(1S)-1-ethyl-1-(2-hydroxyethyl)-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one | 18028-54-1

• 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: (1S)-1-ethyl-1-(2-hydroxyethyl)-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one
• 英文别名: (1S)-1-ethyl-1-(2-hydroxyethyl)-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4-one
• CAS: 18028-54-1；111319-09-6；111687-22-0；111687-25-3
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: YNOQUGHPFMJVAF-GGYWPGCISA-N

物化性质

• 熔点：
  263-265 °C (decomp)
• 沸点：
  547.3±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-1-ethyl-1-(2-hydroxyethyl)-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 长春布宁
  参考文献：
  名称：

  Chiral total synthesis of indole alkaloids of the Aspidosperma and Hunteria types

  摘要：

  DOI：

  10.1021/jo00289a025

文献信息

• Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (−)-aspidospermidine and (−)-quebrachamine
  作者：John Eugene Nidhiry、Kavirayani R. Prasad

  DOI：10.1016/j.tet.2013.04.097

  日期：2013.7

  An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson–Claisen rearrangement of a chiral allyl alcohol is the main feature for the installation of the required quaternary centre.

  从乳酸描述了对映体的吲哚生物碱氨丁环胺碱，aspspersmidine和quebrachamine的全合成。所有三个生物碱的合成是从一个手性结构单元完成的。Johnson-Claisen手性烯丙醇的重排是安装所需四元中心的主要特征。
• Desymmetrization of Benzoic Acid in the Context of the Asymmetric Birch Reduction−Alkylation Protocol. Asymmetric Total Syntheses of (−)-Eburnamonine and (−)-Aspidospermidine
  作者：Arthur G. Schultz、Liping Pettus

  DOI：10.1021/jo9707592

  日期：1997.10.1

  The highly diastereoselective potassium in ammonia reduction-ethylation (EtI) of the chiral 2-(trimethylsilyl)benzamide 1b to give 1,4-cyclohexadiene 3 is the key step in asymmetric syntheses of (-)-eburnamonine (4) and (-)-aspidospermidine (5). Cyclohexadiene 3 was converted to cyclohexanone 7, which provided the trimethylsilyl-substituted butyrolactone 9 utilized for the synthesis of 4 and butyrolactone 13 required for the synthesis of 5. The preparation of 9 depended upon the completely regioselective silicon-directed Baeyer-Villiger oxidation 7-->8; Baeyer-Villiger oxidation of the cyclohexenone 10 also was regioselective to give the desired enol lactone 11 in 92% yield. Remarkable diastereoselectivity was observed for the kinetically controlled cyclization of the acyl imminium ion derived from the vinyl-substituted carboxaldehyde 16b; treatment of 16b with 5 equiv of CF3CO2H in CH2Cl2 at -55 degrees C gave an 18:1 mixture of 17 and its C(3) beta-epimer in 93% yield. The oxidation of alcohol 18 containing sensitive indole and piperidine rings was best carried out with tetrapropylammonium perruthenate/N-methylmorpholine N-oxide to give (-)-eburnamonine (4) in 97% yield. The asymmetric synthesis of (-)-aspidospermidine 5 involved the conversion of butyrolactone 13 to the hydroxylactam 22, the Harley-Mason cyclization of 22 to 23, and reduction of 23 with LiAlH4.