methyl (S)-6-((S)-(4-bromo-1H-indol-3-yl)(hydroxy)methyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate | 1161651-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (S)-6-((S)-(4-bromo-1H-indol-3-yl)(hydroxy)methyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• CAS: 1161651-73-5
• 化学式: C₁₇H₁₉BrN₂O₃
• 分子量: 379.253
• InChiKey: QLIJDXAQZTUTLR-LBAUFKAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-6-((S)-(4-bromo-1H-indol-3-yl)(hydroxy)methyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-2-[(4-bromo-1H-indol-3-yl)methyl]-1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
  参考文献：
  名称：

  Synthetic Studies toward (+)-Lysergic Acid: Construction of the Tetracyclic Ergoline Skeleton

  摘要：

  We have successfully constructed the tetracyclic skeleton of lysergic acid, which features an acylation at the C3 position of the indole as well as an intramolecular Heck reaction. The optically active D ring unit could be derived from L-pyroglutamic acid via a disrotatory electrocyclic reaction of a dibromocyclopropane.

  DOI：

  10.3987/com-08-s(d)42
• 作为产物：
  描述：

  allyl 4-bromo-3-((S)-hydroxy((S)-5-(methoxycarbonyl)-1-methyl-1,2,3,6-tetrahydropyridin-2-yl)methyl)-1H-indole-1-carboxylate 在 四氢吡咯 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (S)-6-((S)-(4-bromo-1H-indol-3-yl)(hydroxy)methyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthetic Studies toward (+)-Lysergic Acid: Construction of the Tetracyclic Ergoline Skeleton

  摘要：

  We have successfully constructed the tetracyclic skeleton of lysergic acid, which features an acylation at the C3 position of the indole as well as an intramolecular Heck reaction. The optically active D ring unit could be derived from L-pyroglutamic acid via a disrotatory electrocyclic reaction of a dibromocyclopropane.

  DOI：

  10.3987/com-08-s(d)42