳基酮。
• Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB
  作者：Jeremy P. Mallari、Anang Shelat、Aaron Kosinski、Conor R. Caffrey、Michele Connelly、Fangyi Zhu、James H. McKerrow、R. Kiplin Guy

  DOI：10.1016/j.bmcl.2008.03.083

  日期：2008.5

  Human African trypanosomiasis ( HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T. brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T. brucei, and specificity was assessed with a panel of four mammalian cell lines. (c) 2008 Elsevier Ltd. All rights reserved.
• Recyclable palladium-catalyzed Suzuki coupling of aromatic triazine esters: A practical one-pot synthesis of aryl ketones from aromatic acids
  作者：Mingzhong Cai、Gang Xie、Zhaotao Xu、Bin Huang

  DOI：10.1080/00397911.2022.2070766

  日期：2022.4.3

  palladium-catalyzed Suzuki coupling of aromatic triazine esters with arylboronic acids has been developed. The reaction proceeds smoothly in toluene at 110 °C using 2 mol% of MCM-41-bound bidentate phosphine palladium complex [MCM-41-2P-Pd(OAc)2] as catalyst and provides a novel and practical method for the synthesis of aryl ketones starting from readily available aromatic acids in a one-pot procedure with

  摘要 已经开发出一种高效的多相钯催化的芳族三嗪酯与芳基硼酸的 Suzuki 偶联。以 2 mol% 的 MCM-41 键合二齿膦钯配合物 [MCM-41-2P-Pd(OAc) 2 ] 为催化剂，反应在 110 ℃的甲苯中顺利进行，为合成芳基酮从容易获得的芳香酸开始，在一锅法中以中等至极好的收率。MCM-41-2P-Pd(OAc) 2催化剂可重复使用至少七次，其催化活性没有任何明显降低。