(4R)-5-ethoxycarbonyl-4,6-dimethyl-1-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenylpropionyl]-3,4-dihydropyrimidin-2(1H)-one | 1388627-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (4R)-5-ethoxycarbonyl-4,6-dimethyl-1-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenylpropionyl]-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl (6R)-3-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]-4,6-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• CAS: 1388627-80-2
• 化学式: C₂₆H₂₅N₃O₆
• 分子量: 475.501
• InChiKey: XMGIJZHHDSMWAF-QRWLVFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-5-ethoxycarbonyl-4,6-dimethyl-1-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenylpropionyl]-3,4-dihydropyrimidin-2(1H)-one 在 lithium aluminium tetrahydride 、 水 、 rochelle salt 作用下， 以 四氢呋喃 为溶剂， 生成 (4S)-ethyl 1,2,3,4-tetrahydro-4,6-dimethyl-2-oxopyrimidine-5-carboxylate 、 (4R)-ethyl 1,2,3,4-tetrahydro-4,6-dimethyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  Chemical resolution of enantiomers of 3,4-dihydropyrimidin-2(1H)-ones using chiral auxiliary approach

  摘要：

  Inherently racemic DHPMs have been resolved using chemical resolution methodology by appending enantiopure chiral auxiliary at N-1 or N-3 position of the DHPMs, leading to the formation of both diastereomers, which were separated chromatographically to obtain both enantiomers (ee upto 99.9%) of DHPMs, after removal of the auxiliary. Absolute configuration of the enantiomers has been assigned. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.073
• 作为产物：
  描述：

  ethyl 4,6-dimethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 phthaloyl-L-phenylalanyl chloride 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以30%的产率得到(4S)-5-ethoxycarbonyl-4,6-dimethyl-1-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenylpropionyl]-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Chemical resolution of enantiomers of 3,4-dihydropyrimidin-2(1H)-ones using chiral auxiliary approach

  摘要：

  Inherently racemic DHPMs have been resolved using chemical resolution methodology by appending enantiopure chiral auxiliary at N-1 or N-3 position of the DHPMs, leading to the formation of both diastereomers, which were separated chromatographically to obtain both enantiomers (ee upto 99.9%) of DHPMs, after removal of the auxiliary. Absolute configuration of the enantiomers has been assigned. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.073