5-Chlorocarbonyl-4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester | 133510-16-4

• 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: 5-Chlorocarbonyl-4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
• CAS: 133510-16-4
• 化学式: C₁₆H₁₄Cl₃NO₃
• 分子量: 374.651
• InChiKey: BAFORGSPMSSTPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Chlorocarbonyl-4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 、 2,2-dimethyl-3-[N-(3,3-diphenylpropyl)-N-methylamino]propan-1-ol 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-O-[3-[3,3-diphenylpropyl(methyl)amino]-2,2-dimethylpropyl] 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

  摘要：

  A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenyl-propylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4-dihydropyridines binding site labelled by H-3-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375-lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80015-9
• 作为产物：
  描述：

  4-(2,3-二氯苯基)-1,4-二氢-2,6-二甲基-3,5-吡啶二羧酸 3-甲酯 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 5-Chlorocarbonyl-4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  非洛地平对映异构体的合成及其绝对构型的测定

  摘要：

  非洛地平1的纯对映体是通过色谱分离非对映体酯与（R）-1-（对甲苯磺酰基）-3-三苯氧基氧基丙烷-2-醇3的分离而制得的，该化合物是易于除去的手性助剂。已经通过X射线晶体学在（R）-扁桃酸酯9B上推导了绝对构型。

  DOI：

  10.1016/s0040-4039(01)93912-7