[2-((2R,4S,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone | 184763-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-((2R,4S,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone
• 英文别名: [2-[(2R,4S,6S)-6-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-2-phenyl-1,3-dioxan-4-yl]phenyl]-piperidin-1-ylmethanone
• CAS: 184763-93-7
• 化学式: C₃₉H₃₅ClN₂O₃
• 分子量: 615.172
• InChiKey: KTYXFHUYPHCXQX-OYBOEISFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-((2R,4S,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以83%的产率得到(3S)-3-[(2S)-2-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-2-hydroxyethyl]-3H-2-benzofuran-1-one
  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：

  3-(2-{3-[2-(7-chloro-2-quinolinyl)-(E)-ethenyl]phenyl}-(S)-2-hydroxyethyl)-(R/S)-3H-isobenzofuran-1-one 在 甲基氯化镁 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 [2-((2R,4S,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone
  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