4-methylphenylsulphonic acid 3-(2-furylthio)propylester | 127505-93-5

• 英文名称: 4-methylphenylsulphonic acid 3-(2-furylthio)propylester
• 英文别名: 3-(furan-2-ylsulfanyl)propyl 4-methylbenzenesulfonate
• CAS: 127505-93-5
• 化学式: C₁₄H₁₆O₄S₂
• 分子量: 312.411
• InChiKey: KSAKELKRUJPWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methylphenylsulphonic acid 3-(2-furylthio)propylester 在 对氯苯异氰酸酯 、 四丁基碘化铵 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 potassium iodide 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 29.0h， 生成 (1S,5R)-2,6-dioxa-11λ4-thia-7-azatricyclo[6.3.0.01,5]undeca-3,7-diene 11-oxide
  参考文献：
  名称：

  Regio- and stereocontrol in the intramolecular nitrile oxide cycloaddition to 2-furylthiol- and 2-furylmethanethiol derivatives.

  摘要：

  A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chain length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yield. Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction. Enantiomerically enriched products (e.e. less-than-or-equal-to 95%) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.

  DOI：

  10.1016/s0040-4020(01)80910-8
• 作为产物：
  描述：

  ethyl 3-(2-furylthio)propanoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-methylphenylsulphonic acid 3-(2-furylthio)propylester
  参考文献：
  名称：

  Regio- and stereocontrol in the intramolecular nitrile oxide cycloaddition to 2-furylthiol- and 2-furylmethanethiol derivatives.

  摘要：

  A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chain length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yield. Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction. Enantiomerically enriched products (e.e. less-than-or-equal-to 95%) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.

  DOI：

  10.1016/s0040-4020(01)80910-8