N-[(1R,2S,3R,4S)-3-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-4-methylbenzenesulfonamide | 146310-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(1R,2S,3R,4S)-3-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-4-methylbenzenesulfonamide
• CAS: 146310-97-6
• 化学式: C₁₇H₂₅NO₃S
• 分子量: 323.456
• InChiKey: VHUZYKPEGPSTHX-ANQUJSFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1R,2S,3R,4S)-3-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-4-methylbenzenesulfonamide 在 吡啶 、 LiAlH(OCEt₃)3 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(1S,2R,3S,4R)-4,7,7-trimethyl-3-[(4-methylphenyl)sulfonylamino]-2-bicyclo[2.2.1]heptanyl] (2R)-2-hydroxypropanoate
  参考文献：
  名称：

  .alpha.-(Arylsulfonamido)borneols as auxiliaries in asymmetric synthesis: an efficient and highly stereoselective method for the reduction of .alpha.-keto esters

  摘要：

  A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.

  DOI：

  10.1021/jo00057a004
• 作为产物：
  描述：

  exo,exo-2-amino-3-hydroxy-camphor 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(1R,2S,3R,4S)-3-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  .alpha.-(Arylsulfonamido)borneols as auxiliaries in asymmetric synthesis: an efficient and highly stereoselective method for the reduction of .alpha.-keto esters

  摘要：

  A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.

  DOI：

  10.1021/jo00057a004