(7'S,8a'S)-7'-methyl-1,1'-diphenyltetrahydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one | 1260396-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (7'S,8a'S)-7'-methyl-1,1'-diphenyltetrahydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one
• CAS: 1260396-50-6
• 化学式: C₂₅H₂₉NO₂
• 分子量: 375.511
• InChiKey: NRCQWJKOPXBWIH-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 16.0h， 生成 (7'S,8a'S)-7'-methyl-1,1'-diphenyltetrahydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one 、 (7'S,8a'R)-7'-methyl-1,1'-diphenyltetrahydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one
  参考文献：
  名称：

  Straightforward synthesis of [(2S,4R)-1-cyclohexyl-4-methylpiperidin-2-yl]methanol and [(2S,4R)-1-cyclohexyl-4-methylpiperidin-2-yl](diphenyl)methanol: novel chiral ligands for the catalytic addition of diethylzinc to benzaldehyde to give rise to an extensive turn in the sense of asymmetric induction

  摘要：

  Enantiopure [(2S,4R)-1-cyclohexyl-4-methylpiperidin-2-yl]methanol 5a and [(25,4R)-1-cyclohexyl-4-methylpiperidin-2-yl]-(diphenyl)methanol 5b, new beta-amino alcohols based on L-pipecolinic acid (homoproline), have been prepared straightforwardly from rac-alaninol and rac-2-amino-1,1-diphenylpropan-1-ol, respectively. The described route constitutes as a model procedure for the preparation of other related C(4) or/and C(3)-substituted 2-piperidinylmethanols.The new chiral ligands have shown a singular behaviour on the stereocontrol of the benchmark reaction of benzaldehyde and diethylzinc compared with other C(4)-unsubstituted analogues prepared by ourselves from L-pipecolinic acid (compounds 5c, 5d, 5e and 5f). The catalytic activity, the sense of asymmetric induction and the degree of the enantioselectivity depend on the appropriate combination of the substituents on the structural scaffold, but also on the metal-alkoxide involved in the catalysis (zinc or lithium alkoxides). The enantioselective addition of diethylzinc to benzaldehyde mediated by ligands 5a and 5c has been studied with OFT methods. The theoretical evaluation was performed in connection with a working hypothesis based on the different loadings of cis- and trans-catalysts in the reaction medium. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.035