(3S,5S,11R,12S)-12-hydroxymethyl-5-phenyl-3,4,5,11-tetrahydrofuro[3,4-c]-β-carbolin-2(12H)-one

• 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: (3S,5S,11R,12S)-12-hydroxymethyl-5-phenyl-3,4,5,11-tetrahydrofuro[3,4-c]-β-carbolin-2(12H)-one
• 英文别名: (2R,3S,6S,8S)-3-(hydroxymethyl)-8-phenyl-4-oxa-7,10-diazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),11,13,15-tetraen-5-one
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: ACWPHZUOACYNLK-NWGLXNPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4S,5S)-5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-carboxylic acid 在 palladium on activated charcoal 咪唑 、 二苯基磷酸 、 水 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 73.0h， 生成 (3S,5S,11R,12S)-12-hydroxymethyl-5-phenyl-3,4,5,11-tetrahydrofuro[3,4-c]-β-carbolin-2(12H)-one
  参考文献：
  名称：

  Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines

  摘要：

  A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-beta-carbolines. The chirality Of D-glyceraldehyde or that of the Garner's aldehyde ensured a high and predictable diastereocontrol of the additional newly created stereocentres. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.008

文献信息

• Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines
  作者：Emmanuel Dardennes、Árpád Kovács-Kulyassa、Michel Boisbrun、Christian Petermann、Jean-Yves Laronze、Janos Sapi

  DOI：10.1016/j.tetasy.2005.02.008

  日期：2005.4

  A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-beta-carbolines. The chirality Of D-glyceraldehyde or that of the Garner's aldehyde ensured a high and predictable diastereocontrol of the additional newly created stereocentres. (c) 2005 Elsevier Ltd. All rights reserved.