(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R)-2-[(R)-1-benzylamino-1-(4-methoxyphenyl)methyl]butanoate | 1231169-95-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R)-2-[(R)-1-benzylamino-1-(4-methoxyphenyl)methyl]butanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-[(R)-(benzylamino)-(4-methoxyphenyl)methyl]butanoate
• CAS: 1231169-95-1
• 化学式: C₂₉H₄₁NO₃
• 分子量: 451.649
• InChiKey: GORFBEREJNPSPX-GSQIWVKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苄基-1-(4-甲氧基苯基)甲亚胺 、 (-)-menthyl butyrate 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.67h， 以51%的产率得到(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R)-2-[(R)-1-benzylamino-1-(4-methoxyphenyl)methyl]butanoate
  参考文献：
  名称：

  TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester

  摘要：

  beta-Amino esters were obtained in up to 78% yield with 72:28-96:4 diastereomeric ratios by the reaction of the chiral titanium enolate of menthyl esters, prepared using the TiCl4/Et3N reagent system with prochiral imines. A representative syn-beta-amino ester derivative has been used for the resolution of racemic mandelic acid to obtain a sample with >99% ee in a single step. A representative syn-beta-amino ester was converted to the corresponding N-deprotected amino ester using the Pd-C/HCOOH reagent system, and then to the corresponding beta-amino acid using the glacial CH3COOH/HCl reagent system, and to the corresponding beta-lactam derivative with partial epimerization by the reaction using C2H5MgBr. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.010

文献信息

• TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester
  作者：Mariappan Periasamy、Subramaniapillai Selva Ganesan、Surisetti Suresh

  DOI：10.1016/j.tetasy.2010.02.010

  日期：2010.3

  beta-Amino esters were obtained in up to 78% yield with 72:28-96:4 diastereomeric ratios by the reaction of the chiral titanium enolate of menthyl esters, prepared using the TiCl4/Et3N reagent system with prochiral imines. A representative syn-beta-amino ester derivative has been used for the resolution of racemic mandelic acid to obtain a sample with >99% ee in a single step. A representative syn-beta-amino ester was converted to the corresponding N-deprotected amino ester using the Pd-C/HCOOH reagent system, and then to the corresponding beta-amino acid using the glacial CH3COOH/HCl reagent system, and to the corresponding beta-lactam derivative with partial epimerization by the reaction using C2H5MgBr. (C) 2010 Elsevier Ltd. All rights reserved.