(1S,cis)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanol | 101978-98-7

• 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,cis)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanol
• 英文别名: 16-Hydroxymethyl-1,16-seco-eburnan (cis)；(14,15-dihydro-1,14-seco-eburnamenin-21-yl)-methanol；3-[(1S,12bS)-1-ethyl-3,4,6,7,12,12b-hexahydro-2H-indolo[2,3-a]quinolizin-1-yl]propan-1-ol
• CAS: 101978-98-7
• 化学式: C₂₀H₂₈N₂O
• 分子量: 312.455
• InChiKey: NAIJZPCKHYRADQ-UXHICEINSA-N

物化性质

• 沸点：
  486.0±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,cis)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanol 在 碘 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 以57%的产率得到(1S,17S)-17-ethyl-21-oxa-3,13-diazapentacyclo[11.8.0.01,17.02,10.04,9]henicosa-2(10),4,6,8-tetraene
  参考文献：
  名称：

  Moldvai, Istvan; Szantay Jr., Csaba; Szantay, Csaba, Heterocycles, 2001, vol. 55, # 11, p. 2147 - 2155

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,cis)-2,2-dimethylpropanoic acid 3-[1-ethyl-1-(1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine)]propyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到(1S,cis)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanol
  参考文献：
  名称：

  Stereocontrolled Elaboration of Quaternary Carbon Centers through the Asymmetric Michael-Type Alkylation of Chiral Imines/Secondary Enamines:  Enantioselective Synthesis of (+)-Vincamine

  摘要：

  An enantioselective synthesis of (+)-vincamine (1) has been developed. The key strategic element was the stereocontrolled elaboration of a quaternary carbon center (future C-20 center of 1) by using the asymmetric Michael reaction involving chiral imines/secondary enamines under neutral conditions. Thus, addition of enaminolactam (S)-12, derived from ketolactam 7 (itself prepared in four steps from commercially available tryptamine) and (S)-1-phenylethylamine, to methyl acrylate led, after hydrolytic workup, to adduct (R)-6 with a 90% stereoselectivity. The critical removal of the additional keto group of 6 was then examined. After extensive experimentation, we finally established that the most efficient deoxygenation procedure was the Wolff-Kishner reduction of the corresponding keto acid, which proceeded with a 55% yield. The cornerstone [ABD]-tricyclic lactam ester 38 thus obtained was next cyclized under Bischler-Napieralski reaction conditions to afford, after catalytic hydrogenation of the intermediary iminium perchlorate salt, a mixture of the desired, known indoloquinolizidine 5 and its epimer 39, in a ratio of 6:1, respectively. Basic treatment of 5 led to (+)-homoeburnamonine 4, which was finally converted, according to a known procedure, into our goal (+)-vincamine (1). Thus, synthesis of (+)-vincamine (1) has been achieved by a linear sequence of 15 chemical operations, starting from tryptamine, with an overall yield of 1.2%.

  DOI：

  10.1021/jo9622690

文献信息

• Reduction of Lactams to Cyclic Tertiary Amines by Sodium Borohydride
  作者：Sukhendu B. Mandal、Venkatachalam S. Giri、Satyesh C. Pakrashi

  DOI：10.1055/s-1987-28197

  日期：——

  Sodium borohydride in boiling tert-butyl alcohol/methanol reduces tertiary δ-lactams of the quinolizidine type to the corresponding amines in high yield.

  硼氢化钠在沸腾的叔丁醇/甲醇中可将喹嗪类叔代δ-内酰胺高产率还原成相应的胺。
• Reduction of lactams and thiolactams by sodium borohydride. Application in the synthesis of some alkaloids
  作者：S. B. Mandal、V. S. Giri、M. S. Sabeena、S. C. Pakrashi

  DOI：10.1021/jo00253a014

  日期：1988.9
• SZANTAY, CSABA;INCZE, MARIA;KARDOS, ZSUZSANNA;SOTI, FEREAC;HAJOS, GYORGY;+
  作者：SZANTAY, CSABA、INCZE, MARIA、KARDOS, ZSUZSANNA、SOTI, FEREAC、HAJOS, GYORGY、+

  DOI：——

  日期：——