2-[(3S)-1-bromo-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoic acid | 1026009-57-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-[(3S)-1-bromo-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoic acid
• CAS: 1026009-57-3
• 化学式: C₂₇H₂₁BrClNO₃
• 分子量: 522.826
• InChiKey: IESNLBCKHPVUAE-VKBYXSOVSA-N

物化性质

• 沸点：
  683.5±55.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(3S)-1-bromo-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoic acid 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-2-[(1S)-3-oxo-1H-2-benzofuran-1-yl]ethyl] butane-1-sulfonate
  参考文献：
  名称：

  Synthesis of Montelukast (MK-0476) Metabolic Oxidation Products

  摘要：

  We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.

  DOI：

  10.1021/jo9615817
• 作为产物：
  描述：

  [S-(E)]-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 27.25h， 生成 2-[(3S)-1-bromo-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoic acid
  参考文献：
  名称：

  Synthesis of Montelukast (MK-0476) Metabolic Oxidation Products

  摘要：

  We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.

  DOI：

  10.1021/jo9615817

文献信息

• Synthesis of Montelukast (MK-0476) Metabolic Oxidation Products
  作者：Claude Dufresne、Michel Gallant、Yves Gareau、Réjean Ruel、Laird Trimble、Marc Labelle

  DOI：10.1021/jo9615817

  日期：1996.1.1

  We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.