4-methyl-2-thiophenecyclotriboroxane | 959785-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 有机硼氧烷
• 英文名称: 4-methyl-2-thiophenecyclotriboroxane
• 英文别名: 4-methyl-2-thiopheneboronic anhydride；2,4,6-Tris(4-methylthiophen-2-yl)-1,3,5,2,4,6-trioxatriborinane
• CAS: 959785-70-7
• 化学式: C₁₅H₁₅B₃O₃S₃
• 分子量: 371.913
• InChiKey: GDZHYPJYKTYSBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methyl-2-thiophenecyclotriboroxane 、 4-溴苯甲酰苯 在 palladium diacetate 、 dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 、 sodium carbonate 作用下， 以 仲丁醇 为溶剂， 反应 16.0h， 以90%的产率得到[4-(4-Methylthiophen-2-yl)phenyl]-phenylmethanone
  参考文献：
  名称：

  Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki–Miyaura reactions

  摘要：

  An efficient synthesis of 4-methyl-2-thiopheneboronic anhydride is reported. Regioselective lithiation of 3-methylthiophene followed by reaction with triisopropylborate and hydrolysis provides a 92:8 ratio of 4-methyl-2-thiopheneboronic acid (1) and regioisomeric 2-methyl-3-thiopheneboronic acid (3). The undesired regioisomer is selectively protodeboronated with concentrated acid to provide only the desired 4-methyl-2-thiopheneboronic acid (1). The title compound is isolated by dehydration/crystallization and employed in several Suzuki-Miyaura reactions. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.060
• 作为产物：
  描述：

  3-甲基噻吩 以84.2%的产率得到4-methyl-2-thiophenecyclotriboroxane
  参考文献：
  名称：

  Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki–Miyaura reactions

  摘要：

  An efficient synthesis of 4-methyl-2-thiopheneboronic anhydride is reported. Regioselective lithiation of 3-methylthiophene followed by reaction with triisopropylborate and hydrolysis provides a 92:8 ratio of 4-methyl-2-thiopheneboronic acid (1) and regioisomeric 2-methyl-3-thiopheneboronic acid (3). The undesired regioisomer is selectively protodeboronated with concentrated acid to provide only the desired 4-methyl-2-thiopheneboronic acid (1). The title compound is isolated by dehydration/crystallization and employed in several Suzuki-Miyaura reactions. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.060

文献信息

• Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki–Miyaura reactions
  作者：Liane M. Klingensmith、Matthew M. Bio、George A. Moniz

  DOI：10.1016/j.tetlet.2007.09.060

  日期：2007.11

  An efficient synthesis of 4-methyl-2-thiopheneboronic anhydride is reported. Regioselective lithiation of 3-methylthiophene followed by reaction with triisopropylborate and hydrolysis provides a 92:8 ratio of 4-methyl-2-thiopheneboronic acid (1) and regioisomeric 2-methyl-3-thiopheneboronic acid (3). The undesired regioisomer is selectively protodeboronated with concentrated acid to provide only the desired 4-methyl-2-thiopheneboronic acid (1). The title compound is isolated by dehydration/crystallization and employed in several Suzuki-Miyaura reactions. (C) 2007 Elsevier Ltd. All rights reserved.