(S)-4-{1-[(triethylsilyloxy)methyl]-2-(trityloxy)ethyl}quinoline | 526203-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-4-{1-[(triethylsilyloxy)methyl]-2-(trityloxy)ethyl}quinoline
• 英文别名: triethyl-[(2S)-2-quinolin-4-yl-3-trityloxypropoxy]silane
• CAS: 526203-41-8
• 化学式: C₃₇H₄₁NO₂Si
• 分子量: 559.824
• InChiKey: ZZABSIPAVZQXDO-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.35
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲酸苯酯 、 三甲基乙炔基硅 、 (S)-4-{1-[(triethylsilyloxy)methyl]-2-(trityloxy)ethyl}quinoline 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 4-[(S)-1-(triethylsilyloxy)methyl-2-(trityloxy)ethyl]-2-{(R)-[(trimethylsilyl)ethynyl]}-2H-quinoline-1-carboxylic acid phenyl ester 、 4-[(S)-1-(triethylsilyloxy)methyl-2-(trityloxy)ethyl]-2-{(S)-[(trimethylsilyl)ethynyl]}-2H-quinoline-1-carboxylic acid phenyl ester
  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
• 作为产物：
  描述：

  [(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate 在 吡啶 、 2,6-二甲基吡啶 、 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-4-{1-[(triethylsilyloxy)methyl]-2-(trityloxy)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.