(2S,3R)-3-(1-hydroxycyclohexyl)-N,N-dimethylbicyclo[2.2.1]hept-5-ene-2-carboxamide | 960215-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-(1-hydroxycyclohexyl)-N,N-dimethylbicyclo[2.2.1]hept-5-ene-2-carboxamide
• CAS: 960215-72-9
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: ILUPOJDUCBKFGS-RFQIPJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(1-hydroxycyclohexyl)-N,N-dimethylbicyclo[2.2.1]hept-5-ene-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以52%的产率得到1-((2R,3S)-3-((dimethylamino)methyl)bicyclo[2.2.1]hept-5-en-2-yl)cyclohexanol
  参考文献：
  名称：

  Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde

  摘要：

  The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. The chiral ligands were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, arylamine and tosyl substituted chiral ligands 9a-d exhibited the highest selectivities (up to 97% ee). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.019
• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 反应 4.33h， 生成 (2S,3R)-3-(1-hydroxycyclohexyl)-N,N-dimethylbicyclo[2.2.1]hept-5-ene-2-carboxamide
  参考文献：
  名称：

  Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde

  摘要：

  The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. The chiral ligands were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, arylamine and tosyl substituted chiral ligands 9a-d exhibited the highest selectivities (up to 97% ee). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.019