(+)-育亨宾 | 2671-57-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 柯楠因类生物碱
• 中文名称: (+)-育亨宾
• 英文名称: (+)-yohimbinone
• 英文别名: yohimbone；17-oxo-yohimbane-16-carboxylic acid methyl ester；15,16-Dehydrohimbinon；Yohimbinon；methyl (1S,15R,19R,20S)-18-oxo-3,11,12,14,15,16,17,19,20,21-decahydro-1H-yohimban-19-carboxylate
• CAS: 2671-57-0
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: XRPLBLPRUDFFCC-CUJLYAAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-育亨宾 在 sodium tetrahydroborate 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：

  育亨宾 在 磷酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到(+)-育亨宾
  参考文献：
  名称：

  育亨宾的合成，5.育亨宾和β-育亨宾对映体的对映选择性全合成

  摘要：

  育亨宾（1）和β-育亨宾（2）的天然和非天然对映体均已通过四环酮酸酯12的拆分步骤中的二级不对称转化合成。

  DOI：

  10.1002/jlac.198619860407

文献信息

• Enantiospecific synthesis of (−)-3-iso-19,20-dehydro-β-yohimbine from secologanin: a route to normal and pseudo stereoisomers of yohimbine
  作者：Richard T Brown、Simon B Pratt、Paul Richards

  DOI：10.1016/s0040-4039(00)00912-6

  日期：2000.7

  Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine afforded (−)-3-iso-19,20-dehydro-β-yohimbine, converted into various normal and pseudo isomers of yohimbine.

  在7的条件下水解secologanin乙缩醛导致立体选择性的羟醛环化成环己烯醛，然后用色胺将其还原胺化和环化，得到（-）-3-iso-19,20-dehydro-β-育亨宾，转化为各种正常和育亨宾的假异构体。
• 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, 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：——
• Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3-epiallo series, based on annelations of 4-methoxy-1,2-dihydropyridones
  作者：Martin E. Kuehne、Randy S. Muth

  DOI：10.1021/jo00008a025

  日期：1991.4

  N-[2-(1H-3-indolyl)ethyl]-2,3-dihydro-4-pyridone (31) was generated in two steps (77% yield) from tryptamine and N-methyl-4-piperidone methiodide. Its cyclization (90% yield) and oxidation (91% yield) provided the tetracyclic analogue 32. O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its N(a)-carbamate) furnished the dienones 38 (64%) and 43 (90%). Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 or 44. Their reductions then led to yohimbinone (52, 20% overall yield from tryptamine), alloyohimbinone (11, 19% overall yield), and 3-epi-alloyohimbinone (10, 23% overall yield), which led to yohimbine (3), beta-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).
• Bhat; Winter, Mark A.; Pearce, Molecular Pharmacology, 1995, vol. 48, # 4, p. 682 - 689
  作者：Bhat、Winter, Mark A.、Pearce、Beck, William T.

  DOI：——

  日期：——