5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester | 1227664-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate
• CAS: 1227664-12-1
• 化学式: C₁₈H₂₁BO₄S
• 分子量: 344.239
• InChiKey: UCCHYVZXYUDANO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(2-(Methoxycarbonyl)-5-phenylthiophen-3-yl)boronic acid
  参考文献：
  名称：

  Cyclic amide bioisosterism: Strategic application to the design and synthesis of HCV NS5B polymerase inhibitors

  摘要：

  Conformational modeling has been successfully applied to the design of cyclic bioisosteres used to replace a conformationally rigid amide bond in a series of thiophene carboxylate inhibitors of HCV NS5B polymerase. Select compounds were equipotent with the original amide series. Single-point mutant binding studies, in combination with inhibition structure-activity relationships, suggest this new series interacts at the Thumb-II domain of NS5B. Inhibitor binding at the Thumb-II site was ultimately confirmed by solving a crystal structure of 8b complexed with NS5B. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.008
• 作为产物：
  描述：

  methyl 5-phenylthiophene-2-carboxylate 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 正己烷 为溶剂， 反应 20.0h， 以97%的产率得到5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex

  摘要：

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

  DOI：

  10.1021/jo100352b

文献信息

• Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex
  作者：Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/jo100352b

  日期：2010.6.4

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.
• Cyclic amide bioisosterism: Strategic application to the design and synthesis of HCV NS5B polymerase inhibitors
  作者：Hanbiao Yang、Robert T. Hendricks、Nidhi Arora、Dov Nitzan、Calvin Yee、Matthew C. Lucas、Yanli Yang、Amy Fung、Sonal Rajyaguru、Seth F. Harris、Vincent J.P. Leveque、Julie Q. Hang、Sophie Le Pogam、Deborah Reuter、Gisele A. Tavares

  DOI：10.1016/j.bmcl.2010.06.008

  日期：2010.8

  Conformational modeling has been successfully applied to the design of cyclic bioisosteres used to replace a conformationally rigid amide bond in a series of thiophene carboxylate inhibitors of HCV NS5B polymerase. Select compounds were equipotent with the original amide series. Single-point mutant binding studies, in combination with inhibition structure-activity relationships, suggest this new series interacts at the Thumb-II domain of NS5B. Inhibitor binding at the Thumb-II site was ultimately confirmed by solving a crystal structure of 8b complexed with NS5B. (C) 2010 Elsevier Ltd. All rights reserved.