5-(3-hydroxy-benzo[b]thiophen-2-yl)-5-oxo-3-phenyl-pentanoic acid | 1204400-33-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 5-(3-hydroxy-benzo[b]thiophen-2-yl)-5-oxo-3-phenyl-pentanoic acid
• 英文别名: 5-(3-Hydroxy-1-benzothiophen-2-yl)-5-oxo-3-phenylpentanoic acid
• CAS: 1204400-33-8
• 化学式: C₁₉H₁₆O₄S
• 分子量: 340.4
• InChiKey: FPFVCSMFTLSKSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 5-(3-hydroxy-benzo[b]thiophen-2-yl)-5-oxo-3-phenyl-pentanoic acid 在 samarium(III) chloride 作用下， 反应 72.0h， 以97%的产率得到5-(3-hydroxy-benzo[b]thiophen-2-yl)-5-oxo-3-phenyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Highly Chemoselective Esterification Reactions and Boc/THP/TBDMS Discriminating Deprotections under Samarium(III) Catalysis

  摘要：

  The usefulness of SmCl(3) as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.

  DOI：

  10.1021/ol200247c
• 作为产物：
  描述：

  2,2-二硫二苯甲酰氯 、 5-phenyl-cyclohexane-1,3-dione 在 samarium(III) chloride 、 三乙胺 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以43%的产率得到5-(3-hydroxy-benzo[b]thiophen-2-yl)-5-oxo-3-phenyl-pentanoic acid
  参考文献：
  名称：

  As many as six tandem reactions in one step! Unprecedented formation of highly functionalized benzothiophenes

  摘要：

  讨论了一种涉及1,3-二酮和2,2′-二硫代二苯甲酰氯的新颖反应途径，该途径可用于合成具有螺环缩酮、内酯、羰基、羟基和羧酸功能的苯并噻吩。

  DOI：

  10.1039/b914424b

文献信息

• As many as six tandem reactions in one step! Unprecedented formation of highly functionalized benzothiophenes
  作者：Pushparathinam Gopinath、Surapaneni Nilaya、Tripathy Ranjan Debi、Venkatachalam Ramkumar、Kannoth Manheri Muraleedharan

  DOI：10.1039/b914424b

  日期：——

  A novel reaction pathway involving 1,3-diketones and 2,2′-dithiodibenzoylchloride that gives access to benzothiophenes with spiroketal, lactone, carbonyl, hydroxyl and carboxylic acid functionalities is discussed.

  讨论了一种涉及1,3-二酮和2,2′-二硫代二苯甲酰氯的新颖反应途径，该途径可用于合成具有螺环缩酮、内酯、羰基、羟基和羧酸功能的苯并噻吩。
• Highly Chemoselective Esterification Reactions and Boc/THP/TBDMS Discriminating Deprotections under Samarium(III) Catalysis
  作者：Pushparathinam Gopinath、Surapaneni Nilaya、Kannoth Manheri Muraleedharan

  DOI：10.1021/ol200247c

  日期：2011.4.15

  The usefulness of SmCl(3) as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.