6-Chloro-5-formyl-4-(3-methoxy-phenyl)-2-methyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester | 10023-82-2

• 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: 6-Chloro-5-formyl-4-(3-methoxy-phenyl)-2-methyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-chloro-5-formyl-4-(3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
• CAS: 10023-82-2
• 化学式: C₁₇H₁₈ClNO₄
• 分子量: 335.787
• InChiKey: NBUGHLPYUHCDNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 足球烯 、 6-Chloro-5-formyl-4-(3-methoxy-phenyl)-2-methyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 以 邻二氯苯 为溶剂， 反应 24.0h， 以12%的产率得到N-methyl-2-(4-(3-methoxyphenyl)-3-ethoxycarbonyl-2-chloro-6-methyl-1,4-dihydropyridin-3-yl)pyrrolidino[3',4':1,2][60]fullerene
  参考文献：
  名称：

  Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines

  摘要：

  New fulleropyrrolidines endowed with chlorine-containing biological active 1,4-dihydropyridines (1,4-DHPs) have been synthesised from the respective formyl substituted 1,4-DHPs by following Prato's procedure. The presence of the chlorine atom on C2 of the 1,4-DHP ring brings about important spectroscopical and structural differences in compounds 10a-f related to the parent hydrogen-containing 11a. The mass spectroscopy study reveals different fragmentation patterns for fulleropyrrolidines 10a-f and their precursors 1,4-DHPs, as well as with 11a. Semiempirical calculations (AMI and PM3) predict a most stable stereoisomer in all cases (RS for 10a-f) and the same RR for 11a. The presence of chlorine atom in 10a-f is responsible for the higher calculated conformational energy barriers in comparison with 11a. The geometry of:the 1,4-DHP shows that the presence of fullerene unit does not significantly alter the required conformation for biological activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.047

文献信息

• A Highly Efficient Synthesis of Optically Active Hybrid 1H-1,5-Benzodiazepine–1,4-Dihydropyridines
  作者：Francisca Rebolledo、Susana Torres

  DOI：10.1055/s-0035-1560409

  日期：——

  Abstract A series of optically active hybrid compounds, 4-aryl-3-(ethoxycarbonyl)-2-methyl-4,11-dihydro-1H-benzo[b]pyrido[2,3-e][1,4]di­azepin-6-ium salts, containing the 1H-1,5-benzodiazepine and 1,4-dihydropyridine units have been effectively synthesized by means of a coupling reaction between enantioenriched 6-chloro-5-formyl-1,4-dihydropyridine derivatives and benzene-1,2-diamine. The use of trifluoroacetic

  摘要 一系列光学活性杂化化合物，4-芳基-3-（乙氧羰基）-2-甲基-4,11-二氢-1 H-苯并[ b ]吡啶基[2,3- e ] [1,4]二氮杂-通过富含对映体的6-氯-5-甲酰基-1,4-二氢吡啶衍生物与苯之间的偶联反应已有效地合成了含有1 H -1,5-苯并二氮杂卓和1,4-二氢吡啶单元的6-盐-1,2-二胺 三氟乙酸的使用允许以非常高的产率获得相应的杂种。在该过程中未发生消旋。 一系列光学活性杂化化合物，4-芳基-3-（乙氧羰基）-2-甲基-4,11-二氢-1 H-苯并[ b ]吡啶基[2,3- e ] [1,4]二氮杂-通过富含对映体的6-氯-5-甲酰基-1,4-二氢吡啶衍生物与苯之间的偶联反应已有效地合成了含有1 H -1,5-苯并二氮杂卓和1,4-二氢吡啶单元的6-盐-1,2-二胺 三氟乙酸的使用允许以非常高的产率获得相应的杂种。在该过程中未发生消旋。

表征谱图