4-[1-methyl-2-(p-nitrophenoxy)ethyl]quinoline | 220651-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[1-methyl-2-(p-nitrophenoxy)ethyl]quinoline
• 英文别名: 4-[1-(4-Nitrophenoxy)propan-2-yl]quinoline；4-[1-(4-nitrophenoxy)propan-2-yl]quinoline
• CAS: 220651-51-4
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: RNWPHAHUTVMVDG-UHFFFAOYSA-N

物化性质

• 沸点：
  499.9±30.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  magnesium,ethynyl(trimethyl)silane,bromide 、 氯甲酸苯酯 、 4-[1-methyl-2-(p-nitrophenoxy)ethyl]quinoline 以 四氢呋喃 为溶剂， 生成 4-[(RS)-1-methyl-2-(p-nitrophenoxy)ethyl]-2-{(RS)-[(trimethylsilyl)ethynyl]}-2H-quinoline-1-carboxylic acid phenyl ester 、 4-[(RS)-1-methyl-2-(p-nitrophenoxy)ethyl]-2-{(SR)-[(trimethylsilyl)ethynyl]}-2H-quinoline-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol

  摘要：

  Differently O-protected 2-(4-quinolyl)propanols undergo, in the presence of chloroformate esters, a regio- and stereoselective addition of acetylides on the carbon alpha to nitrogen with moderate to good diastereoselectivity. The bulkiness of the OH protecting group, which has a 1,7 relationship with the newly created stereocentre, appears to be mainly responsible for this remote stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00418-2
• 作为产物：
  描述：

  4-乙基喹啉 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 59.5h， 生成 4-[1-methyl-2-(p-nitrophenoxy)ethyl]quinoline
  参考文献：
  名称：

  O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines

  摘要：

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00711-5

文献信息

• O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines
  作者：Giuseppe Guanti、Sara Perrozzi、Renata Riva

  DOI：10.1016/s0957-4166(02)00711-5

  日期：2002.12

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol
  作者：Giuseppe Guanti、Sara Perrozzi、Renata Riva

  DOI：10.1016/s0957-4166(98)00418-2

  日期：1998.11

  Differently O-protected 2-(4-quinolyl)propanols undergo, in the presence of chloroformate esters, a regio- and stereoselective addition of acetylides on the carbon alpha to nitrogen with moderate to good diastereoselectivity. The bulkiness of the OH protecting group, which has a 1,7 relationship with the newly created stereocentre, appears to be mainly responsible for this remote stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.