3-Amino-3-(1-pyrrolidinyl)acrylsaeure-ethylester | 52508-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-Amino-3-(1-pyrrolidinyl)acrylsaeure-ethylester
• 英文别名: ethyl 3-amino-3-(pyrrolidin-1-yl)acrylate；3-Pyrrolidino-3-aminoacrylic acid ethyl ester；ethyl 3-amino-3-pyrrolidin-1-ylprop-2-enoate
• CAS: 52508-81-3
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: IBVJGPALPZCISO-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  321.1±35.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Amino-3-(1-pyrrolidinyl)acrylsaeure-ethylester 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 4,5-Dihydro-5-imino-4-(methoxycarbonylimino)-2-(1-pyrrolidinyl)-1H-pyrrol-3-carbonsaeure-ethylester
  参考文献：
  名称：

  Kinast, Guenther, Liebigs Annalen der Chemie, 1981, # 9, p. 1561 - 1567

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙氧基-3-亚氨基丙酸乙酯盐酸盐 在 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 3-Amino-3-(1-pyrrolidinyl)acrylsaeure-ethylester
  参考文献：
  名称：

  由π缺陷的1,2-二卤代芳烃和双烯键烯胺合成2-氨基吲哚和6-氨基吡咯并[3,2-d]嘧啶的新方法

  摘要：

  摘要 提出了一种通过双烯二胺和π-缺陷的1,2-二卤代芳烃合成稠合的2-氨基吡咯的有效方法。两步法包括用二烯二胺C-亲核中心芳族亲核取代二卤代芳烃的活化卤素，然后进行Cu催化的分子内N-芳基化。该方法允许在温和条件下以中等和良好收率获得各种2-氨基-6-硝基吲哚和6-氨基吡咯并[3,2- d ]嘧啶（包括N-单-和N，N-二取代）。 提出了一种通过双烯二胺和π-缺陷的1,2-二卤代芳烃合成稠合的2-氨基吡咯的有效方法。两步法包括用二烯二胺C-亲核中心芳族亲核取代二卤代芳烃的活化卤素，然后进行Cu催化的分子内N-芳基化。该方法允许在温和条件下以中等和良好收率获得各种2-氨基-6-硝基吲哚和6-氨基吡咯并[3,2- d ]嘧啶（包括N-单-和N，N-二取代）。

  DOI：

  10.1055/s-0035-1561645

文献信息

• 2-Amino-4,5-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03959292A1

  公开（公告）日：1976-05-25

  4,5-Dihydropyridines bearing an N,N-disubstituted amino group in the 2-position, carbonyl functions in the 3- and 5-positions and being optionally substituted in the 6-position by lower alkyl or phenyl and, in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, are antihypertensive agents and coronary vessel dilators. The compounds, of which 2-pyrrolidino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxy lic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a substituted 3,3-diaminoacrylate.

  2-位带有 N,N-二取代氨基基团，3-位和5-位带有羰基功能团的4,5-二氢吡啶，可选择性地在6-位被低碳烷基或苯基取代，在4-位被低碳烷基、苯基、取代苯基或杂环基取代。这些化合物是降压药和冠状血管扩张剂。其中2-吡咯烷基-6-甲基-4-(3-硝基苯基)-4,5-二氢吡啶-3,5-二羧酸3,5-二乙酯是一种代表性的化合物，通过酰乙酸乙酯和取代的3,3-二氨基丙烯酸酯的缩合反应制备。
• Antihypertensive 2-amino-4,5-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US04136187A1

  公开（公告）日：1979-01-23

  4,5-Dihydropyridines bearing an N,N-disubstituted amino group in the 2-position, carbonyl functions in the 3- and 5-positions and being optionally substituted in the 6-position by lower alkyl or phenyl and, in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, are antihypertensive agents and coronary vessel dilators. The compounds, of which 2-pyrrolidino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxy lic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a substituted 3,3-diaminoacrylate.

  在2位带有N,N-二取代氨基的4,5-二氢吡啶中，3位和5位带有羰基功能基团，6位可选择地被低碳基或苯基取代，在4位被低碳基、苯基、取代苯基或杂环基团取代，这些化合物是降压剂和冠状血管扩张剂。这些化合物通过酰乙酸酯和取代的3,3-二氨基丙烯酸酯的缩合反应制备，其中2-吡咯烷基-6-甲基-4-(3-硝基苯基)-4,5-二氢吡啶-3,5-二羧酸3,5-二乙酯是一个典型的实施例。
• Design and Synthesis of Novel 2-Amino-5-hydroxyindole Derivatives That Inhibit Human 5-Lipoxygenase
  作者：Jens Landwehr、Sven George、Eva-Maria Karg、Daniel Poeckel、Dieter Steinhilber、Reinhard Troschuetz、Oliver Werz

  DOI：10.1021/jm050801i

  日期：2006.7.1

  Compounds that inhibit 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of leukotrienes (LTs), possess potential for the treatment of inflammatory and allergic diseases as well as of atherosclerosis and cancer. Here we present the design and the synthesis of a series of novel 2-amino-5-hydroxyindoles that potently inhibit isolated human recombinant 5-LO as well as 5-LO in polymorphonuclear leukocytes, exemplified by ethyl 2-[(3-chlorophenyl)amino]-5-hydroxy-1H-indole-3-carboxylate (3n, IC50 value congruent to 300 nM). Introduction of an aryl/arylethylamino group or 4-arylpiperazin-1-yl residues into position 2 of the 5-hydroxyindoles was essential for biological activity. Whereas the 4-arylpiperazin-1-yl derivatives were more potent in cell-free assays as compared to intact cell test systems, aryl/arylethylamino derivatives inhibited 5-LO activity in intact cells and cell-free assays almost equally well. On the basis of their 5-LO inhibitory properties, these novel 2-amino-5-hydroxyindoles represent potential candidates for the pharmacological intervention with LT-associated diseases.