2-methoxy-1-(1-methyl(2-pyrrolino[2,3-d]pyridin-7-yl))naphthalene | 219834-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-1-(1-methyl(2-pyrrolino[2,3-d]pyridin-7-yl))naphthalene
• 英文别名: 7-(2-Methoxynaphthalen-1-yl)-1-methyl-2,3-dihydropyrrolo[3,2-c]pyridine
• CAS: 219834-89-6
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: KCNPKPMESDOOKC-UHFFFAOYSA-N

物化性质

• 沸点：
  454.422±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.179±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-(1-methyl(2-pyrrolino[2,3-d]pyridin-7-yl))naphthalene 在 吡啶 、 三氯化铝 、 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 乙硫醇 作用下， 以 乙醚 为溶剂， 反应 25.17h， 生成 (+/-)-1-methyl-7-(2-phenylnaphthyl)-2-pyrrolino[3,2-c]pyridine
  参考文献：
  名称：

  Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine:  A Novel Class of Chiral Nucleophilic Catalysts

  摘要：

  A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an Ar-Ar bond, has been developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core 16 by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls 31, 38, and 43 containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, respectively, have demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing Ar-Ar rotation. Biaryls containing all three cores have been shown to retain DMAP-like catalytic activity in the acylation of a hindered alcohol. Biaryls 55 and 56, which are configurationally stable at ambient temperature, have also been prepared via modification of configurationally labile derivatives. Compounds 55 and 56 in optically pure form should provide a useful starting point for studies on catalytic asymmetric acyl transfer using atropisomeric analogues of DMAP.

  DOI：

  10.1021/jo991011h
• 作为产物：
  描述：

  1-甲基-2,3-二氢-1H-吡咯并[3,2-c]吡啶 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 2-methoxy-1-(1-methyl(2-pyrrolino[2,3-d]pyridin-7-yl))naphthalene
  参考文献：
  名称：

  Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine:  A Novel Class of Chiral Nucleophilic Catalysts

  摘要：

  A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an Ar-Ar bond, has been developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core 16 by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls 31, 38, and 43 containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, respectively, have demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing Ar-Ar rotation. Biaryls containing all three cores have been shown to retain DMAP-like catalytic activity in the acylation of a hindered alcohol. Biaryls 55 and 56, which are configurationally stable at ambient temperature, have also been prepared via modification of configurationally labile derivatives. Compounds 55 and 56 in optically pure form should provide a useful starting point for studies on catalytic asymmetric acyl transfer using atropisomeric analogues of DMAP.

  DOI：

  10.1021/jo991011h

文献信息

• Synthesis of atropisomeric analogues of DMAP
  作者：Alan C. Spivey、Tomasz Fekner、Harry Adams

  DOI：10.1016/s0040-4039(98)01951-0

  日期：1998.11

  A method for the preparation of 7-aryl derivatives of N-methyl-5-azaindoline involving Suzuki cross-coupling is described. Certain biaryls prepared in this manner exhibit atropisomerism. in particular, azaindoline 11 is shown to be configurationally stable at room temperature and to catalyse efficiently the esterification of 1-methylcyclohexanol with Ac2O. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine:  A Novel Class of Chiral Nucleophilic Catalysts
  作者：Alan C. Spivey、Tomasz Fekner、Sharon E. Spey、Harry Adams

  DOI：10.1021/jo991011h

  日期：1999.12.1

  A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an Ar-Ar bond, has been developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core 16 by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls 31, 38, and 43 containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, respectively, have demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing Ar-Ar rotation. Biaryls containing all three cores have been shown to retain DMAP-like catalytic activity in the acylation of a hindered alcohol. Biaryls 55 and 56, which are configurationally stable at ambient temperature, have also been prepared via modification of configurationally labile derivatives. Compounds 55 and 56 in optically pure form should provide a useful starting point for studies on catalytic asymmetric acyl transfer using atropisomeric analogues of DMAP.