methyl N-benzyl-N-(3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)valinate | 597558-91-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N-benzyl-N-(3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)valinate
• 英文别名: methyl (2S)-2-[benzyl-(3-formyl-4-oxopyrido[1,2-a]pyrimidin-2-yl)amino]-3-methylbutanoate
• CAS: 597558-91-3
• 化学式: C₂₂H₂₃N₃O₄
• 分子量: 393.442
• InChiKey: KXJQZTHFXFXTML-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 methyl N-benzyl-N-(3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)valinate 以 甲苯 为溶剂， 反应 7.0h， 以68%的产率得到methyl 1-benzyl-2-isopropyl-3-[1-(1-naphthyl)ethyl]amino-4-oxo-1,2,3,4-tetrahydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidine-2-carboxylate
  参考文献：
  名称：

  Stereoselective pyrroline-ring formation through the cyclization of conjugated azomethine ylides at the periphery of pyrido[1,2-a]pyrimidine system

  摘要：

  The thermal reaction of N-benzyl-N-[3-(N-substituted imino)methyl-4-oxo-4H-pyrido[1,2-a] pyrimidin-2-yl] amino acid esters, generated from aldehyde esters and primary amines, provides 2,3-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidin-4(1H)-one derivatives effectively and stereoselectively. Therein, the stereoselective generation of conjugated azomethine ylides from the imine esters and their cyclization is essential for the pyrroline-ring formation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00657-4
• 作为产物：
  描述：

  N-苄基-L-缬氨酸甲酯 、 2-氯-4-氧代-4H-吡啶并[1,2-a]嘧啶-3-甲醛 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以62%的产率得到methyl N-benzyl-N-(3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)valinate
  参考文献：
  名称：

  Stereoselective pyrroline-ring formation through the cyclization of conjugated azomethine ylides at the periphery of pyrido[1,2-a]pyrimidine system

  摘要：

  The thermal reaction of N-benzyl-N-[3-(N-substituted imino)methyl-4-oxo-4H-pyrido[1,2-a] pyrimidin-2-yl] amino acid esters, generated from aldehyde esters and primary amines, provides 2,3-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidin-4(1H)-one derivatives effectively and stereoselectively. Therein, the stereoselective generation of conjugated azomethine ylides from the imine esters and their cyclization is essential for the pyrroline-ring formation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00657-4

文献信息

• Stereoselective pyrroline-ring formation through the cyclization of conjugated azomethine ylides at the periphery of pyrido[1,2-a]pyrimidine system
  作者：Michihiko Noguchi、Masashi Shirai、Kuniko Nakashima、Ichiro Arai、Akiko Nishida、Hidetoshi Yamamoto、Akikazu Kakehi

  DOI：10.1016/s0040-4020(03)00657-4

  日期：2003.6

  The thermal reaction of N-benzyl-N-[3-(N-substituted imino)methyl-4-oxo-4H-pyrido[1,2-a] pyrimidin-2-yl] amino acid esters, generated from aldehyde esters and primary amines, provides 2,3-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidin-4(1H)-one derivatives effectively and stereoselectively. Therein, the stereoselective generation of conjugated azomethine ylides from the imine esters and their cyclization is essential for the pyrroline-ring formation. (C) 2003 Elsevier Science Ltd. All rights reserved.