3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-methyl-1,4-dihydropyridine | 259103-76-9

• 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: 3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-methyl-1,4-dihydropyridine
• 英文别名: 2-(3-acetyl-2-fluoro-1-methyl-4H-pyridin-4-yl)-1-indol-1-ylethanone
• CAS: 259103-76-9
• 化学式: C₁₈H₁₇FN₂O₂
• 分子量: 312.344
• InChiKey: KQMAGYVBSMXSDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-methyl-1,4-dihydropyridine 在 sodium tetrahydroborate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium iodide 作用下， 以 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 反应 10.5h， 生成 4(Z)-ethylidene-6-methyl-1,5-dioxo-2,3,4,5,6,7-hexahydro-1H-3,7-methano[1,4]diazonino[1,2-a]indole
  参考文献：
  名称：

  Nucleophilic Addition of 1-Acetylindole Enolates to Pyridinium Salts. Stereoselective Formal Synthesis of (±)-Geissoschizine and (±)-Akagerine via 1,4-Dihydropyridines

  摘要：

  Addition of the enolate derived from 1-acetylindole (3) to pyridinium salt 4b followed by acid-induced cyclization of the resulting 1,4-dihydropyridine 5b in the presence of lithium iodide gives tetracyclic 3,7-methano[1,4]diazonino[1,2-alpha]indole 6b, which has subsequently been elaborated into the (E)-ethylidene derivative 7b. From this compound is reported a stereocontrolled route to (+/-)-geissoschizine, involving closure of C ring by Pummerer reaction, methanolysis of the resulting pentacyclic lactam 12, and desulfurization. A similar synthetic sequence starting from the enolate of 3 and 2-fluoropyridinium salt 15b gives access to the pentacyclic dilactam 2, which had previously been converted to (+/-)-akagerine through opening of the piperidone (D) ring.

  DOI：

  10.1021/jo9911894
• 作为产物：
  描述：

  3-乙酰基-2-氟吡啶 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-methyl-1,4-dihydropyridine
  参考文献：
  名称：

  Nucleophilic Addition of 1-Acetylindole Enolates to Pyridinium Salts. Stereoselective Formal Synthesis of (±)-Geissoschizine and (±)-Akagerine via 1,4-Dihydropyridines

  摘要：

  Addition of the enolate derived from 1-acetylindole (3) to pyridinium salt 4b followed by acid-induced cyclization of the resulting 1,4-dihydropyridine 5b in the presence of lithium iodide gives tetracyclic 3,7-methano[1,4]diazonino[1,2-alpha]indole 6b, which has subsequently been elaborated into the (E)-ethylidene derivative 7b. From this compound is reported a stereocontrolled route to (+/-)-geissoschizine, involving closure of C ring by Pummerer reaction, methanolysis of the resulting pentacyclic lactam 12, and desulfurization. A similar synthetic sequence starting from the enolate of 3 and 2-fluoropyridinium salt 15b gives access to the pentacyclic dilactam 2, which had previously been converted to (+/-)-akagerine through opening of the piperidone (D) ring.

  DOI：

  10.1021/jo9911894