(1S,1R)-(+)-1-phenyl-2-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline | 201797-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1S,1R)-(+)-1-phenyl-2-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1S)-1-phenyl-2-[(1R)-1-phenylethyl]-3,4-dihydro-1H-isoquinoline
• CAS: 201797-10-6
• 化学式: C₂₃H₂₃N
• 分子量: 313.442
• InChiKey: PJNZAWHXLXNNJW-JPYJTQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,1R)-(+)-1-phenyl-2-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  An Enantioselective Access to 1-Alkyl-1,2-Dihydroisoquinolines and 1-Alkyl-, 3-Alkyl-, and 1,3-Dialkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  New chiral isoquinolinium salt derivatives 1, 2 or 3 have been treated with Grignard reagents to give as major products, 1-substituted 1,2-dihydroisoquinolines 4a-f, oxazolidine derivatives 10a-f or 21, respectively, in good yield and in moderate to good diastereoisomeric excess. The stereochemistry of these new derivatives has been elucidated, in particular, by X-ray crystallographic studies of 1,2-dihydroisoquinoline 4b and the minor oxazolidine 11b. Reduction of all these intermediates gave chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines such as base 8. The enantioselective synthesis of the natural alkaloid (-)-salsonidine in three steps and 38% overall yield from salt 3 is described as an application. Reduction of salt 2 gave a new oxazolidine derivative 15 which is a practical intermediate for the synthesis of 3-alkyl 1,2,3,4-tetrahydroisquinolines 17a,b, while oxazolidines such as 10 are convenient precursors of 1,3-disubstituted tetrahydroisoquinolines, as illustrated by a synthesis of 1,3-dimethyl tetrahydroisoquinoline 20.

  DOI：

  10.1021/jo970768a
• 作为产物：
  描述：

  (1S,1R)-(+)-1-phenyl-2-(1-phenylethyl)-1,2-dihydroisoquinoline 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 (1S,1R)-(+)-1-phenyl-2-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  An Enantioselective Access to 1-Alkyl-1,2-Dihydroisoquinolines and 1-Alkyl-, 3-Alkyl-, and 1,3-Dialkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  New chiral isoquinolinium salt derivatives 1, 2 or 3 have been treated with Grignard reagents to give as major products, 1-substituted 1,2-dihydroisoquinolines 4a-f, oxazolidine derivatives 10a-f or 21, respectively, in good yield and in moderate to good diastereoisomeric excess. The stereochemistry of these new derivatives has been elucidated, in particular, by X-ray crystallographic studies of 1,2-dihydroisoquinoline 4b and the minor oxazolidine 11b. Reduction of all these intermediates gave chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines such as base 8. The enantioselective synthesis of the natural alkaloid (-)-salsonidine in three steps and 38% overall yield from salt 3 is described as an application. Reduction of salt 2 gave a new oxazolidine derivative 15 which is a practical intermediate for the synthesis of 3-alkyl 1,2,3,4-tetrahydroisquinolines 17a,b, while oxazolidines such as 10 are convenient precursors of 1,3-disubstituted tetrahydroisoquinolines, as illustrated by a synthesis of 1,3-dimethyl tetrahydroisoquinoline 20.

  DOI：

  10.1021/jo970768a