(2R,3S,11bS,Z)-methyl-5-benzylidene-2-methyl-2,3,5,11b-tetrahydrooxazolo[3',2':1,5]pyrrolo[3,4-b]quinoline-3-carboxylate | 1599446-39-5

• 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: (2R,3S,11bS,Z)-methyl-5-benzylidene-2-methyl-2,3,5,11b-tetrahydrooxazolo[3',2':1,5]pyrrolo[3,4-b]quinoline-3-carboxylate
• 英文别名: methyl (11S,13R,14S,16Z)-16-benzylidene-13-methyl-12-oxa-2,15-diazatetracyclo[8.6.0.03,8.011,15]hexadeca-1,3,5,7,9-pentaene-14-carboxylate
• CAS: 1599446-39-5
• 化学式: C₂₃H₂₀N₂O₃
• 分子量: 372.423
• InChiKey: ZEFABNWVXPEDFC-KPQWPOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-phenylethynyl-quinoline-3-carbaldehyde 、 L-苏氨酸甲酯盐酸盐 在 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 乙醇 为溶剂， 以70%的产率得到(2R,3S,11bS,Z)-methyl-5-benzylidene-2-methyl-2,3,5,11b-tetrahydrooxazolo[3',2':1,5]pyrrolo[3,4-b]quinoline-3-carboxylate
  参考文献：
  名称：

  Stereoselective tandem synthesis of oxazolo-fused pyrroloquinolines from o-alkynylaldehydes via Ag(I)-catalyzed regioselective 5-exo-dig ring closure

  摘要：

  A tandem approach for the regio- and stereoselective synthesis of oxazolo-fused pyrroloquinolines 3a-I via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The possible participation of the pyridine ring in the regioselective formation of 5-exo-dig cyclized products was supported by the controlled experiments. The structures and stereochemistry of the products were confirmed by NOESY and X-ray crystallographic studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.103