(1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-ethynylsulfanyl-1,7,7-trimethylbicyclo[2.2.1]heptane | 193414-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-ethynylsulfanyl-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 193414-89-0
• 化学式: C₁₇H₂₈OS
• 分子量: 280.475
• InChiKey: QDUPIEYUGSAOOP-WBOJAVRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-ethynylsulfanyl-1,7,7-trimethylbicyclo[2.2.1]heptane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 91.0h， 生成 9-[(1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo[2.2.1]hep-2-ylsulfanyl]bicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions

  摘要：

  Chiral acetylene thioethers have been prepared in excellent yields from the corresponding thiols. The procedure involves the treatment of the corresponding thiolate with 2-bromo-1,1-diethoxyethane followed by double elimination with LDA and, in some cases, alkylation of the acetylide with alkyl or omega-alkenyl iodides. These compounds have been tested in both intra- and intermolecular Pauson-Khand reactions. This study clearly shows that acetylenic thioethers can be excellent substrates for asymmetric versions of this reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00535-8
• 作为产物：
  描述：

  (1S,2R,3S,4R)-3-(2,2-diethoxyethylsulfanyl)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo[2.2.1]heptane 在 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.0h， 以80%的产率得到(1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-ethynylsulfanyl-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions

  摘要：

  Chiral acetylene thioethers have been prepared in excellent yields from the corresponding thiols. The procedure involves the treatment of the corresponding thiolate with 2-bromo-1,1-diethoxyethane followed by double elimination with LDA and, in some cases, alkylation of the acetylide with alkyl or omega-alkenyl iodides. These compounds have been tested in both intra- and intermolecular Pauson-Khand reactions. This study clearly shows that acetylenic thioethers can be excellent substrates for asymmetric versions of this reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00535-8