N-(2-bromophenyl)thiophene-3-carboxamide | 136341-13-4

• 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: N-(2-bromophenyl)thiophene-3-carboxamide
• CAS: 136341-13-4
• 化学式: C₁₁H₈BrNOS
• mdl: MFCD09935958
• 分子量: 282.161
• InChiKey: DYUCKKPJRKDLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-bromophenyl)thiophene-3-carboxamide 在 四甲基乙二胺 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 水 为溶剂， 以59%的产率得到2-(thiophen-3-yl)benzoxazole
  参考文献：
  名称：

  Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water

  摘要：

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.013
• 作为产物：
  描述：

  3-噻吩甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 N-(2-bromophenyl)thiophene-3-carboxamide
  参考文献：
  名称：

  Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water

  摘要：

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.013

文献信息

• A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists
  作者：S. Alluri、H. Feng、M. Livings、L. Samp、D. Biswas、T.W. Lam、E. Lobkovsky、A.K. Ganguly

  DOI：10.1016/j.tetlet.2011.05.120

  日期：2011.7

  A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol. (C) 2011 Elsevier Ltd. All rights reserved.
• Barbieri, Cristina Lea; Ceraulo, Leopoldo; Maria, Paolo De, Heterocycles, 1991, vol. 32, # 5, p. 975 - 984
  作者：Barbieri, Cristina Lea、Ceraulo, Leopoldo、Maria, Paolo De、Fontana, Antonella、Spinelli, Domenico、Zuppiroli, Luca

  DOI：——

  日期：——
• Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water
  作者：Nekane Barbero、Mónica Carril、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tet.2007.08.013

  日期：2007.10

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.