(-)-7-{2-[3,5-bis(3,5-dimethylphenyl)phenyl]napthyl}-1-methyl-2-pyrrolidino[3,2-c]pyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-7-{2-[3,5-bis(3,5-dimethylphenyl)phenyl]napthyl}-1-methyl-2-pyrrolidino[3,2-c]pyridine
• 英文别名: 7-[2-[3,5-Bis(3,5-dimethylphenyl)phenyl]naphthalen-1-yl]-1-methyl-2,3-dihydropyrrolo[3,2-c]pyridine
• 化学式: C₄₀H₃₆N₂
• 分子量: 544.739
• InChiKey: IRTCLJCNTYEMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲基溴苯 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) CSP HPLC 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 15.67h， 生成 (-)-7-{2-[3,5-bis(3,5-dimethylphenyl)phenyl]napthyl}-1-methyl-2-pyrrolidino[3,2-c]pyridine
  参考文献：
  名称：

  Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations

  摘要：

  A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).

  DOI：

  10.1021/jo0000574

文献信息

• Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations
  作者：Alan C. Spivey、Tomasz Fekner、Sharon E. Spey

  DOI：10.1021/jo0000574

  日期：2000.5.1

  A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).