[(2R,3S,5R)-5-[(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydroindolo[4,3-fg]quinolin-4-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate | 189179-65-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: [(2R,3S,5R)-5-[(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydroindolo[4,3-fg]quinolin-4-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 189179-65-5
• 化学式: C₃₇H₃₈N₂O₅
• 分子量: 590.719
• InChiKey: PKOOPVKTOMZQTJ-BRAMSPLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-[(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydroindolo[4,3-fg]quinolin-4-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以75%的产率得到(2R,3S,5R)-5-[(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydroindolo[4,3-fg]quinolin-4-yl]-2-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  N -Deoxyribosides of ergot alkaloids: Synthesis and biological activity

  摘要：

  N-Deoxyribosides of agroclavine (1), lysergol (2), and 9,10-dihydrolysergol (3) were prepared by SnCl4-catalyzed N-glycosylation of their TMS derivatives with 1-chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose. None of the new compounds exhibited activity against HIV. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00123-3
• 作为产物：
  描述：

  曲麦角碱 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 [(2R,3S,5R)-5-[(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydroindolo[4,3-fg]quinolin-4-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  N -Deoxyribosides of ergot alkaloids: Synthesis and biological activity

  摘要：

  N-Deoxyribosides of agroclavine (1), lysergol (2), and 9,10-dihydrolysergol (3) were prepared by SnCl4-catalyzed N-glycosylation of their TMS derivatives with 1-chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose. None of the new compounds exhibited activity against HIV. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00123-3

文献信息

• N -Deoxyribosides of ergot alkaloids: Synthesis and biological activity
  作者：Vladimír Křen、Petr Olšovský、Vladimír Havlíček、Petr Sedmera、Myriam Witvrouw、Erik De Clecq

  DOI：10.1016/s0040-4020(97)00123-3

  日期：1997.3

  N-Deoxyribosides of agroclavine (1), lysergol (2), and 9,10-dihydrolysergol (3) were prepared by SnCl4-catalyzed N-glycosylation of their TMS derivatives with 1-chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose. None of the new compounds exhibited activity against HIV. (C) 1997 Elsevier Science Ltd.