1-methyl-7-naphthyl-2-pyrrolino[3,2-c]pyridine | 219834-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-7-naphthyl-2-pyrrolino[3,2-c]pyridine
• 英文别名: 1-Methyl-7-(1-naphthyl)-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine；1-Methyl-7-naphthalen-1-yl-2,3-dihydropyrrolo[3,2-c]pyridine
• CAS: 219834-88-5
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: SAXAPEYTGKXNDV-UHFFFAOYSA-N

物化性质

• 沸点：
  455.7±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• 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

• 作为反应物：
  描述：

  1-methyl-7-naphthyl-2-pyrrolino[3,2-c]pyridine 、 碘甲烷 在 三氟化硼四氢呋喃络合物 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以71%的产率得到1,4-Dimethyl-7-(1-naphthyl)-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine boron trifluoride complex
  参考文献：
  名称：

  Atropisomeric α-methyl substituted analogues of 4-(dimethylamino)pyridine: synthesis and evaluation as acyl transfer catalysts

  摘要：

  4-(二甲基氨基)吡啶的 N-BF3 加合物的 α-金属化-甲基化的区域选择性作为 β-取代的函数进行了检查，试图制备具有 α-甲基的构型稳定的阻转异构衍生物（I 和 II）取代基和β-联芳立体异构轴。检查了其中一些衍生物作为酰基转移催化剂的活性，并报道了 α-甲基手性 DMAP (α)-24 催化的 1-(1-萘基)乙醇的动力学拆分。还提出了该催化剂相对于其非α-取代类似物(α)-1 立体选择性降低的基本原理。

  DOI：

  10.1039/b103385a
• 作为产物：
  描述：

  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 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.5h， 生成 1-methyl-7-naphthyl-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

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.