N,N-dimethyl-3,3-diaminoacrylic acid ethyl ester | 52508-83-5

• 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: N,N-dimethyl-3,3-diaminoacrylic acid ethyl ester
• 英文别名: 3-Amino-3-dimethylaminoacrylic acid ethyl ester；ethyl 3-amino-3-(dimethylamino)prop-2-enoate
• CAS: 52508-83-5
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: LFEOOQXIDIXYBW-UHFFFAOYSA-N

物化性质

• 沸点：
  263.2±30.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  N,N-dimethyl-3,3-diaminoacrylic acid ethyl ester 在 2-(morpholin-4-yl)ethane-1-sulfonyl azide 、 三乙胺 作用下， 反应 1.0h， 以81%的产率得到ethyl 5-(dimethylamino)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  β-（环烷基氨基）乙烷磺酰叠氮化物作为合成重氮化合物和杂环的新型水溶性试剂

  摘要：

  合成了本质上是碱性的新型水溶性磺酰叠氮化物。所获得的化合物在重氮转移反应中用作重氮基团的供体。由于它们在水中的良好溶解性和高极性，在这种情况下形成的副产物很容易通过用水或柱色谱法洗涤而与所需产物分离。还显示出由于反应的结果，新的磺酰叠氮化物可以掺入杂环产物中，赋予它们水溶性。

  DOI：

  10.1007/s10593-019-02609-z
• 作为产物：
  描述：

  盐酸二甲胺 、 ethyl 3-amino-3-ethoxypropenoate 以 乙醇 为溶剂， 生成 N,N-dimethyl-3,3-diaminoacrylic acid ethyl ester
  参考文献：
  名称：

  Meyer,H. et al., Justus Liebigs Annalen der Chemie, 1977, p. 1895 - 1908

  摘要：

  DOI：

文献信息

• 2-Amino-6-dialkylaminodihydropyridines, their production, pharmaceutical
  申请人：Bayer Aktiengesellschaft

  公开号：US04004014A1

  公开（公告）日：1977-01-18

  2-Amino-6-dialkylaminodihydropyridines exist in tautomeric form and are represented by the formulae ##STR1## WHEREIN R.sub.1 and R.sub.3 are the same or different and each is straight, branched or cyclic alkyl, alkenyl or alkynyl or said alkyl, alkenyl or alkynyl interrupted by 1 or 2 oxygen atoms; R.sub.2 is a saturated, partially unsaturated or unsaturated straight, branched or cyclic hydrocarbon; aryl unsubstituted or substituted by 1, 2 or 3 of the same or different substituents selected from the group consisting of alkyl, alkoxy, azido, halo, cyano, nitro, trifluoromethyl, carbalkoxy and SO.sub.n -alkyl wherein n is 0, 1 or 2; naphthyl; quinolyl; isoquinolyl; pyridyl; pyrimidyl; thenyl; or furyl; and R.sub.4 and R.sub.5 are each lower alkyl; benzyl; or, together with the nitrogen atom to which they are attached, a 4- to 7-membered ring. These compounds are useful for their coronary-vessel-dilating effect, their antihypertensive effect, their anti-fibrillation effect, their vascular-spasmolytic effect and their muscular-spasmolytic effect.

  2-氨基-6-二烷基氨基二氢吡啶存在互变异构体，并由以下式子表示：##STR1## 其中R.sub.1和R.sub.3相同或不同，每个都是直链，支链或环烷基，烯基或炔基，或者是由1或2个氧原子中断的所述烷基，烯基或炔基；R.sub.2是饱和的，部分不饱和的或不饱和的直链，支链或环烃基；芳基未取代或取代1,2或3个相同或不同的取代基，所述取代基选自由烷基，烷氧基，叠氮基，卤素，氰基，硝基，三氟甲基，羧烷氧基和SO.sub.n-烷基，其中n为0,1或2；萘基；喹啉基；异喹啉基；吡啶基；嘧啶基；蒽基；或呋喃基；R.sub.4和R.sub.5各自是较低的烷基；苄基；或与它们连接的氮原子一起形成4-到7元环。这些化合物对于其扩张冠状血管作用、其降压作用、其抗心房颤动作用、其血管痉挛作用和其肌肉痉挛作用是有用的。
• 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.