2-[(S)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile | 1215476-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(S)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile
• 英文别名: (2S)-2-(2-chloroquinolin-3-yl)-2-[[(1R)-1-(4-methoxyphenyl)ethyl]amino]acetonitrile
• CAS: 1215476-61-1
• 化学式: C₂₀H₁₈ClN₃O
• 分子量: 351.835
• InChiKey: KWSJQCQMAJIDEP-BFUOFWGJSA-N

物化性质

• 沸点：
  533.1±50.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(S)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以93%的产率得到2-氯喹啉-3-甲酸
  参考文献：
  名称：

  Efficient synthesis and X-ray structures of new α-quinolin-3-yl-α-aminonitriles and derivatives

  摘要：

  This study describes the synthesis of novel alpha-aminonitrile derivatives possessing a quinoline subunit via a Strecker reaction. Chiral alpha-methylbenzylamines were used to carry out the diastereoselective version of this sequence. Conversion of an enantiopure 2-chloroquinolin-3-yl derivative into the corresponding alpha-aminoester resulted in the concomitant formation of a 2(1H)-quinolinone moiety and a partial racemization. Single crystal X-ray structures are reported for three compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.032
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 、 (R)-(+)-1-(4-甲氧基苯)乙胺 以 甲醇 、 乙腈 为溶剂， 生成 2-[(S)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile 、 2-[(R)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile
  参考文献：
  名称：

  Efficient synthesis and X-ray structures of new α-quinolin-3-yl-α-aminonitriles and derivatives

  摘要：

  This study describes the synthesis of novel alpha-aminonitrile derivatives possessing a quinoline subunit via a Strecker reaction. Chiral alpha-methylbenzylamines were used to carry out the diastereoselective version of this sequence. Conversion of an enantiopure 2-chloroquinolin-3-yl derivative into the corresponding alpha-aminoester resulted in the concomitant formation of a 2(1H)-quinolinone moiety and a partial racemization. Single crystal X-ray structures are reported for three compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.032

文献信息

• Efficient synthesis and X-ray structures of new α-quinolin-3-yl-α-aminonitriles and derivatives
  作者：Souheila Ladraa、Fabienne Berrée、Abdelmalek Bouraiou、Sofiane Bouacida、Thierry Roisnel、Bertrand Carboni、Ali Belfaitah

  DOI：10.1016/j.tetlet.2012.11.032

  日期：2013.2

  This study describes the synthesis of novel alpha-aminonitrile derivatives possessing a quinoline subunit via a Strecker reaction. Chiral alpha-methylbenzylamines were used to carry out the diastereoselective version of this sequence. Conversion of an enantiopure 2-chloroquinolin-3-yl derivative into the corresponding alpha-aminoester resulted in the concomitant formation of a 2(1H)-quinolinone moiety and a partial racemization. Single crystal X-ray structures are reported for three compounds. (C) 2012 Elsevier Ltd. All rights reserved.