2-[3-(benzyloxy)prop-1-ynyl]-4-(2-hydroxy-1-methylethyl)-2H-quinoline-1-carboxylic acid phenyl ester

• 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-[3-(benzyloxy)prop-1-ynyl]-4-(2-hydroxy-1-methylethyl)-2H-quinoline-1-carboxylic acid phenyl ester
• 英文别名: phenyl 4-(1-hydroxypropan-2-yl)-2-(3-phenylmethoxyprop-1-ynyl)-2H-quinoline-1-carboxylate
• 化学式: C₂₉H₂₇NO₄
• 分子量: 453.538
• InChiKey: NCJYCHFVSNVILT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-(benzyloxy)prop-1-ynyl]-4-(2-hydroxy-1-methylethyl)-2H-quinoline-1-carboxylic acid phenyl ester 在 三氟化硼乙醚 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 生成 4-[(RS)-2-hydroxy-1-methylethyl]-2-[(RS)-3-hydroxyprop-1-ynyl]-2H-quinoline-1-carboxylic acid phenyl ester 、 4-[(RS)-2-hydroxy-1-methylethyl]-2-[(SR)-3-hydroxyprop-1-ynyl]-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