(1S,2R,4R,SS)-2-hydroxy-10-bornanesulfinamide | 253665-39-3

• 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,4R,SS)-2-hydroxy-10-bornanesulfinamide
• 英文别名: (1S,2R,4R,S_S)-2-hydroxy-10-bornanesulfinamide
• CAS: 253665-39-3
• 化学式: C₁₀H₁₉NO₂S
• 分子量: 217.332
• InChiKey: FPFQYKQXZDLTMF-ACBRSEEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  1.0
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-氯苯甲醛 、 (1S,2R,4R,SS)-2-hydroxy-10-bornanesulfinamide 在 titanium(IV) tetraethanolate 作用下， 以77%的产率得到((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfinic acid 1-(3-chloro-phenyl)-meth-(E)-ylideneamide
  参考文献：
  名称：

  Addition of dienolates to sulfinimines. Stereoselective synthesis of dihydropyridones

  摘要：

  The vinylogous Mannich reaction of sulfinimines with dienolates was investigated. Lithium and trimethylsilyl enolates of ethyl 3-ethoxycrotonate reacted with enantiopure 10-isobornylsulfinimines to give derivatives of delta -aminoacids which were cyclised to 6-aryl substituted derivatives of 2(1H)-pyridinones. 6-Aryl substituted 2,4-piperidinediones with either (S) or (R) configuration were analogously obtained using lithium and TMS enolates of 2,2,6-trimethyl-1,3-dioxin-4-one. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00833-x
• 作为产物：
  描述：

  (+)-10-camphorsulfinic acid 在 盐酸 、 sodium tetrahydroborate 、 lithium amide 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.33h， 生成 (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