(1S,4R,RS)-2-oxo-10-bornanesulfinamide | 257875-83-5

• 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,4R,RS)-2-oxo-10-bornanesulfinamide
• 英文别名: (1S,4R,R_S)-2-oxo-10-bornanesulfinamide
• CAS: 257875-83-5
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: LMPOYXQQFRLVMG-KZJPANMKSA-N

物化性质

• 沸点：
  378.9±34.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  60.16
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,4R,RS)-2-oxo-10-bornanesulfinamide 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.03h， 生成 (1S,5R,7R,R_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
• 作为产物：
  描述：

  (+)-10-camphorsulfinic acid 在 氯化亚砜 、 氨 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 (1S,4R,RS)-2-oxo-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

文献信息

• Facile synthesis of homochiral derivatives of 10-bornane sulfinates, sulfinamides and sulfinimines
  作者：Robert Kawęcki

  DOI：10.1016/s0957-4166(99)00433-4

  日期：1999.10

  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.