(+/-)-5-epi-cermizine C

• 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: (+/-)-5-epi-cermizine C
• 英文别名: (±)-epi-cermizine C；(+/-)-epi-cermizine C；(2R,4S,9aR)-2,4-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: KXIIYBCOPLMAKO-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-5-epi-cermizine C 、 三氟乙酸 以 甲醇 为溶剂， 以100%的产率得到(±)-(2R,4S,9aR)-2,4-dimethyloctahydro-2H-quinolizine 2,2,2-trifluoroacetate
  参考文献：
  名称：

  (±)-cermizine D 的实际全合成和 (±)-cermizine C 的正式合成

  摘要：

  实现了 (±)-cermizine D 的实际全合成和 (±)-cermizine C 的正式合成。四步全合成主要包括迈克尔加成、Weinreb 酰胺活化取代和一系列缩酮化/PtO2 催化的脱芳构化/还原胺化反应，导致闭环，总产率为 13.7%。正式合成以29.7%的总产率完成。

  DOI：

  10.3184/174751918x15271572210923
• 作为产物：
  描述：

  octahydro-2-methyl-(4H)-quinolizin-4-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.67h， 生成 (+/-)-5-epi-cermizine C
  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

• Enantioselective Approach to Quinolizidines: Total Synthesis of Cermizine D and Formal Syntheses of Senepodine G and Cermizine C
  作者：Nagarathanam Veerasamy、Erik C. Carlson、Nathan D. Collett、Mrinmoy Saha、Rich G. Carter

  DOI：10.1021/jo400324t

  日期：2013.5.17

  The formal syntheses of C5-epi-senepodine G and C5-epi-cermizine C have been accomplished through a novel diastereoselective, intramolecular amide Michael addition process. The total synthesis of cermizine D has been achieved through use of an organocatalyzed, heteroatom Michael addition to access a common intermediate. Additional key steps of this sequence include a matched, diastereoselective alkylation

  C的正式合成5 -外延-senepodine G和C 5 -外延-cermizine C 是通过一种新型的非对映选择性、分子内酰胺迈克尔加成过程完成的。cermizine D 的全合成是通过使用有机催化的杂原子迈克尔加成获得常见中间体来实现的。该序列的其他关键步骤包括使用碘甲基苯硫醚和砜-醛偶联/还原脱硫序列进行匹配的非对映选择性烷基化，以结合主要亚基。已经在功能密集的耦合伙伴上探索了 Hartwig 式 C-N 耦合的效用。已经研究了对 α,β-不饱和砜的非对映选择性共轭加成，这仅通过六步即可从市售起始材料中提供关键的砜中间体。N -Boc 保护的哌啶砜。
• Straightforward Access to Enantioenriched 2-Allylpiperidine: Application to the Synthesis of Alkaloids
  作者：Irene Bosque、José C. González-Gómez、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo202211u

  日期：2012.1.6

  requires only two synthetic operations with one-column chromatography and is readily scaled up. The versatility of these chiral building blocks was exemplified by the total or formal synthesis of some natural and unnatural alkaloids.

  的有效立体控制准备（2 - [R ，- [R小号）-2-烯丙基- （ñ -叔丁基亚）哌啶及其对映体中详述。该序列仅需使用一柱色谱进行两次合成操作，即可轻松按比例放大。这些手性结构单元的多功能性以某些天然和非天然生物碱的全部或正式合成为例。
• Conjugate Addition of Lithiated Methyl Pyridines to Enones
  作者：Douglass F. Taber、Pengfei Guo、Michael T. Pirnot

  DOI：10.1021/jo100890s

  日期：2010.8.20

  Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (+/-)-senepodine G and (+/-)-cermizine C.
• A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C
  作者：Xin Shi、Ying Bao、Zhen-Tao Deng、Yu Zhu、Li-Dong Shao、Hong-Bin Zhang、Qin-Shi Zhao

  DOI：10.3184/174751918x15271572210923

  日期：2018.6

  A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C were achieved. The four-step total synthesis comprised mainly a Michael addition, a Weinreb amide-activated substitution and a sequence of ketalation/PtO2-catalysed dearomatisation/reductive amination reactions that resulted in ring closure in 13.7% overall yield. The formal synthesis was accomplished in 29.7%

  实现了 (±)-cermizine D 的实际全合成和 (±)-cermizine C 的正式合成。四步全合成主要包括迈克尔加成、Weinreb 酰胺活化取代和一系列缩酮化/PtO2 催化的脱芳构化/还原胺化反应，导致闭环，总产率为 13.7%。正式合成以29.7%的总产率完成。
• 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).