2-<(furylmethyl)thio>-1-nitrobutane | 135082-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-<(furylmethyl)thio>-1-nitrobutane
• 英文别名: 2-(1-nitrobutan-2-ylsulfanylmethyl)furan
• CAS: 135082-19-8
• 化学式: C₉H₁₃NO₃S
• 分子量: 215.273
• InChiKey: XHWVJPBMFNNBJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<(furylmethyl)thio>-1-nitrobutane 在 对氯苯异氰酸酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以78%的产率得到(3aR,8aR)-6-Ethyl-3aH,6H-furo[2,3-d]thieno[3,4-c]isoxazole
  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：

  硝基甲烷 、 糠基硫醇 、 丙醛 在 哌啶 作用下， 以78%的产率得到2-<(furylmethyl)thio>-1-nitrobutane
  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