2-[((R)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-benzoic acid ethyl ester | 175659-83-3

• 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: 2-[((R)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-benzoic acid ethyl ester
• CAS: 175659-83-3
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: WTEDWNJSGKSUPI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[((R)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-benzoic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以90%的产率得到(αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one
  参考文献：
  名称：

  Diastereoselective alkylation of homochiral 1,2,3,4-tetrahydroisoquinolin-3-one. A potential route to enantiomerically pure 4-substituted tetrahydroisoquinolines

  摘要：

  Enantiomerically pure 1,4-dihydroisoquinolin-3-one 1 was prepared in four steps with an overall yield of 60%. Alkylation of the corresponding lactam enolate has been studied and has proven to be highly diastereoselective. Thus, 4-substituted-1,4-dihydroisoquinolin-3-ones 7a-d were obtained in high chemical yields with up to 97% diastereoisomeric excesses.

  DOI：

  10.1016/0957-4166(96)00022-5
• 作为产物：
  描述：

  ethyl 2-(bromomethyl)phenylacetate 、 D-苯甘氨醇 以 乙醇 为溶剂， 以70%的产率得到2-[((R)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-benzoic acid ethyl ester
  参考文献：
  名称：

  Diastereoselective alkylation of homochiral 1,2,3,4-tetrahydroisoquinolin-3-one. A potential route to enantiomerically pure 4-substituted tetrahydroisoquinolines

  摘要：

  Enantiomerically pure 1,4-dihydroisoquinolin-3-one 1 was prepared in four steps with an overall yield of 60%. Alkylation of the corresponding lactam enolate has been studied and has proven to be highly diastereoselective. Thus, 4-substituted-1,4-dihydroisoquinolin-3-ones 7a-d were obtained in high chemical yields with up to 97% diastereoisomeric excesses.

  DOI：

  10.1016/0957-4166(96)00022-5