(20β)-18,19-didehydroyohimban-17-one | 54725-64-3

• 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: (20β)-18,19-didehydroyohimban-17-one
• 英文别名: trans-18,19-didehydroyohimbone；(1S,15S,20R)-3,11,12,14,15,19,20,21-octahydro-1H-yohimban-18-one
• CAS: 54725-64-3；81768-64-1；89015-73-6；93527-74-3；97995-84-1
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: FRIRDXVLZFWNRG-LXIYXOSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (20β)-18,19-didehydroyohimban-17-one 在 platinum(IV) oxide sodium tetrahydroborate 、 氢气 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 生成 育亨宾
  参考文献：
  名称：

  （±）-育亨宾和（±）-铝育亨宾的新颖的全合成

  摘要：

  （±）-育亨宾（1a）和（±）-铝育亨宾（1b）的两个生物碱的总合成是通过18,19-二氢氢化肌锭（3a和b）的区域选择性官能化完成的，它们很容易通过酰胺还原法从malalane制备光环化。

  DOI：

  10.1039/c39830001231
• 作为产物：
  描述：

  16,17,19,20-tetrahydro-17-methoxy-yohimban 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (20β)-18,19-didehydroyohimban-17-one
  参考文献：
  名称：

  Naito, Takeaki; Hirata, Yumico; Miyata, Okiko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2219 - 2226

  摘要：

  DOI：

文献信息

• Symmetry-Driven Synthesis of Indole Alkaloids: Asymmetric Total Syntheses of (+)-Yohimbine, (-)-Yohimbone, (-)-Yohimbane, and (+)-Alloyohimbane
  作者：Jeffrey Aube、Shomir Ghosh、Mehmet Tanol

  DOI：10.1021/ja00099a019

  日期：1994.10

  Total asymmetric syntheses of the target alkaloids are reported. The syntheses involve the preparation of enantiomerically pure (S,S)-1,3,3a,4,7,7a-hexahydro-2(H)-inden-2-one 7 and its meso isomer 5. Each ketone is then converted into a ring-expanded lactam using an oxaziridine synthesis/rearrangement protocol. The applications of Bischler-Napieralski ring constructions along with appropriate functional group transformations afford enantiomerically enriched alloyohimbane or yohimbane from the meso- or C-2-symmetric ketones, respectively. A cis-5,6-diacetoxy compound (18) derived from the (S,S)-ketone served as the starting material for the total syntheses of the more highly functionalized alkaloids. Accordingly, a site-specific insertion of the indole-containing side chain was accomplished via stereoselective formation of an oxaziridine followed by its stereospecific rearrangement. The selectivity of this sequence allowed for the differentiation of alcohols at C-17 and C-18 (yohimbine numbering) and the synthesis of Delta 18,19-yohimbone. This alpha,beta-unsaturated ketone was converted into either (-)-yohimbone or (+)-yohimbine using standard chemistry.
• NAITO, TAKEAKI;HIRATA, YUMIKO;MIYATA, OKIKO;NINOMIYA, ICHIYA, J. CHEM. SOC. PERKIN TRANS. PTI,(1988) N 8, C. 2219-2225
  作者：NAITO, TAKEAKI、HIRATA, YUMIKO、MIYATA, OKIKO、NINOMIYA, ICHIYA

  DOI：——

  日期：——
• Naito, Takeaki; Hirata, Yumico; Miyata, Okiko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2219 - 2226
  作者：Naito, Takeaki、Hirata, Yumico、Miyata, Okiko、Ninomiya, Ichiya

  DOI：——

  日期：——
• Novel total syntheses of (±)-yohimbine and (±)-alloyohimbine
  作者：Okiko Miyata、Yumiko Hirata、Takeaki Naito、Ichiya Ninomiya

  DOI：10.1039/c39830001231

  日期：——

  The total synthesis of two alkaloids, (±)-yohimbine (1a) and (±)-alloyohimbine (1b) was completed by the regioselective functionalisation of 18,19-didehydroyohimbones (3a and b) which were readily prepared from harmalane by enamide reductive photocyclisation.

  （±）-育亨宾（1a）和（±）-铝育亨宾（1b）的两个生物碱的总合成是通过18,19-二氢氢化肌锭（3a和b）的区域选择性官能化完成的，它们很容易通过酰胺还原法从malalane制备光环化。