2-(4-methoxyphenyl)-1-(2-thioxothiazolidin-3-yl)ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-methoxyphenyl)-1-(2-thioxothiazolidin-3-yl)ethanone
• 英文别名: 2-(4-Methoxyphenyl)-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)ethan-1-one；2-(4-methoxyphenyl)-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)ethanone
• 化学式: C₁₂H₁₃NO₂S₂
• 分子量: 267.373
• InChiKey: UKFNNQMHTRPYLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-1-(2-thioxothiazolidin-3-yl)ethanone 、 原甲酸三甲酯 在 2,6-二甲基吡啶 、 [Ni((S)-Tol-BINAP)]OTf₂ 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到(R)-3,3-dimethoxy-2-(4-methoxyphenyl)-1-(2-thioxothiazolidin-3-yl)propan-1-one
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

  摘要：

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.

  DOI：

  10.1021/ja053386s
• 作为产物：
  描述：

  2-巯基噻唑啉 、 4-甲氧基苯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以46%的产率得到2-(4-methoxyphenyl)-1-(2-thioxothiazolidin-3-yl)ethanone
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

  摘要：

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.

  DOI：

  10.1021/ja053386s

文献信息

• Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of <i>N</i>-Acylthiazolidinethiones
  作者：David A. Evans、Regan J. Thomson

  DOI：10.1021/ja053386s

  日期：2005.8.1

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.