(E)-(R)-2-cyclohexyl(4-(2-quinolinylmethoxy)phenyl)methoxyiminopropionic acid | 177469-84-0

• 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: (E)-(R)-2-cyclohexyl(4-(2-quinolinylmethoxy)phenyl)methoxyiminopropionic acid
• 英文别名: (2E)-2-[(R)-cyclohexyl-[4-(quinolin-2-ylmethoxy)phenyl]methoxy]iminopropanoic acid
• CAS: 177469-84-0
• 化学式: C₂₆H₂₈N₂O₄
• 分子量: 432.519
• InChiKey: USBHSZPRMPADOE-MJHSOURCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-溴苄胺盐酸盐 、 (E)-(R)-2-cyclohexyl(4-(2-quinolinylmethoxy)phenyl)methoxyiminopropionic acid 在 N-羟基丁二酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以83%的产率得到(R)-2-E-[cyclohexyl-4-(2-quinolinylmethoxy)phenyl]methoxyiminopropionic acid N-(3-bromobenzyl)amide
  参考文献：
  名称：

  Synthesis and resolution of 2-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid, leukotriene biosynthesis inhibitors

  摘要：

  The synthesis and resolution of 2-(E)-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid 1, a potent leukotriene biosynthesis inhibitor is described. Dibenzoyltartaric acid was used as the chiral auxiliary for the resolution of the hydroxylamine intermediates used in the synthesis. A difficult chromatographic separation was made more practical by changing the order of elution of diastereomers by selection of the natural or unatural tartaric acid auxiliary. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00340-0
• 作为产物：
  描述：

  4-[(2-quinolinyl)-methoxy]-benzaldehyde 在 sodium hydroxide 、 一水合肼 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 38.5h， 生成 (E)-(R)-2-cyclohexyl(4-(2-quinolinylmethoxy)phenyl)methoxyiminopropionic acid
  参考文献：
  名称：

  Synthesis and resolution of 2-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid, leukotriene biosynthesis inhibitors

  摘要：

  The synthesis and resolution of 2-(E)-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid 1, a potent leukotriene biosynthesis inhibitor is described. Dibenzoyltartaric acid was used as the chiral auxiliary for the resolution of the hydroxylamine intermediates used in the synthesis. A difficult chromatographic separation was made more practical by changing the order of elution of diastereomers by selection of the natural or unatural tartaric acid auxiliary. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00340-0

文献信息

• Synthesis and resolution of 2-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid, leukotriene biosynthesis inhibitors
  作者：Teodozyj Kolasa、David E. Gunn、Andrew O. Stewart、Clint D.W. Brooks

  DOI：10.1016/0957-4166(96)00340-0

  日期：1996.9

  The synthesis and resolution of 2-(E)-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid 1, a potent leukotriene biosynthesis inhibitor is described. Dibenzoyltartaric acid was used as the chiral auxiliary for the resolution of the hydroxylamine intermediates used in the synthesis. A difficult chromatographic separation was made more practical by changing the order of elution of diastereomers by selection of the natural or unatural tartaric acid auxiliary. Copyright (C) 1996 Elsevier Science Ltd