7-hydroxyhexahydroindolizin-3(2H)-one

• 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: 7-hydroxyhexahydroindolizin-3(2H)-one
• 英文别名: 1-Aza-4-hydroxy-bicyclo<4.3.0>nonan-9-on；7-hydroxy-hexahydro-indolizin-3-one；7-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: STJZDQPLOKWGDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-hydroxyhexahydroindolizin-3(2H)-one 、 乙酸酐 在 吡啶 作用下， 生成 (7R*,8aR*)-3-oxooctahydroindolizin-7-yl acetate 、 7α-acetoxy-3-indolizidinone
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  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.

  DOI：

  10.1021/jo00044a011
• 作为产物：
  描述：

  5-(iodomethyl)-2-pyrrolidinone 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 三氟乙酸 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 12.0h， 生成 7-hydroxyhexahydroindolizin-3(2H)-one
  参考文献：
  名称：

  碘代内酰胺的自由基基环

  摘要：

  碘代内酰胺与反应性烷基卤化物的N-烷基化，或衍生的硒代内酰胺与反应性较低烷基卤化物的N-烷基化，导致底物被自由基引发环化为吡咯烷二酮和吲哚并二酮，例如2 → 3。描述了碘化物/溴乙烯，硒化物/醛和硒化物/氯乙烯自由基环化的第一个实例。

  DOI：

  10.1016/s0040-4039(00)97856-0

文献信息

• Radical based annulations of iodo lactams
  作者：Spencer Knapp、Frank S Gibson、Yun H Choe

  DOI：10.1016/s0040-4039(00)97856-0

  日期：1990.1

  N-Alkylation of iodo lactams with reactive alkyl halides, or of the derived selenide lactams with less reactive alkyl halides, leads to substrates for free radical initiated cyclization to pyrrolizidinones and indolizidinones, e. g. 2 → 3. The first examples of iodide / vinyl bromide, selenide / aldehyde, and selenide / vinyl chloride radical cyclizations are described.

  碘代内酰胺与反应性烷基卤化物的N-烷基化，或衍生的硒代内酰胺与反应性较低烷基卤化物的N-烷基化，导致底物被自由基引发环化为吡咯烷二酮和吲哚并二酮，例如2 → 3。描述了碘化物/溴乙烯，硒化物/醛和硒化物/氯乙烯自由基环化的第一个实例。
• [EN] TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR<br/>[FR] COMPOSÉ TRICYCLIQUE SERVANT D'IMMUNOMODULATEUR<br/>[ZH] 作为免疫调节剂的三并环化合物
  申请人：CHIA TAI TIANQING PHARMACEUTICAL GROUP CO LTD

  公开号：WO2017140274A1

  公开（公告）日：2017-08-24

  提供了一种通式I和通式II的化合物或其药学上可接受的盐及其药物组合物，所述通式I和通式II的化合物或其药学上可接受的盐及其药物组合物具有吲哚2,3-双加氧酶（IDO）抑制活性，能治疗由吲哚2,3-双加氧酶（IDO）介导的免疫抑制疾病，如传染性疾病或癌症。
• [EN] PYRAZOLOPYRIDINE COMPOUNDS AS TAM INHIBITORS<br/>[FR] COMPOSÉS DE PYRAZOLOPYRIDINE COMME INHIBITEURS DE TAM
  申请人：[en]SHANGHAI ANTENGENE CORPORATION LIMITED

  公开号：WO2023051464A1

  公开（公告）日：2023-04-06

  The present disclosure relates to pyrazolopyridine compounds useful as inhibitors of TAM kinases, in particular as intibitors of AXL and MER kinases, as well as pharmaceutical compositions comprising these compounds and methods of treatment by administration of these compounds or the pharmaceutical compositions.
• 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.