(+/-)-6-Oxo-silicin | 60394-97-0

• 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: (+/-)-6-Oxo-silicin
• 英文别名: (3S,7R,8S)-7-ethyl-5-methyl-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),13,15,17-tetraene-2,10-dione
• CAS: 60394-97-0；63492-71-7；76231-43-1
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: HUCYTAJITIZIBC-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-<2-(methoxycarbonyl)vinyl>piridinium iodide 在 platinum(IV) oxide lithium hydroxide 、 三氯化铝 、 三甲基硅基二氢化磷酸酯 、 氢气 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 161.8h， 生成 (+/-)-6-Oxo-silicin
  参考文献：
  名称：

  A Synthetic Entry to Ervatamine Alkaloids − Synthesis of (±)-6-Oxo-16-episilicine and (±)-6-Oxosilicine

  摘要：

  Catalytic hydrogenation of several 3-acyl-4-[2-(indolyl)carbonylmethyl]-5-(methoxycarbonyl)-1,4-dihydropyridines 4 gives chemoselectively the corresponding 1,2,3,4-tetrahydropyridyl esters 5, which have been elaborated into the tetracyclic 2,3-diacylindole system 6 of oxosilicine alkaloids. Barton decarboxylation of the N-benzyl derivative 6e, followed by debenzylation and subsequent stereoselective reduction of the 5,16-double bond gives (+/-)-6-oxo-16-episilicine. This compound is converted into (+/-)-6-oxosilicine by base-catalyzed epimerization.

  DOI：

  10.1002/1099-0690(200012)2000:23<3919::aid-ejoc3919>3.0.co;2-p

文献信息

• A Synthetic Entry to Ervatamine Alkaloids − Synthesis of (±)-6-Oxo-16-episilicine and (±)-6-Oxosilicine
  作者：M.-Lluïsa Bennasar、Bernat Vidal、Rakesh Kumar、Angel Lázaro、Joan Bosch

  DOI：10.1002/1099-0690(200012)2000:23<3919::aid-ejoc3919>3.0.co;2-p

  日期：2000.12

  Catalytic hydrogenation of several 3-acyl-4-[2-(indolyl)carbonylmethyl]-5-(methoxycarbonyl)-1,4-dihydropyridines 4 gives chemoselectively the corresponding 1,2,3,4-tetrahydropyridyl esters 5, which have been elaborated into the tetracyclic 2,3-diacylindole system 6 of oxosilicine alkaloids. Barton decarboxylation of the N-benzyl derivative 6e, followed by debenzylation and subsequent stereoselective reduction of the 5,16-double bond gives (+/-)-6-oxo-16-episilicine. This compound is converted into (+/-)-6-oxosilicine by base-catalyzed epimerization.