(1S,8aS)-1-hydroxyhexahydroindolizin-3-one | 306739-91-3

• 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,8aS)-1-hydroxyhexahydroindolizin-3-one
• 英文别名: (1S,8aS)-1-hydroxyindolizidin-3-one；(1S,8aS)-1-hydroxyhexahydroindolizin-3(5H)-one；(1S,8aS)-1-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 306739-91-3
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: GZEVRJJSTVNDLW-BQBZGAKWSA-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：

  (1S,8aS)-1-hydroxyhexahydroindolizin-3-one 在 dimethyl sulfide borane 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到(1S,8aS)-1-Hydroxyindolizidine
  参考文献：
  名称：

  Nonracemic Bicyclic Lactam Lactones via Regio- and cis-Diastereocontrolled C−H Insertion. Asymmetric Synthesis of (8S,8aS)-Octahydroindolizidin-8-ol and (1S,8aS)-Octahydroindolizidin-1-ol

  摘要：

  The Rh-2(MPPIM)(4)-catalyzed intraniolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one proceeds with high regioselectivity and cis-diastereoselectivity to give good yields of chiral nonracemic bicyclic lactam lactones (BLLs). For (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one, the regio selectivity of the C-H insertion is catalyst-dependent; for example, (S)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one undergoes C-H insertion at C-6 preferentially when Rh-2(5S-MPPIM)(4) is used, but with Rh-2(5R-MPPIM)(4), C-H insertion occurs preferentially at C-4. This effect is not observed in the reaction of (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one. The utility of the BLLs as chiral building blocks in alkaloid synthesis is exemplified by the synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

  DOI：

  10.1021/jo901790g
• 作为产物：
  描述：

  (4S,5S)-5-but-3-enyl-3,3-dichloro-4-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidin-2-one 在 disialylborane 、 铜 、 sodium hydride 、 氯化铵 、 三乙胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (1S,8aS)-1-hydroxyhexahydroindolizin-3-one
  参考文献：
  名称：

  Highly Enantioselective Approach to Indolizidines:  Preparation of (+)-(1S,8aS)-1-Hydroxyindolizidine and (−)-Slaframine

  摘要：

  A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with achiral dienol ether.

  DOI：

  10.1021/jo0005621

文献信息

• Short Syntheses of (-)-<b>(</b> <b><i>R</i></b> <b>)</b>-Pyrrolam A and (1<b><i>S</i></b>)-1-Hydroxyindolizidin-3-one
  作者：Rainer Schobert、André Wicklein

  DOI：10.1055/s-2007-966035

  日期：——

  (-)-( R)-Pyrrolam A was prepared in five steps, 95% ee and 25% yield, from ( R)-benzyl prolinate. Closure of the pyrrolidine ring was effected by a domino addition-Wittig alkenation reaction with ylide Ph 3 PCCO, immobilized on a polystyrene resin. An indolizidinone was obtained likewise from ( R)-benzyl pipecolate. The reduction of 1-ketopyrrolizidinones and 1-ketoindolizidinones is described.

  (-)-(R)-Pyrrolam A 由 (R)-脯氨酸苄酯分五步制备，95% ee 和 25% 产率。吡咯烷环的闭合通过与叶立德 Ph 3 PCCO 的多米诺加成-维蒂希烯化反应实现，固定在聚苯乙烯树脂上。同样由(R)-苄基哌可酸得到吲哚齐酮。描述了 1-ketopyrrolizidinones 和 1-ketoindolizidinones 的还原。
• Nonracemic Bicyclic Lactam Lactones via Regio- and <i>cis</i>-Diastereocontrolled C−H Insertion. Asymmetric Synthesis of (8<i>S</i>,8a<i>S</i>)-Octahydroindolizidin-8-ol and (1<i>S</i>,8a<i>S</i>)-Octahydroindolizidin-1-ol
  作者：Andrew G. H. Wee、Gao-Jun Fan、Hypolite M. Bayirinoba

  DOI：10.1021/jo901790g

  日期：2009.11.6

  The Rh-2(MPPIM)(4)-catalyzed intraniolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one proceeds with high regioselectivity and cis-diastereoselectivity to give good yields of chiral nonracemic bicyclic lactam lactones (BLLs). For (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one, the regio selectivity of the C-H insertion is catalyst-dependent; for example, (S)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one undergoes C-H insertion at C-6 preferentially when Rh-2(5S-MPPIM)(4) is used, but with Rh-2(5R-MPPIM)(4), C-H insertion occurs preferentially at C-4. This effect is not observed in the reaction of (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one. The utility of the BLLs as chiral building blocks in alkaloid synthesis is exemplified by the synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
• Highly Enantioselective Approach to Indolizidines:  Preparation of (+)-(1<i>S</i>,8a<i>S</i>)-1-Hydroxyindolizidine and (−)-Slaframine
  作者：Mehrnaz Pourashraf、Philippe Delair、Martin O. Rasmussen、Andrew E. Greene

  DOI：10.1021/jo0005621

  日期：2000.10.1

  A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with achiral dienol ether.