tert-butyl (1R,9S,11S)-12-(hydroxymethyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraene-16-carboxylate | 1189110-53-9

• 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: tert-butyl (1R,9S,11S)-12-(hydroxymethyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraene-16-carboxylate
• CAS: 1189110-53-9
• 化学式: C₂₉H₃₆N₂O₄S
• 分子量: 508.682
• InChiKey: BMFVGQXUVDOLNX-RFYMFKDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,9S,11S)-12-(hydroxymethyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraene-16-carboxylate 、 三乙基硅基三氟甲磺酸酯 以 乙腈 为溶剂， 反应 0.2h， 以84%的产率得到(4bR,7R,8aR)-9-(4-methoxybenzyl)-7-(methylthio)-6-(((triethylsilyl)oxy)methyl)-7,8-dihydro-9H-8a,4b-(epiminoethano)carbazole
  参考文献：
  名称：

  Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine

  摘要：

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

  DOI：

  10.1021/ja906472m
• 作为产物：
  描述：

  丙炔醛 、 tert-butyl 2-(1-(4-methoxybenzyl)-2-((E)-2-(methylthio)vinyl)-1H-indol-3-yl)ethylcarbamate 在 C₂HBr₃O₂*C₁₉H₂₄N₂O 、 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 作用下， 以 乙醚 、 甲苯 、 甲醇 为溶剂， 反应 36.5h， 以87%的产率得到tert-butyl (1R,9S,11S)-12-(hydroxymethyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraene-16-carboxylate
  参考文献：
  名称：

  Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine

  摘要：

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

  DOI：

  10.1021/ja906472m

文献信息

• Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
  作者：Spencer B. Jones、Bryon Simmons、David W. C. MacMillan

  DOI：10.1021/ja906472m

  日期：2009.9.30

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.