3-(2-Hydroxyethylamino)-but-2-enoic acid methyl ester | 154051-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(2-Hydroxyethylamino)-but-2-enoic acid methyl ester
• 英文别名: methyl 3-(2-hydroxyethylamino)but-2-enoate
• CAS: 154051-78-2
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: HQNHEEOUOOANLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Hydroxyethylamino)-but-2-enoic acid methyl ester 、 2-(3-硝基苯亚甲基)乙酰乙酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl 7-(3-nitrophenyl)-5,8a-dimethyl-8-methoxycarbonyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-carboxylate
  参考文献：
  名称：

  Oxazolo[3,2-a]pyridine. A new structural scaffold for the reversal of multi-drug resistance in Leishmania

  摘要：

  Compounds belonging to three different classes of fused heterocyclic systems, structurally related to Calcium-channel blockers of the 1,4-dihydropyridine family, were evaluated in their ability to overcome leishmanial resistance to common drugs in a MDR Leishmania tropica strain. Compounds with the skeletal basis of oxazolo[3,2-a]pyridine displayed significant reversion of resistance to daunomycin and miltefosine, with reversion indexes up to 6.7-fold and 8.7-fold, respectively. Most interestingly, the enantiopure compound 20S attained to revert the resistance to both drugs and fairly more significantly than its enantiomer 20R. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.100
• 作为产物：
  描述：

  C.I.酸性橙108 、 乙酰乙酸甲酯 在 indium(III) chloride 作用下， 反应 0.5h， 生成 3-(2-Hydroxyethylamino)-but-2-enoic acid methyl ester
  参考文献：
  名称：

  对2-吡咯啉-5-酮的三组分访问及其在面向靶标和面向多样性的合成中的使用

  摘要：

  在三氯化铟存在下，伯胺，小β-二羰基化合物和小α-溴代酸酯之间的Hantzsch型微波辅助无溶剂顺序三组分反应可得到2-吡咯啉-5-酮。很难通过其他方法来访问...。

  DOI：

  10.1039/c6ra06317a

文献信息

• 1,4-dihydropyridines, N-substituted bicyclic 4-hydropyridines, and
  申请人：Apotex, Inc.

  公开号：US05723618A1

  公开（公告）日：1998-03-03

  The invention relates to a novel process to prepare 1,4-dihydropyridines and in particular amlopidine and in novel intermediates obtained during the synthesis of the 1,4-dihydropyridines which have potential activity as antihypertensive agents.

  本发明涉及一种制备1,4-二氢吡啶的新工艺，特别是氨氯地平，并涉及在1,4-二氢吡啶的合成过程中获得的新中间体，这些中间体具有作为降压药物的潜在活性。
• Three-component access to 2-pyrrolin-5-ones and their use in target-oriented and diversity-oriented synthesis
  作者：Ángel Cores、Verónica Estévez、Mercedes Villacampa、J. Carlos Menéndez

  DOI：10.1039/c6ra06317a

  日期：——

  The Hantzsch-type microwave-assisted, solvent-free sequential three-component reaction between primary amines, [small beta]-dicarbonyl compounds and [small alpha]-bromoesters in the presence of indium trichloride afforded 2-pyrrolin-5-ones, which are difficult to access by alternative methods....

  在三氯化铟存在下，伯胺，小β-二羰基化合物和小α-溴代酸酯之间的Hantzsch型微波辅助无溶剂顺序三组分反应可得到2-吡咯啉-5-酮。很难通过其他方法来访问...。
• Oxazolo[3,2-a]pyridine. A new structural scaffold for the reversal of multi-drug resistance in Leishmania
  作者：Esther Caballero、José Ignacio Manzano、Pilar Puebla、Santiago Castanys、Francisco Gamarro、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2012.07.100

  日期：2012.10

  Compounds belonging to three different classes of fused heterocyclic systems, structurally related to Calcium-channel blockers of the 1,4-dihydropyridine family, were evaluated in their ability to overcome leishmanial resistance to common drugs in a MDR Leishmania tropica strain. Compounds with the skeletal basis of oxazolo[3,2-a]pyridine displayed significant reversion of resistance to daunomycin and miltefosine, with reversion indexes up to 6.7-fold and 8.7-fold, respectively. Most interestingly, the enantiopure compound 20S attained to revert the resistance to both drugs and fairly more significantly than its enantiomer 20R. (C) 2012 Elsevier Ltd. All rights reserved.