2-chloromethyl-3,5-dicarboethoxy-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine | 105435-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloromethyl-3,5-dicarboethoxy-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine
• 英文别名: 2-chloromethyl-3,5-dicarboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine；diethyl 2-(chloromethyl)-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate；2-chloromethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine；diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 105435-14-1
• 化学式: C₁₉H₂₁ClN₂O₆
• 分子量: 408.839
• InChiKey: BQZUKPLXYKHMHX-UHFFFAOYSA-N

物化性质

• 熔点：
  117-120 °C
• 沸点：
  524.1±50.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-3,5-dicarboethoxy-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine 在 potassium iodide 作用下， 以 丙酮 为溶剂， 生成 2-iodomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine
  参考文献：
  名称：

  1,4-dihydropyridines

  摘要：

  式I的二氢吡啶类化合物，其中R是氢或较低烷基；R1是CN、NO2、COCH3、COPh基团、羧基烷氧基或羧酰胺基团；R2是芳香或杂环芳基，单环或双环，最终被取代的苯基基团；R3是羧基烷氧基；A是卤素原子或铵或膦残基。这些化合物I可用作抗高血压、抗肿瘤、抗转移、抗血栓和/或抗缺血剂。

  公开号：

  US04839348A1
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 氨 作用下， 反应 2.67h， 生成 2-chloromethyl-3,5-dicarboethoxy-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  Zhang, Jian; Jin, Long Fei, Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 6, p. 916 - 921

  摘要：

  DOI：

文献信息

• 2-thiomethyl-substituted-1,4-dihydropyridines, method for their
  申请人：Boehringer Biochemia Robin S.p.A.

  公开号：US04999362A1

  公开（公告）日：1991-03-12

  Compounds of formula I ##STR1## wherein R.sub.1 is an alkoxycarbonyl group, acetyl, benzoyl, cyano, nitro or aminocarbonyl; R.sub.2 is an optionally substituted aryl or hetaryl group; R.sub.3 is an alkoxycarbonyl group; .phi. is a thio residue such as alkylthio, cycloalkylthio, arylthio, heteroarylthio, aminoalkylthio, are described. Compounds I are useful in human therapy as antihypertensive, antiulcer, antithrombotic, antiischaemic agents.

  式I的化合物##STR1##其中R.sub.1是烷氧羰基、乙酰基、苯甲酰基、氰基、硝基或氨基羰基；R.sub.2是可选择取代的芳基或杂环基；R.sub.3是烷氧羰基；.phi.是硫残基，如烷基硫、环烷基硫、芳基硫、杂环芳基硫、氨基烷基硫。化合物I在人类治疗中作为降压、抗溃疡、抗血栓、抗缺血剂方面具有用处。
• Studies on Nilvadipine. I. Synthesis and Structure-Activity Relationships of 1,4-Dihydropyridines Containing Novel Substituents at the 2-Position.
  作者：Yoshinari SATOH、Masaharu ICHIHASHI、Kazuo OKUMURA

  DOI：10.1248/cpb.39.3189

  日期：——

  The synthesis of new 1,4-dihydropyridine derivatives containing novel substituent at the 2-position of the nucleus via the key intermediate 2-formyl-1,4-dihydropyridines (X), is described. The aldehydes (X) were prepared by hydrolysis of the acetals (IX) which were obtained from aryl aldehyde (V) and alkyl 4,4-dialkoxyacetoacetate (VI) by the Knoevenagel reaction and treatment with alkyl 3-aminocrotonate

  描述了通过关键中间体2-甲酰基-1,4-二氢吡啶（X）合成在核的2-位含有新取代基的新的1,4-二氢吡啶衍生物。醛（X）的制备是通过Knoevenagel反应水解由芳基醛（V）和4,4-二烷氧基乙酰乙酸烷基酯（VI）得到的缩醛（IX）并按照3-氨基巴豆酸烷基酯（VIII）处理改进的Hantzsch方法。醛（X）的甲酰基具有足够的反应性，可以转化为各种官能团，例如羟甲基，氰基，取代的亚氨基甲基，氨基甲酰基，半氨基甲酸酯，取代的乙烯基，乙炔基等。在所有新化合物中，我们制备了2-羟甲基和2-氰基-1，在对血压正常的大鼠的低血压和戊巴比妥麻醉的狗的冠状动脉血流量增加的初步生物学评估中，发现4-二氢吡啶（IV和XXII）具有有效的活性。为了获得更有效的化合物，进行了2-羟基甲基-和2-氰基-1,4-二氢吡啶系列的优化研究。我们选择了异丙基2-氰基-3-甲氧基羰基-4-（3-硝基苯基）-6-甲基-1,
• 2-thiomethyl-substituted-pyridine and -3,5-dicarboxylates having
  申请人：Boehringer Biochemia Robin S.P.A.

  公开号：US04918087A1

  公开（公告）日：1990-04-17

  Pyridines of formula I ##STR1## wherein R.sub.1 is acetyl, benzoyl, cyano, nitro, alkoxycarbonyl or aminocarbonyl groups; R.sub.2 is an optionally substituted aryl or a heterocyclic group; and .phi. is a sulphurated residue such as alkylthio, cycloakylthio, arylthio, heteroarylthio, aminoalkylthio. Compounds I are useful in therapy in cardiovascular field.

  化学式为I的吡啶类化合物，其中R1是乙酰基、苯甲酰基、氰基、硝基、烷氧羰基或氨基羰基基团；R2是可选取的取代芳基或杂环基团；而φ是硫化残基，例如烷基硫、环烷基硫、芳基硫、杂环芳基硫、氨基烷基硫。I类化合物在心血管领域的治疗中有用。
• 2-thiomethyl-substituted-1,4-dihydropyridines, and pharmaceutical
  申请人：Boehringer Mannheim Italia, S.p.A.

  公开号：US05021436A1

  公开（公告）日：1991-06-04

  Compounds of formula I ##STR1## wherein R.sub.1 is an alkoxycarbonyl group, acetyl, benzoyl, cyano, nitro or aminocarbonyl; R.sub.2 is an optionally substituted aryl or hetaryl group; R.sub.3 is an alkoxycarbonyl group; .phi. is a thio residue such as alkylthio, cycloalkylthio, arylthio, heteroarylthio, aminoalkylthio, are described. Compounds I are useful in human therapy as antihypertensive, antiulcer, antithrombotic, antiischaemic agents.

  化合物I的式子如下：##STR1## 其中R.sub.1是烷氧羰基，乙酰基，苯甲酰基，氰基，硝基或氨基羰基；R.sub.2是可选取取代的芳基或杂芳基；R.sub.3是烷氧羰基；.phi.是硫残基，如烷基硫，环烷基硫，芳基硫，杂芳基硫，氨基烷硫。化合物I在人类治疗中作为降压，抗溃疡，抗血栓，抗缺血药物有用。
• A process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines
  申请人：BOEHRINGER MANNHEIM ITALIA S.P.A.

  公开号：EP0383320A1

  公开（公告）日：1990-08-22

  A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyri­dines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.

  一种对含有异硫脲基的外消旋 1,4-二氢吡啶进行光学分解的工艺。用光学活性酸盐化外消旋异硫脲，可产生异硫脲鎓盐的二异构体混合物，用常规技术分离各组分，可得到光学纯度为 1,4-二氢吡啶的异硫脲及其与常规酸的盐。上述光学纯度的 1,4-二氢吡啶可以进行脱硫和不同的转化，从而得到其他对映体纯度和治疗用途的 1,4-二氢吡啶。