2'-nitrobenzylideneacetoacetic acid methyl ester | 70076-15-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2'-nitrobenzylideneacetoacetic acid methyl ester
• 英文别名: Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoate
• CAS: 70076-15-2
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: CJBFCOOECPQZDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-nitrobenzylideneacetoacetic acid methyl ester 、 乙酰乙酸正丙酯 在 氨 作用下， 以 乙醇 为溶剂， 以54%的产率得到2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-propyl ester
  参考文献：
  名称：

  Pharmaceutical compositions containing unsymmetrical esters of

  摘要：

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。

  公开号：

  US03932645A1
• 作为产物：
  描述：

  邻硝基苯甲醛 、 乙酰乙酸甲酯 、 哌啶乙酸盐 以to give methyl-2-nitro-benzylidene-acetoacetate with a high yield of about 97%的产率得到2'-nitrobenzylideneacetoacetic acid methyl ester
  参考文献：
  名称：

  Process for the preparation of 1,4-dihydro-pyridine derivatives

  摘要：

  本发明涉及一种制备二甲基-1,4-二氢-2,6-二甲基-4-(2'-硝基苯基)-吡啶-3,5-二羧酸二甲酯的方法，该方法通过将1-甲氧基-1-(2'-硝基苯基)-N-(2'-硝基苯基)亚甲基甲酰胺或1-(2'-硝基苯基)-N,N'-双-(2'-硝基苯基)亚甲基甲烷二胺与乙酰乙酸甲酯在胺化合物存在下反应，或通过将2-硝基苯甲醛亚胺的单体或三聚体与乙酰乙酸甲酯反应来实现。

  公开号：

  US05126457A1

文献信息

• 2-Amino-1,4-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03939171A1

  公开（公告）日：1976-02-17

  2-Amino-1,4-dihydropyridines bearing a carbonyl function in the 5-position and being optionally substituted by lower alkyl or phenyl in the 6-position, and the corresponding 2-amino-1,4,5,6,7,8-hexahydro-5-oxoquinolines, which derivatives are further substituted by a carbonyl group in the 3-position and optionally substituted 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-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and an amidine.

  5位带有羰基功能的2-氨基-1,4-二氢吡啶，6位可选择性地被低烷基或苯基取代，以及相应的2-氨基-1,4,5,6,7,8-六氢-5-氧喹啉衍生物，这些衍生物进一步在3位被羰基基团取代，在4位可选择性地被低烷基、苯基、取代苯基或杂环基团取代，它们是降压药和冠状血管扩张剂。这些化合物，其中2-氨基-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯是其代表性实施例，是通过酮酸酯和胺基甲酸盐的缩合制备而成。
• 2-Amino-4-pyrimidyl-1,4-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US04022898A1

  公开（公告）日：1977-05-10

  2-Amino-1,4-dihydropyridines bearing a carbonyl function in the 5-position and being optionally substituted by lower alkyl or phenyl in the 6-position, and the corresponding 2-amino-1,4,5,6,7,8-hexahydro-5-oxoquinolines, which derivatives are further substituted by a carbonyl group in the 3-position and optionally substituted 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-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and an amidine.

  在5位带有羰基功能并在6位可选择取代为较低烷基或苯基的2-氨基-1,4-二氢吡啶和相应的2-氨基-1,4,5,6,7,8-六氢-5-氧喹啉衍生物，其衍生物在3位进一步取代为羰基基团并在4位可选择取代为较低烷基、苯基、取代苯基或杂环基团，可作为降压剂和冠状血管扩张剂。这些化合物通过酰乙酰乙酸酯和肼的缩合反应制备，其中2-氨基-6-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯是一个代表性的实施例。
• 3-Aminocarbonyl-1,4-dihydropyridine-5-carboxylic acid compounds, and
  申请人：Nippon Shoji Kabushiki Kaisha

  公开号：US04874773A1

  公开（公告）日：1989-10-17

  Novel 3-aminocarbonyl-1,4-dihydropyridine-5-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3.5 alkynyl, C.sub.3-8 cycloalkyl, R.sup.2 is C.sub.1-10 alkyl, and the NO.sub.2 group is substituted at ortho- or meta-position, provided that when the NO.sub.2 group is substituted at ortho-position and R.sup.2 is methyl, R.sup.1 is C.sub.3-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, or C.sub.3-8 cycloalkyl, and when the NO.sub.2 group is substituted at meta-position and R.sup.1 is H, R.sup.2 is C.sub.3-10 alkyl, which have excellent hypotensive, vasodilating activities and are useful for the prophylaxis and treatment of hypertension, ischemic heart diseases and cerebral and peripheral circulation diseases.

  化合物的中文翻译如下：式中R1为氢、C1-5烷基、C2-5烯基、C3.5炔基、C3-8环烷基，R2为C1-10烷基，NO2基取代于邻位或间位，但当NO2基取代于邻位且R2为甲基时，R1为C3-5烷基、C2-5烯基、C3-5炔基或C3-8环烷基，当NO2基取代于间位且R1为氢时，R2为C3-10烷基。这些化合物具有出色的降压、扩血管活性，并可用于预防和治疗高血压、缺血性心脏病和脑外周循环疾病。
• Process for the preparation of 1,4-dihydro-pyridine derivatives
  申请人：Egis Gyogyszergyar

  公开号：US05126457A1

  公开（公告）日：1992-06-30

  The invention is directed to processes for the preparation of dimethyl-1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-pyridine-3,5-dicarbox ylate by reacting 1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylene methanamie or 1-(2'-nitrophenyl)-N,N'-bis-(2'-nitrophenyl) methylene methanediamine with methyl acetoacetate in the presence of an amine compound or by reacting the monomeric or trimeric from of 2-nitrobenzaldimine with methyl acetoacetate.

  本发明涉及一种制备二甲基-1,4-二氢-2,6-二甲基-4-(2'-硝基苯基)-吡啶-3,5-二羧酸二甲酯的方法，该方法通过将1-甲氧基-1-(2'-硝基苯基)-N-(2'-硝基苯基)亚甲基甲酰胺或1-(2'-硝基苯基)-N,N'-双-(2'-硝基苯基)亚甲基甲烷二胺与乙酰乙酸甲酯在胺化合物存在下反应，或通过将2-硝基苯甲醛亚胺的单体或三聚体与乙酰乙酸甲酯反应来实现。
• Pharmaceutical compositions containing unsymmetrical esters of
  申请人：Farbenfabriken Bayer AG

  公开号：US03932645A1

  公开（公告）日：1976-01-13

  Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility in the treatment of hypertension.

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。