3-<(2-furylmethyl)thio>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>propane | 135082-22-3

• 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: 3-<(2-furylmethyl)thio>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>propane
• 英文别名: tert-butyl-[3-(furan-2-ylmethylsulfanyl)propoxy]-dimethylsilane
• CAS: 135082-22-3
• 化学式: C₁₄H₂₆O₂SSi
• 分子量: 286.511
• InChiKey: XGRTVUPBQAHVCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  47.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<(2-furylmethyl)thio>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>propane 、 甲基磺酰氯 、 碘甲烷 生成 Methanesulfonic acid 3-(furan-2-ylmethylsulfanyl)-propyl ester 、 Methanesulfonic acid 3-(1-furan-2-yl-ethylsulfanyl)-propyl ester
  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：

  3-糠硫基丙酸乙酯 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-<(2-furylmethyl)thio>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>propane
  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