(1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-(hex-1-ynylsulfanyl)-1,7,7-trimethylbicyclo[2.2.1]heptane | 193414-90-3

• 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-(hex-1-ynylsulfanyl)-1,7,7-trimethylbicyclo[2.2.1]heptane
• 英文别名: (1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-3-hex-1-ynylsulfanyl-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 193414-90-3
• 化学式: C₂₁H₃₆OS
• 分子量: 336.582
• InChiKey: WITZAHRLCJDTPB-IKVWTGGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-降冰片二烯 、 (1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-(hex-1-ynylsulfanyl)-1,7,7-trimethylbicyclo[2.2.1]heptane 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吲哚酮 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到4-butyl-5-[(1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo[2.2.1]hept-2-ylsulfanyl]tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-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 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 51.5h， 生成 (1S,2R,3S,4R)-2-(2,2-dimethylpropoxy)-3-(hex-1-ynylsulfanyl)-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

文献信息

• Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions
  作者：Elvira Montenegro、Marta Poch、Albert Moyano、Miquel A Pericàs、Antoni Riera

  DOI：10.1016/s0040-4020(97)00535-8

  日期：1997.6

  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.