bis(2-cyanoethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine 3,5-dicarboxylate | 75130-34-6

• 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: bis(2-cyanoethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine 3,5-dicarboxylate
• 英文别名: bis(2-cyanoethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate；3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3,5-bis(2-cyanoethyl) ester；bis(2-cyanoethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 75130-34-6
• 化学式: C₂₁H₂₀N₄O₆
• 分子量: 424.413
• InChiKey: UTPXNFLURSEJBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  bis(2-cyanoethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine 3,5-dicarboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 N-benzyl-3-piperidinyl 2-cyanoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Muto; Kuroda; Kawato, Arzneimittel-Forschung/Drug Research, 1988, vol. 38, # 11 A, p. 1666 - 1670

  摘要：

  DOI：

文献信息

• Protease-catalyzed enantioselective synthesis of optically active 14-dihydropyridines
  作者：Yoshihiko Hirose、Kinya Kariya、Ikuharu Sasaki、Yoshiaki Kurono、Kazuo Achiwa

  DOI：10.1016/s0040-4039(00)79178-7

  日期：1993.5

  The first enantioselective protease-catalyzed hydrolyses of 1,4-dihydropyridine-3,5-dicarboxyric diesters were developed. The monoesters obtained had high optical purity and were useful chiral building blocks which could easily lead to optically active Cablockers.

  开发了1,4-二氢吡啶-3,5-二羧基二酯的第一个对映选择性蛋白酶催化的水解物。所获得的单酯具有高的光学纯度，并且是有用的手性结构单元，其可以容易地产生光学活性的Cablockers。
• Optically active 1,4-dihydropyridine derivatives and process for preparing the same
  申请人：MERCIAN CORPORATION

  公开号：EP0636611A2

  公开（公告）日：1995-02-01

  [CONSTITUTION] Optically active 1,4-dihydropyridine derivatives represented by general formula (I), process for preparing compounds (Ic) (in general formula (I), R¹ is a lower alkyl group), process for preparing compounds represented by general formula (II) by hydrolyzing the compounds (Ic) under acidic conditions, process for preparing compounds represented by general formula (II) by solvolysis, under basic conditions, of compounds represented by general formula (III); wherein R¹ is H, a lower alkyl group, a cyanoethyl group, a lower alkanoylaminoethyl group, or a lower dialkylaminoethyl group; R² is a 2-tetrahydropyranyl group or a lower alkyloxymethyl group; R³ is a cyano group, a lower dialkylamino group or a lower alkanoylamino group; and R⁴ is a lower alkyl group. [ADVANTAGE] The compounds of general formula (I) and (II) are intermediate compounds for preparing optically active 1,4-dihydropyridine derivatives which are useful as medicines for circulatory organs. The compounds can be produced efficiently by the process of the present invention.

  [组织结构] 通式(I)代表的具有光学活性的1,4-二氢吡啶衍生物、化合物(Ic)的制备工艺（通式(I)中，R¹为低级烷基）、在酸性条件下通过水解通式(Ic)代表的化合物制备通式(II)代表的化合物的工艺、在碱性条件下通过溶解通式(III)代表的化合物制备通式(II)代表的化合物的工艺； 其中 R¹ 是 H、低级烷基、氰乙基、低级烷酰氨基乙基或低级二烷基氨基乙基；R² 是 2-四氢吡喃基或低级烷氧基甲基；R³ 是氰基、低级二烷基氨基或低级烷酰氨基；R⁴ 是低级烷基。 优点 通式(I)和(II)的化合物是制备具有光学活性的 1,4-二氢吡啶衍生物的中间化合物，这些衍生物可用作循环器官的药物。通过本发明的工艺可以高效地生产这些化合物。
• 1,4-DIHYDROPYRIDINE DERIVATIVE
  申请人：MERCIAN CORPORATION

  公开号：EP0779277A1

  公开（公告）日：1997-06-18

  Disclosed are 1,4-dihydropyridine derivatives represented by the general formula (I) and salts thereof, as well as optical active 1,4-dihydropyridine derivatives represented by the general formula (II) and salts thereof which are obtained from the derivative by biochemical reactions using microorganisms or enzymes and useful as preventive and therapeutic agents for ischemic heart diseases and hypertension. (wherein X and Y are H, NO2, CN, halogen; R1 and R2 are H, CHO, substituted alkylcarbonyl, crotonyl, cinnamoyl, alkoxycarbonyl, aryloxycarbonyl, benzyloxycarbonyl, carboxybenzoyl, or R1 and R2 taken together represent phthaloyl; n is an integer of 1 to 3).

  本发明公开了通式(I)代表的1,4-二氢吡啶衍生物及其盐，以及通式(II)代表的具有光学活性的1,4-二氢吡啶衍生物及其盐，它们是利用微生物或酶通过生化反应从衍生物中获得的，可作为缺血性心脏病和高血压的预防和治疗药物。 (其中X和Y是H、NO2、CN、卤素；R1和R2是H、CHO、取代的烷基羰基、巴豆基、肉桂酰基、烷氧基羰基、芳氧基羰基、苄氧基羰基、羧基苯甲酰基，或R1和R2合起来代表邻苯二甲酰；n是1至3的整数）。
• Carbamoylmethyl group as an activated group in protease- and base-catalyzed transesterification of 1,4-dihydropyridines: A novel asymmetric synthesis of valnidipine
  作者：Yoshihiko Hirose、Kinya Kariya、Ikuharu Sasaki、Yoshiaki Kurono、Kazuo Achiwa

  DOI：10.1016/s0040-4039(00)73813-5

  日期：1993.9

  The first protease-catalyzed enantioselective transesterification of 1,4-dihydropyridine-3,5-dicarboxylates in an aqueous solution was developed with high optical purity. Carbamoylmethyl ester group was enantioselectively transesterificated with (S)-N-benzyl-3-pyrroridinol by the protease and successive base-catalyzed transesterification proceeded smoothly to give the chiral drug, valnidipine, in a good yield.
• MUTO, K.;KURODA, T.;KAWATO, H.;NISHIKAWA, H.;NAKAMIZO, N., ARZNEIM.-FORSCH., 38,(1988) N1A, C. 1666-1670
  作者：MUTO, K.、KURODA, T.、KAWATO, H.、NISHIKAWA, H.、NAKAMIZO, N.

  DOI：——

  日期：——