N-((1S,9aS)-octahydro-1H-quinolizin-1-yl)acetamide

• 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: N-((1S,9aS)-octahydro-1H-quinolizin-1-yl)acetamide
• 英文别名: N-[(1R,9aR)-octahydro-1H-quinolizin-1-yl]acetamide；(+)-(1S,10S)-epiquinamide；(+)-epiquinamide；(-)-epiquinamide；N-[(1S,9aS)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]acetamide
• 化学式: C₁₁H₂₀N₂O
• 分子量: 196.293
• InChiKey: ZFOJLLQHJIXKHO-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-甲酰基-1-哌啶甲酸叔丁酯 在 palladium on activated charcoal sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium azide 、 四丁基氟化铵 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 58.92h， 生成 N-((1S,9aS)-octahydro-1H-quinolizin-1-yl)acetamide
  参考文献：
  名称：

  A concise synthesis of (±) and a total synthesis of (+)-epiquinamide

  摘要：

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.092

文献信息

• <i>N</i>,<i>N</i>-Acetals as <i>N</i>-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide
  作者：Marloes A. Wijdeven、Roel Wijtmans、Rutger J. F. van den Berg、Wim Noorduin、Hans E. Schoemaker、Theo Sonke、Floris L. van Delft、Richard H. Blaauw、Richard W. Fitch、Thomas F. Spande、John W. Daly、Floris P. J. T. Rutjes

  DOI：10.1021/ol801490m

  日期：2008.9.18

  A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction

  结合确定天然产物的绝对构型，提出了（+）-表喹酰胺的立体选择性合成。该序列中的关键步骤涉及对映体纯的氰醇的化学酶促形成，还原环化为相应的环状N，N-乙缩醛以及随后转化为合适的N-酰基亚胺离子前体以构建第二个环。
• A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis of Lupinine and (−)-Epiquinamide
  作者：Majdi Hajri、Clément Blondelle、Agathe Martinez、Jean-Luc Vasse、Jan Szymoniak

  DOI：10.1016/j.tetlet.2012.12.073

  日期：2013.2

  of tetrahydroquinolizinium salts, based on a hydrozirconation/iodination sequence involving 2-pyridyl alkenes, is presented. This approach was applied to the synthesis of substituted quinolizines as illustrated by the synthesis of Lupinine and (−)-Epiquinamide.

  提出了基于涉及2-吡啶基烯烃的加氢锆/碘化序列的四氢喹啉鎓盐的制备。如羽扇豆碱和（-）-表喹酰胺的合成所示，该方法已应用于取代的喹喔啉的合成。
• Total Synthesis of (+)-Epiquinamide
  作者：Marloes A. Wijdeven、Peter N. M. Botman、Roel Wijtmans、Hans E. Schoemaker、Floris P. J. T. Rutjes、Richard H. Blaauw

  DOI：10.1021/ol0515715

  日期：2005.9.1

  The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton. [reaction: see text]

  提出了新的喹oli嗪生物碱（+）-表喹酰胺的立体选择性全合成，该合成是从氨基酸I-赖氨酸亚乙基缩醛开始的。合成中的关键步骤涉及高度非对映选择性的N-酰基酰亚胺离子烯丙基化和开环复分解反应以提供双环骨架。[反应：看文字]
• Total synthesis of (+)-epiquinamide and (−)-epiepiquinamide from d-mannose
  作者：Withsakorn Sangsuwan、Boonsong Kongkathip、Pitak Chuawong、Ngampong Kongkathip

  DOI：10.1016/j.tet.2017.11.016

  日期：2017.12

  The total synthesis of (+)-epiquinamide and (−)-epiepiquinamide has been achieved starting from a 3,5-dihydroxyfuranoside synthon derived from d-mannose. The methods featured Bernet-Vasella reaction followed by Horner-Wadsworth-Emmons (HWE) reaction to provide a new chiral building block diene as the key steps. The bicyclic framework of this quinolizidine was constructed by using ring-closing metathesis

  从（d）-甘露糖衍生的3,5-二羟基呋喃糖苷合成子开始实现（+）-表喹酰胺和（-）-表位表喹酰胺的总合成。该方法的特色是Bernet-Vasella反应，然后进行Horner-Wadsworth-Emmons（HWE）反应，以提供一种新的手性结构单元二烯作为关键步骤。该喹oli嗪的双环骨架是通过闭环复分解，酯的选择性还原和分子内亲核取代环化而构建的。
• Practical Total Syntheses of Epiquinamide Enantiomers
  作者：Takashi L. Suyama、William H. Gerwick

  DOI：10.1021/ol061736p

  日期：2006.9.1

  Short and practical syntheses of epiquinamide and its enantiomer were accomplished with high overall yields and high stereoselectivity from readily available starting materials.

  表喹酰胺及其对映异构体的短而实用的合成是从容易获得的起始原料中以较高的总收率和较高的立体选择性完成的。