(3R,4R,4aR,6aS,11aS,11bR)-11-Acetyl-6a-[2-(acetyl-methyl-amino)-ethyl]-6-hydroxy-3-methyl-1,3,4,4a,5,6,6a,11,11a,11b-decahydro-2-oxa-11-aza-benzo[a]fluorene-4-carboxylic acid methyl ester | 622369-94-2

• 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: (3R,4R,4aR,6aS,11aS,11bR)-11-Acetyl-6a-[2-(acetyl-methyl-amino)-ethyl]-6-hydroxy-3-methyl-1,3,4,4a,5,6,6a,11,11a,11b-decahydro-2-oxa-11-aza-benzo[a]fluorene-4-carboxylic acid methyl ester
• 英文别名: methyl (3R,4R,4aR,6aS,11aS,11bR)-11-acetyl-6a-[2-[acetyl(methyl)amino]ethyl]-6-hydroxy-3-methyl-1,3,4,4a,5,6,11a,11b-octahydropyrano[3,4-a]carbazole-4-carboxylate
• CAS: 622369-94-2
• 化学式: C₂₅H₃₄N₂O₆
• 分子量: 458.555
• InChiKey: NNLSXDRYNDRKMM-BQDBWWRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R,4aR,6aS,11aS,11bR)-11-Acetyl-6a-[2-(acetyl-methyl-amino)-ethyl]-6-hydroxy-3-methyl-1,3,4,4a,5,6,6a,11,11a,11b-decahydro-2-oxa-11-aza-benzo[a]fluorene-4-carboxylic acid methyl ester 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以225 mg的产率得到(3R,4R,4aR,6aS,11aS,11bR)-11-Acetyl-6a-[2-(acetyl-methyl-amino)-ethyl]-3-methyl-6-oxo-1,3,4,4a,5,6,6a,11,11a,11b-decahydro-2-oxa-11-aza-benzo[a]fluorene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of modulators of chloroquine resistance in Plasmodium falciparum, analogues of malagashanine from strychnobrasiline

  摘要：

  The syntheses of three malagashanine analogues are reported. They involve conversion of strychnobrasiline in multiple steps and obtaining (i) unsaturation of the bond 3-14, (ii) inversion of configuration on carbon C3, (iii) inversion of configuration on carbon C3 and reduction of the benzene ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.068
• 作为产物：
  描述：

  N-[2-[(1S,2S,10S,11R,14R,15R,19R)-9-acetyl-14-methyl-16-oxo-13,17-dioxa-9-azapentacyclo[9.6.2.02,10.03,8.015,19]nonadeca-3,5,7-trien-2-yl]ethyl]-N-methylacetamide 在 氢氧化钾 、 silica gel 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 8.0h， 生成 (3R,4R,4aR,6aS,11aS,11bR)-11-Acetyl-6a-[2-(acetyl-methyl-amino)-ethyl]-6-hydroxy-3-methyl-1,3,4,4a,5,6,6a,11,11a,11b-decahydro-2-oxa-11-aza-benzo[a]fluorene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of modulators of chloroquine resistance in Plasmodium falciparum, analogues of malagashanine from strychnobrasiline

  摘要：

  The syntheses of three malagashanine analogues are reported. They involve conversion of strychnobrasiline in multiple steps and obtaining (i) unsaturation of the bond 3-14, (ii) inversion of configuration on carbon C3, (iii) inversion of configuration on carbon C3 and reduction of the benzene ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.068