(6aR,6'aR,9R,9'S)-dimethyl-7,7'-dimethyl-4,4',6,6a,6',6a',7,7',8,8',9,9'-dodecahydro-9,9'-biindolo[4,3-fg]quinoline-9,9'-dicarboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aR,6'aR,9R,9'S)-dimethyl-7,7'-dimethyl-4,4',6,6a,6',6a',7,7',8,8',9,9'-dodecahydro-9,9'-biindolo[4,3-fg]quinoline-9,9'-dicarboxylate
• 英文别名: methyl (6aR,9S)-9-[(6aR,9R)-9-methoxycarbonyl-7-methyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinolin-9-yl]-7-methyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinoline-9-carboxylate
• 化学式: C₃₄H₃₄N₄O₄
• 分子量: 562.668
• InChiKey: SHKQZTKLIUBVSJ-FSUFCWANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  麦角酸 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (6aR,6'aR,9R,9'S)-dimethyl-7,7'-dimethyl-4,4',6,6a,6',6a',7,7',8,8',9,9'-dodecahydro-9,9'-biindolo[4,3-fg]quinoline-9,9'-dicarboxylate
  参考文献：
  名称：

  Dimerization of (+)-Lysergic Acid Esters

  摘要：

  Dimer isomer mixtures, characterized by a bridgehead C8-C8' bond, (6a-7a; 6b-7b) were obtained from (+)-lysergic acid methyl or ethyl ester (1b; 1c) in a solution of methanol or ethanol. The isomers were separated, and their structures were determined by detailed NMR measurements and X-ray analysis. Density functional theory was applied to provide insight into the reaction mechanism. Based on an extended examination and the theoretical calculations, a plausible reaction sequence leading to dimers is also presented. The proposed mechanism has been verified by detecting the formation of the superoxide radical anion (O-2(center dot-)).

  DOI：

  10.3987/com-07-11011

文献信息

• Dimerization of (+)-Lysergic Acid Esters
  作者：István Moldvai、Luca Russo、Kari Rissanen、Julianna Kardos、Eszter Gács-Baitz、Eszter Termesvári-Major、Imre Pápai、Éva Szárics、Csaba Szántay

  DOI：10.3987/com-07-11011

  日期：——

  Dimer isomer mixtures, characterized by a bridgehead C8-C8' bond, (6a-7a; 6b-7b) were obtained from (+)-lysergic acid methyl or ethyl ester (1b; 1c) in a solution of methanol or ethanol. The isomers were separated, and their structures were determined by detailed NMR measurements and X-ray analysis. Density functional theory was applied to provide insight into the reaction mechanism. Based on an extended examination and the theoretical calculations, a plausible reaction sequence leading to dimers is also presented. The proposed mechanism has been verified by detecting the formation of the superoxide radical anion (O-2(center dot-)).