[(1S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-[2-hydroxy-1-(methoxymethoxy)propan-2-yl]phenyl]propyl] methanesulfonate | 186353-01-5

• 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: [(1S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-[2-hydroxy-1-(methoxymethoxy)propan-2-yl]phenyl]propyl] methanesulfonate
• CAS: 186353-01-5
• 化学式: C₃₂H₃₄ClNO₆S
• 分子量: 596.144
• InChiKey: GMHYYBRSFCKCDH-STYPEXNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-[2-hydroxy-1-(methoxymethoxy)propan-2-yl]phenyl]propyl] methanesulfonate 在 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 12.5h， 生成 methyl-(R,R/S)-1[((1-[3-(2-(7-chloro-2-quinolinyl)-(E)-ethenyl)phenyl]-3-(2-(1,2-dihydroxy-1-methylethyl)phenyl)propyl)thio)methyl]cyclopropane acetate
  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 正丁基锂 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 [(1S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-[2-hydroxy-1-(methoxymethoxy)propan-2-yl]phenyl]propyl] methanesulfonate
  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.