(R)-N-methyl-4-(phenyldeuterio)-1,2,3,4-tetrahydroisoquinoline 1-d1 | 213842-75-2

• 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: (R)-N-methyl-4-(phenyldeuterio)-1,2,3,4-tetrahydroisoquinoline 1-d1
• 英文别名: (4R)-4-deuterio-2-methyl-4-phenyl-1,3-dihydroisoquinoline
• CAS: 213842-75-2
• 化学式: C₁₆H₁₇N
• 分子量: 224.31
• InChiKey: NNVATDBGKYTMIL-QKHLJXARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (R)-N-methyl-4-(phenyldeuterio)-1,2,3,4-tetrahydroisoquinoline 1-d1 在 氘代甲醇-d 、 仲丁基锂 、 鹰爪豆碱 作用下， 生成 N-methyl-1,4-dideuterio-4-phenyl-1,2,3,4-tetrahydroisoquinoline 1-d2
  参考文献：
  名称：

  Deracemization of diarylmethanes via lateral lithiation–protonation sequences by means of sparteine

  摘要：

  Deracemization of diarylmethane derivatives was investigated by lateral lithiation-protonation mediated by (-)sparteine. Treatment of racemic 4-phenyltetrahydroisoquinoline 1 with s-butyllithium-(-)-sparteine followed by protonation of the resulting anion afforded (R)-phenyltetrahydroisoquinoline 1 in up to 88% e.e. Following the same procedure, racemic 2-(1-phenylethyl)pyridine 2 was subjected to the lithiation-protonation sequence. The stereochemical outcome of the sequence proved to be highly dependent on the proton sources giving either (S)- or (R)-2-(1-phenylethyl)pyridine 2 with EtOH or t-BuOH respectively in up to 50% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00228-6
• 作为产物：
  描述：

  4-苯基-1,2,3,4-四氢异喹啉盐酸盐 在 palladium dihydroxide 氘代甲醇-d 、 氢气 、 仲丁基锂 、 鹰爪豆碱 作用下， 反应 12.75h， 生成 (R)-N-methyl-4-(phenyldeuterio)-1,2,3,4-tetrahydroisoquinoline 1-d1
  参考文献：
  名称：

  Deracemization of diarylmethanes via lateral lithiation–protonation sequences by means of sparteine

  摘要：

  Deracemization of diarylmethane derivatives was investigated by lateral lithiation-protonation mediated by (-)sparteine. Treatment of racemic 4-phenyltetrahydroisoquinoline 1 with s-butyllithium-(-)-sparteine followed by protonation of the resulting anion afforded (R)-phenyltetrahydroisoquinoline 1 in up to 88% e.e. Following the same procedure, racemic 2-(1-phenylethyl)pyridine 2 was subjected to the lithiation-protonation sequence. The stereochemical outcome of the sequence proved to be highly dependent on the proton sources giving either (S)- or (R)-2-(1-phenylethyl)pyridine 2 with EtOH or t-BuOH respectively in up to 50% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00228-6