(1S,6S,8aS)-1-acetoxy-6-(N-acetylamino)-1,2,3,5,6,7,8,8a-octahydroindolizin | 41563-75-1

• 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: (1S,6S,8aS)-1-acetoxy-6-(N-acetylamino)-1,2,3,5,6,7,8,8a-octahydroindolizin
• 英文别名: (1S,6S,8aS)-6-(acetylamino)octahydroindolizin-1-yl acetate；N-acetylslaframine；[(1S,6S,8aS)-6-acetamido-1,2,3,5,6,7,8,8a-octahydroindolizin-1-yl] acetate
• CAS: 41563-75-1
• 化学式: C₁₂H₂₀N₂O₃
• 分子量: 240.302
• InChiKey: UQNSGOYQGBXKSN-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Methanesulfonic acid (S)-3-((2S,3R)-2-benzenesulfonylmethyl-3-triisopropylsilanyloxy-pyrrolidin-1-yl)-2-hydroxy-propyl ester 在 platinum(IV) oxide 吡啶 、 咪唑 、 盐酸 、 草酰氯 、 盐酸羟胺 、 水 、 氢气 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 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：

  Carretero, Juan C.; Arrayas, Ramón Gömez, Synlett, 1999, # 1, p. 49 - 52

  摘要：

  DOI：

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。
• Enantioselective Allyltitanation. Synthesis of (-)-Slaframine
  作者：Janine Cossy、Catherine Willis、Véronique Bellosta、Laurent Saint-Jalmes

  DOI：10.1055/s-2002-28505

  日期：——

  An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine from aldehyde 1 is reported. The stereogenic centers at C-1 and C-8a are introduced by an enantioselective allyltitanation and a Mitsunobu reaction. Reductive double cyclization of the acyclic compound (-)-10 affords the bicyclic skeleton of (-)-slaframine.

  报告了从醛 1 对吲哚利嗪生物碱 (-)-slaframine 的对映选择性合成。通过对映选择性烯丙基钛化和 Mitsunobu 反应引入了 C-1 和 C-8a 的立体中心。无环化合物 (-)-10 的还原双环化反应生成了 (-)-slaframine 的双环骨架。
• Radical routes to indolizidines. Synthesis of (-)-slaframine
  作者：Spencer Knapp、Frank S. Gibson

  DOI：10.1021/jo00044a011

  日期：1992.8

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.