<2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine>-4-spiro-3'-(2',3'-dihydro-1'-benzothiophene 1'-oxide) | 78685-46-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: <2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine>-4-spiro-3'-(2',3'-dihydro-1'-benzothiophene 1'-oxide)
• 英文别名: dimethyl 2,6-dimethyl-1'-oxospiro[1H-pyridine-4,3'-2H-1-benzothiophene]-3,5-dicarboxylate
• CAS: 78685-46-8
• 化学式: C₁₈H₁₉NO₅S
• 分子量: 361.419
• InChiKey: AGJWSNOUEHFNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  <2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine>-4-spiro-3'-(2',3'-dihydro-1'-benzothiophene 1'-oxide) 在 镍 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以74%的产率得到dimethyl 4-phenyl-2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Goldmann, Angewandte Chemie, 1981, vol. 93, # 9, p. 798 - 799

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 2,6-dimethyl-4-<2-(methylsulfinyl)phenyl>-pyridine-3,5-dicarboxylate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到<2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine>-4-spiro-3'-(2',3'-dihydro-1'-benzothiophene 1'-oxide)
  参考文献：
  名称：

  Synthesis, pharmacological effects, and conformation of 4,4-disubstituted 1,4-dihydropyridines

  摘要：

  4,4-Disubstituted 1,4-dihydropyridines are synthesized by intramolecular addition of sulfinyl carbanions to pyridines. These disubstituted derivatives show a loss of Ca antagonistic potency of up to three powers of 10 both in vitro on aortic rings and in vivo on anaesthetized dogs as compared to examples that are monosubstituted at the 4-position of the DHP ring. As the X-ray structure shows, the 4-aryl substituent is present not in the accustomed axial conformation, but in an equatorial one. This dramatic change in conformation could be the reason for the major loss of activity and would indicate the need for axial conformation of the aryl residue in pharmacologically active 1,4-dihydropyridines. The change in conformation was also confirmed by quantum chemical calculations (AM1).

  DOI：

  10.1021/jm00167a021

文献信息

• GOLDMANN, SIEGFRIED;BORN, LIBORIUS;KAZDA, STANISLAV;PITTEL, BERND;SCHRAMM+, J. MED. CHEM., 33,(1990) N, C. 1413-1418
  作者：GOLDMANN, SIEGFRIED、BORN, LIBORIUS、KAZDA, STANISLAV、PITTEL, BERND、SCHRAMM+

  DOI：——

  日期：——
• GOLDMANN, S., ANGEW. CHEM., 1981, 93, N 9, 798-799
  作者：GOLDMANN, S.

  DOI：——

  日期：——