danuphylline | 213478-78-5

• 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: danuphylline
• 英文别名: dimethyl (1R,12S,15R,20S)-19-formyl-22-oxo-6,8-dioxa-11,19-diazahexacyclo[13.5.3.01,12.02,10.05,9.015,20]tricosa-2(10),3,5(9)-triene-11,12-dicarboxylate
• CAS: 213478-78-5
• 化学式: C₂₄H₂₆N₂O₈
• 分子量: 470.479
• InChiKey: JHZSPIZZIWORMX-GDKQOWJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  danuphylline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1R,12S,15R,20S)-22-hydroxy-12-(hydroxymethyl)-6,8-dioxa-11,19-diazahexacyclo[13.5.3.01,12.02,10.05,9.015,20]tricosa-2(10),3,5(9)-triene-19-carbaldehyde
  参考文献：
  名称：

  Danuphylline, a novel pentacyclic indole from Kopsia

  摘要：

  A novel pentacyclic indole alkaloid, danuphylline, was obtained from the leaf-extract of Kopsia dasyrachis and its structure elucidated by spectral analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01150-2
• 作为产物：
  描述：

  methyl 11,12-methylenedioxychanofruticosinate 在 2,6-二甲基吡啶 、 高氯酸四乙基铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以5%的产率得到dimethyl (1R,4S,15R,16S,19S)-18,20-dioxo-8,10-dioxa-5,17-diazaheptacyclo[15.4.3.01,16.04,15.06,14.07,11.015,19]tetracosa-6(14),7(11),12-triene-4,5-dicarboxylate
  参考文献：
  名称：

  Structure and biomimetic, electrochemically-mediated semisynthesis of the novel pentacyclic indole danuphylline

  摘要：

  structure of the novel pentacyclic indole, danuphylline, from Kopsia dasyrachis was established by spectral analysis. Anodic oxidation of the hexacylic alkaloid methyl 11,12-methylenedioxychanofruticosinate on platinum in TEAP/MeCN-CH2Cl2 (2 F mol(-1)) yielded an iminium ion salt which on silica gel chromatography underwent a facile retro-aldol process to give danuphylline. Allowing the oxidation to proceed until consumption of 4 F mol(-1) of charge resulted in an unprecedented electrochemically-mediated aromatic chlorination yielding 10-chloro-danuphylline. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01125-9

文献信息

• Danuphylline, a novel pentacyclic indole from Kopsia
  作者：Toh-Seok Kam、Tuck-Meng Lim、Yeun-Mun Choo、G. Subramaniam

  DOI：10.1016/s0040-4039(98)01150-2

  日期：1998.8

  A novel pentacyclic indole alkaloid, danuphylline, was obtained from the leaf-extract of Kopsia dasyrachis and its structure elucidated by spectral analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Structure and biomimetic, electrochemically-mediated semisynthesis of the novel pentacyclic indole danuphylline
  作者：Toh-Seok Kam、Tuck-Meng Lim、Yeun-Mun Choo

  DOI：10.1016/s0040-4020(98)01125-9

  日期：1999.1

  structure of the novel pentacyclic indole, danuphylline, from Kopsia dasyrachis was established by spectral analysis. Anodic oxidation of the hexacylic alkaloid methyl 11,12-methylenedioxychanofruticosinate on platinum in TEAP/MeCN-CH2Cl2 (2 F mol(-1)) yielded an iminium ion salt which on silica gel chromatography underwent a facile retro-aldol process to give danuphylline. Allowing the oxidation to proceed until consumption of 4 F mol(-1) of charge resulted in an unprecedented electrochemically-mediated aromatic chlorination yielding 10-chloro-danuphylline. (C) 1999 Elsevier Science Ltd. All rights reserved.