2-(4'-carboxyphenyl)benzothiazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4'-carboxyphenyl)benzothiazoline
• 英文别名: 4-(2,3-Dihydro-1,3-benzothiazol-2-yl)benzoic acid
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: HZXBHQWYUKJYDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对醛基苯甲酸 、 2-氨基苯硫醇 以 乙醇 为溶剂， 生成 2-(4'-carboxyphenyl)benzothiazoline
  参考文献：
  名称：

  苯并噻唑啉作为高效还原剂对α-氨基酯的对映选择性有机催化转移加氢

  摘要：

  苯并噻唑啉用作手性磷酸催化的α-亚氨基酯转移加氢的有效和通用的还原剂。相应的α-氨基酯具有优异的对映选择性。还研究了带有羟基的新颖且易于除去的苯并噻唑啉。

  DOI：

  10.1002/adsc.201000328
• 作为试剂：
  描述：

  苯甲酰甲酸甲酯 、 甲氧苯胺 在 2-(4'-carboxyphenyl)benzothiazoline 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 methyl 2-((4-methoxyphenyl)amino)-2-phenylacetate
  参考文献：
  名称：

  Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor

  摘要：

  A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline and benzothiazole by washing with aqueous basic solution. The present approach provides a convenient and straightforward access to various amines with broad substrate scope and in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.061

文献信息

• Enantioselective Organocatalytic Transfer Hydrogenation of α‐Imino Esters by Utilization of Benzothiazoline as Highly Efficient Reducing Agent
  作者：Chen Zhu、Takahiko Akiyama

  DOI：10.1002/adsc.201000328

  日期：2010.10.9

  Benzothiazoline was employed as an efficient and versatile reducing agent for the chiral phosphoric acid-catalyzed transfer hydrogenation of α-imino esters. The corresponding α-amino esters were furnished with excellent enantioselectivities. Novel and readily removable benzothiazolines bearing a hydroxy group were also investigated.

  苯并噻唑啉用作手性磷酸催化的α-亚氨基酯转移加氢的有效和通用的还原剂。相应的α-氨基酯具有优异的对映选择性。还研究了带有羟基的新颖且易于除去的苯并噻唑啉。
• Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor
  作者：Chen Zhu、Takahiko Akiyama

  DOI：10.1016/j.tetlet.2011.11.061

  日期：2012.1

  A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline and benzothiazole by washing with aqueous basic solution. The present approach provides a convenient and straightforward access to various amines with broad substrate scope and in good yields. (C) 2011 Elsevier Ltd. All rights reserved.