deacetylslaframine | 51704-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: deacetylslaframine
• 英文别名: (1S,6S,8aS)-6-amino-1,2,3,5,6,7,8,8a-octahydroindolizin-1-ol
• CAS: 51704-42-8
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: FUEOWQNIWDQPQO-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 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：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  deacetylslaframine 在 吡啶 、 盐酸 作用下， 生成 (1S,6S,8aS)-1-acetoxy-6-(N-acetylamino)-1,2,3,5,6,7,8,8a-octahydroindolizin
  参考文献：
  名称：

  An enantioselective synthesis of (−)-slaframine

  摘要：

  An enantioselective synthesis of (-)-slaframine (1) has been accomplished by an intramolecular azide [2 + 3] dipolar cycloaddition starting from the readily available aldehyde 12.

  DOI：

  10.1016/0040-4039(91)80195-c
• 作为产物：
  描述：

  ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate 在 palladium on activated charcoal 锂硼氢 、 正丁基锂 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 14.58h， 生成 deacetylslaframine
  参考文献：
  名称：

  Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹

  摘要：

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.

  DOI：

  10.1021/jo9908546

文献信息

• A versatile synthetic route to indolizidines, (+)-7-deoxy-6-epicastanospermine, (−)-7,8-dideoxy-6-epicastanospermine and (−)-N-acetylslaframine
  作者：Sung Ho Kang、Joon Seop Kim、Joo-Hack Youn

  DOI：10.1016/s0040-4039(98)02051-6

  日期：1998.12

  (+)-7-Deoxy-6-epicastanospermine 1, (−)-7,8-dideoxy-6-epicastanospermine 2 and (−)-N-acetylslaframine 4 have been synthesized via the stereoselective intramolecular iodocyclization of trichloroacetimidates generated from cis-olefinic allylic alcohols 7 and 15, respectively.

  （+） - 7-脱氧-6- epicastanospermine 1，（ - ） - 7,8-二脱氧-6- epicastanospermine 2和（ - ） - ñ -acetylslaframine 4已经合成通过从生成trichloroacetimidates的立体选择性分子内iodocyclization顺-烯烃烯丙基醇7和15。
• Synthesis of (-)-<i>N</i>-Acetylslaframine by C-1, C-5 Bis-hydroxyalkylation of (<i>S</i>)-2-(<i>N</i>,<i>N</i>-Dibenzylamino)-1,5-pentanediol via Highly Diastereoselective Lithiation of the Dicarbamate
  作者：Dieter Hoppe、Lars Padeken、Karin Gottschalk、Walter Guarnieri、Roland Fröhlich

  DOI：10.1055/s-2007-983724

  日期：2007.7

  (-)-N-Acetylslaframine, a stable form of the indolizidine alkaloid (-)-slaframine, has been synthesised by a new strategy. Applying highly stereoselective lithiation and substitution reactions, C-2, C-3 and C-8 of the bicyclic skeleton were introduced to an l-glutamic acid derived diol dicarbamate.

  (-)-N-Acetylslaframine 是吲哚利嗪生物碱 (-)-slaframine 的一种稳定形式，它是通过一种新策略合成的。通过高度立体选择性的锂化和取代反应，双环骨架的 C-2、C-3 和 C-8 被引入到一种由 l-谷氨酸衍生的二元醇二氨基甲酸酯中。
• Enantiopure <i>N</i>-Acyldihydropyridones as Synthetic Intermediates:  Asymmetric Synthesis of (−)-Slaframine
  作者：Daniel L. Comins、Alan B. Fulp

  DOI：10.1021/ol991083v

  日期：1999.12.1

  [formula: see text] An asymmetric synthesis of (-)-slaframine and N-acetylslaframine has been accomplished starting from an enantiopure dihydropyridone building block. The oxygen-carbon bond at C-1 was incorporated with complete stereoselectivity by using an efficient phenylselenocyclocarbamation reaction.

  从对映体纯的二氢吡啶酮结构单元开始已经完成了（-）-slaframine和N-乙酰基slaframine的不对称合成。通过使用有效的苯基硒代杂环氨基甲酸酯化反应，可以完全立体选择性地结合C-1处的氧碳键。
• Carretero, Juan C.; Arrayas, Ramón Gömez, Synlett, 1999, # 1, p. 49 - 52
  作者：Carretero, Juan C.、Arrayas, Ramón Gömez

  DOI：——

  日期：——
• A novel thermolytic annulation of an oxazolidinone: an enantiospecific synthesis of (-)-slaframine
  作者：Mukund P. Sibi、James W. Christensen、Biqin Li、Paul A. Renhowe

  DOI：10.1021/jo00042a002

  日期：1992.7

  Optically pure beta-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.