(1S,5R,7R,S_S)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.0^1,5]decane-3-oxide | 178455-82-8

• 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,5R,7R,S_S)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.0^1,5]decane-3-oxide
• 英文别名: (1S,3S,5R,7R)-10,10-dimethyl-4-oxa-3lambda4-thiatricyclo[5.2.1.01,5]decane 3-oxide；(1S,3S,5R,7R)-10,10-dimethyl-4-oxa-3λ4-thiatricyclo[5.2.1.01,5]decane 3-oxide
• CAS: 178455-82-8
• 化学式: C₁₀H₁₆O₂S
• 分子量: 200.302
• InChiKey: MGXOIDBYZVUKFU-PPJAJKPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R,7R,S_S)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.0^1,5]decane-3-oxide 在 lithium amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到(1S,2R,4R,SS)-2-hydroxy-10-bornanesulfinamide
  参考文献：
  名称：

  Facile synthesis of homochiral derivatives of 10-bornane sulfinates, sulfinamides and sulfinimines

  摘要：

  A convenient route for the synthesis of enantiopure 10-bornanesulfinic acid derivatives from (1S)-camphorsulfonyl chloride is described. An interesting epimerization at sulfur in five-membered sultines is observed, leading to diastereoisomerically pure (S-s)-10-isobornyl sulfinates. A large difference in solubility in organic solvents allowed (R-s)-2-oxo-10-bornanesulfinamide to be obtained as the major diastereoisomer. Cyclization of 2-oxo-10-bornanesulfinamides gave five-membered sulfinimines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00433-4
• 作为产物：
  描述：

  (+)-10-camphorsulfinic acid 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.33h， 生成 (1S,5R,7R,S_S)-10,10-dimethyl-4-oxo-3-thiatricyclo[5.2.1.0^1,5]decane-3-oxide
  参考文献：
  名称：

  Facile synthesis of homochiral derivatives of 10-bornane sulfinates, sulfinamides and sulfinimines

  摘要：

  A convenient route for the synthesis of enantiopure 10-bornanesulfinic acid derivatives from (1S)-camphorsulfonyl chloride is described. An interesting epimerization at sulfur in five-membered sultines is observed, leading to diastereoisomerically pure (S-s)-10-isobornyl sulfinates. A large difference in solubility in organic solvents allowed (R-s)-2-oxo-10-bornanesulfinamide to be obtained as the major diastereoisomer. Cyclization of 2-oxo-10-bornanesulfinamides gave five-membered sulfinimines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00433-4

文献信息

• Stereoselective Synthesis of 10-Isobornyl Sulfoxides
  作者：Robert Kawęcki、Zofia Urbańczyk-Lipkowska

  DOI：10.1055/s-1996-4258

  日期：1996.5

  Reaction of organometallic compounds with 10-isobornyl sulfinate 1 leads to 10-isobornyl sulfoxides with high stereoselectivity. This method has been used to prepare homochiral polydentate ligands containing the sulfinyl group.

  有机金属化合物与 10-异冰片烷基亚磺酸酯 1 反应，可生成具有高度立体选择性的 10-异冰片烷基亚砜。这种方法已被用于制备含有亚磺酰基的同手性多齿配体。
• Lewis Acid Mediated Addition of Silyl Ketene Acetals to Sulfinimines
  作者：Robert Kawecki

  DOI：10.1021/jo990913f

  日期：1999.11.1