(1S,2S,10S,11R,14R,15R,16S,19R)-14-methyl-2-[2-(methylamino)ethyl]-13,17-dioxa-9-azapentacyclo[9.6.2.02,10.03,8.015,19]nonadeca-3,5,7-trien-16-ol | 234114-52-4

• 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: (1S,2S,10S,11R,14R,15R,16S,19R)-14-methyl-2-[2-(methylamino)ethyl]-13,17-dioxa-9-azapentacyclo[9.6.2.02,10.03,8.015,19]nonadeca-3,5,7-trien-16-ol
• CAS: 234114-52-4
• 化学式: C₂₀H₂₈N₂O₃
• 分子量: 344.454
• InChiKey: YTMSNDCXWHQJAE-VOSDVNMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  62.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,10S,11R,14R,15R,16S,19R)-14-methyl-2-[2-(methylamino)ethyl]-13,17-dioxa-9-azapentacyclo[9.6.2.02,10.03,8.015,19]nonadeca-3,5,7-trien-16-ol 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 重铬酸吡啶 、 氢气 、 silica gel 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 methyl (1S,5S,7R,8R,9R,12R,13S)-4,9-dimethyl-10-oxa-4,14-diazapentacyclo[11.7.0.01,5.07,12.015,20]icosane-8-carboxylate
  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：

  strychnobrasiline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S,10S,11R,14R,15R,16S,19R)-14-methyl-2-[2-(methylamino)ethyl]-13,17-dioxa-9-azapentacyclo[9.6.2.02,10.03,8.015,19]nonadeca-3,5,7-trien-16-ol
  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

文献信息

• New indolines derivatives from strychnobrasiline, modulators of chloroquine resistance in Plasmodium falciparum
  作者：François Trigalo、Marie-Thérèse Martin、Alain Blond、Jean-Paul Brouard、Herintsoa Rafatro、David Ramanitrahasimbola、François Frappier

  DOI：10.1016/s0040-4020(99)00269-0

  日期：1999.5

  An unexpected molecular rearrangement in lithium aluminium hydride reduction of the indole alkaloid strychnobrasiline was observed. The resulting derivatives obtained were evaluated as modulators of chloroquine resistance in Plasmodium falciparum. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of modulators of chloroquine resistance in Plasmodium falciparum, analogues of malagashanine from strychnobrasiline
  作者：François Trigalo、Roger Joyeau、Van Cuong Pham、Jean Jacques Youté、Philippe Rasoanaivoa、François Frappier

  DOI：10.1016/j.tet.2004.04.068

  日期：2004.6

  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.