4-[2-(tert-butyldiphenylsilyloxy)-1-methylethyl]quinoline | 220651-47-8

• 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: 4-[2-(tert-butyldiphenylsilyloxy)-1-methylethyl]quinoline
• 英文别名: Tert-butyl-diphenyl-(2-quinolin-4-ylpropoxy)silane
• CAS: 220651-47-8
• 化学式: C₂₈H₃₁NOSi
• 分子量: 425.646
• InChiKey: DFJBQXCPKPDTGW-UHFFFAOYSA-N

物化性质

• 沸点：
  516.9±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(tert-butyldiphenylsilyloxy)-1-methylethyl]quinoline 在 吡啶 、 氢氟酸 、 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 5.0h， 生成 4-[(RS)-2-acetoxy-1-methylethyl]-2-{(SR)-[(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：

  1-氯-3-戊酮 在 咪唑 、 盐酸 作用下， 以 水 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 4-[2-(tert-butyldiphenylsilyloxy)-1-methylethyl]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

• 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.