3-(3,4,5-Trimethoxyphenoxy)benzo[b]thiophene | 852050-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3,4,5-Trimethoxyphenoxy)benzo[b]thiophene
• 英文别名: 3-(3,4,5-trimethoxyphenoxy)-1-benzothiophene
• CAS: 852050-26-1
• 化学式: C₁₇H₁₆O₄S
• 分子量: 316.378
• InChiKey: XFVFEMPGGNDXNN-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C
• 沸点：
  439.2±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-Trimethoxyphenoxy)benzo[b]thiophene 、 2-溴苯腈 在 二环己烷并-18-冠醚-6 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以51%的产率得到
  参考文献：
  名称：

  Efficient Access to 2-Aryl-3-Substituted Benzo[b]thiophenes

  摘要：

  Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo [b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.

  DOI：

  10.1021/jo0500378
• 作为产物：
  描述：

  3-溴苯并噻吩亚砜 在 二异丁基氢化铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 3-(3,4,5-Trimethoxyphenoxy)benzo[b]thiophene
  参考文献：
  名称：

  Efficient Access to 2-Aryl-3-Substituted Benzo[b]thiophenes

  摘要：

  Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo [b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.

  DOI：

  10.1021/jo0500378

文献信息

• Efficient Access to 2-Aryl-3-Substituted Benzo[<i>b</i>]thiophenes
  作者：Emilie David、Julie Perrin、Stéphane Pellet-Rostaing、Jérémie Fournier dit Chabert、Marc Lemaire

  DOI：10.1021/jo0500378

  日期：2005.4.1

  Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo [b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.