(S)-1,6,7,8,9,9a-hexahydro-(4H)-quinolizin-4-one | 928145-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (S)-1,6,7,8,9,9a-hexahydro-(4H)-quinolizin-4-one
• 英文别名: (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one；(2S)-1,6,7,8,9,9a-hexahydro-quinolizin-4-one；(9aS)-1,6,7,8,9,9a-hexahydroquinolizin-4-one
• CAS: 928145-00-0
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: NYSKOVUSWSJZOY-QMMMGPOBSA-N

物化性质

• 沸点：
  313.2±12.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1,6,7,8,9,9a-hexahydro-(4H)-quinolizin-4-one 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 3.33h， 生成 (-)-senepodine G chloride
  参考文献：
  名称：

  Total Synthesis of (−)-Senepodine G and (−)-Cermizine C

  摘要：

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).

  DOI：

  10.1021/jo062067w
• 作为产物：
  描述：

  2-哌啶乙醇 在 sodium hydride 、 potassium carbonate 、 戴斯-马丁氧化剂 、 (+)-10-camphorsulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 20.25h， 生成 (S)-1,6,7,8,9,9a-hexahydro-(4H)-quinolizin-4-one
  参考文献：
  名称：

  Total Synthesis of (−)-Senepodine G and (−)-Cermizine C

  摘要：

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).

  DOI：

  10.1021/jo062067w

文献信息

• Preparation of Enantiopure Substituted Piperidines Containing 2-Alkene or 2-Alkyne Chains: Application to Total Syntheses of Natural Quinolizidine-Alkaloids
  作者：Guolin Cheng、Xinyan Wang、Deyong Su、Hui Liu、Fei Liu、Yuefei Hu

  DOI：10.1021/jo902615u

  日期：2010.3.19

  nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within

  通过使用非外消旋的Betti碱作为手性助剂，建立了制备对映体纯的含2个烯烃或2个炔烃的链取代哌啶的一般方法。关键步骤是代替传统的氢解反应，通过传统的氢解反应，通过邻甲基苯甲酸甲酯的形成，通过新颖的碱催化的N-脱苄基反应去除了辅助残基。通过这种方法，在数小时内以克为单位制备了十个含2-烯烃或2-炔烃的链取代的哌啶。为了证明该方法的有效性和产品的多功能性，使用（S）-2-烯丙基完成了天然生物碱（+）-peltierine，（-）-lasubine II和（+）-cermizine C的总合成--N -Boc-哌啶为通用成分。
• Enantiopure 2-piperidylacetaldehyde as a useful building block in the diversity-oriented synthesis of polycyclic piperidine derivatives
  作者：Elena Borsini、Gianluigi Broggini、Francesco Colombo、Maisaa Khansaa、Andrea Fasana、Simona Galli、Daniele Passarella、Elena Riva、Sergio Riva

  DOI：10.1016/j.tetasy.2011.01.008

  日期：2011.2

  Novel, simple, and convenient strategies for diversely functionalized piperidine derivatives have been developed by using different metal catalyzed reactions starting from enantiopure (R)- and (S)-2-piperidylacetaldehyde. (C) 2011 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C
  作者：Mercedes Amat、Rosa Griera、Robert Fabregat、Joan Bosch

  DOI：10.1016/j.tetasy.2008.04.022

  日期：2008.5

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.
• Total Synthesis of (−)-Senepodine G and (−)-Cermizine C
  作者：Barry B. Snider、James F. Grabowski

  DOI：10.1021/jo062067w

  日期：2007.2.1

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).