3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-[2-(phenylsulfanyl)ethyl]-1,4-dihydropyridine | 220141-63-9

• 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-[2-(phenylsulfanyl)ethyl]-1,4-dihydropyridine
• 英文别名: 2-[3-acetyl-2-fluoro-1-(2-phenylsulfanylethyl)-4H-pyridin-4-yl]-1-indol-1-ylethanone
• CAS: 220141-63-9
• 化学式: C₂₅H₂₃FN₂O₂S
• 分子量: 434.534
• InChiKey: SFLYSQVTTUGWLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-[2-(phenylsulfanyl)ethyl]-1,4-dihydropyridine 在 四(三苯基膦)钯 三正丁基氢锡 、 1,8-双二甲氨基萘 、 对甲苯磺酸 、 lithium chloride 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 4(E)-ethylidene-1,5-dioxo-6-[2-(phenylsulfanyl)ethyl]-2,3,4,5,6,7-hexahydro-1H-3,7-methano[1,4]diazonino[1,2-a]indole
  参考文献：
  名称：

  Formal stereoselective synthesis of (±)-akagerine

  摘要：

  报告了五环二内酰胺 1（吲哚生物碱阿卡格瑞因的已知前体）的立体选择性合成过程，包括将 1-乙酰基吲哚 2 的烯醇加到 3-乙酰基-2-氟吡啶鎓盐 3 中，环化生成的 1,4-二氢吡啶，阐述 (E)- 乙叉取代基，并通过普默尔反应关闭 C 环。

  DOI：

  10.1039/a807868h
• 作为产物：
  描述：

  2-苯硫基乙醇 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-acetyl-2-fluoro-4-[2-(1-indolyl)-2-oxoethyl]-1-[2-(phenylsulfanyl)ethyl]-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

文献信息

• Formal stereoselective synthesis of (±)-akagerine
  作者：M.-Lluïsa Bennasar、Bernat Vidal、Bilal A. Sufi、Joan Bosch

  DOI：10.1039/a807868h

  日期：——

  A stereoselective synthesis of pentacyclic dilactam 1, a known precursor of the indole alkaloid akagerine, involving addition of the enolate of 1-acetylindole 2 to 3-acetyl-2-fluoropyridinium salt 3, cyclization of the resultant 1,4-dihydropyridine, elaboration of the (E)-ethylidene substituent and closure of the C ring by Pummerer reaction, is reported.

  报告了五环二内酰胺 1（吲哚生物碱阿卡格瑞因的已知前体）的立体选择性合成过程，包括将 1-乙酰基吲哚 2 的烯醇加到 3-乙酰基-2-氟吡啶鎓盐 3 中，环化生成的 1,4-二氢吡啶，阐述 (E)- 乙叉取代基，并通过普默尔反应关闭 C 环。
• Nucleophilic Addition of 1-Acetylindole Enolates to Pyridinium Salts. Stereoselective Formal Synthesis of (±)-Geissoschizine and (±)-Akagerine via 1,4-Dihydropyridines
  作者：M.-Lluïsa Bennasar、Juan-Miguel Jiménez、Bernat Vidal、Bilal A. Sufi、Joan Bosch

  DOI：10.1021/jo9911894

  日期：1999.12.1

  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.