[(1R,9R,11S)-16-(4-tert-butylsulfanylbut-2-ynyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraen-12-yl]methoxy-triethylsilane | 1189110-56-2

• 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: [(1R,9R,11S)-16-(4-tert-butylsulfanylbut-2-ynyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraen-12-yl]methoxy-triethylsilane
• CAS: 1189110-56-2
• 化学式: C₃₈H₅₄N₂O₂S₂Si
• 分子量: 663.076
• InChiKey: DSEYCSNRLWIYAZ-KFHIMVBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R,9R,11S)-16-(4-tert-butylsulfanylbut-2-ynyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraen-12-yl]methoxy-triethylsilane 在 偶氮二异丁腈 、 tri-tert-butylstannane 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以61%的产率得到
  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：

  4-(tert-butylthio)but-2-ynal 、 (4bR,7R,8aR)-9-(4-methoxybenzyl)-7-(methylthio)-6-(((triethylsilyl)oxy)methyl)-7,8-dihydro-9H-8a,4b-(epiminoethano)carbazole 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.12h， 以96%的产率得到[(1R,9R,11S)-16-(4-tert-butylsulfanylbut-2-ynyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraen-12-yl]methoxy-triethylsilane
  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.