(+)-(8R,8aR)-perhydro-8-indolizinol

• 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: (+)-(8R,8aR)-perhydro-8-indolizinol
• 英文别名: (8R,8aR)-octahydroindolizin-8-ol；(8R,8aR)-8-indolizidinol；(8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizin-8-ol
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: GJTUCATUYQZTJZ-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-dihydro-8-hydroxy-1H-indolizinium chloride 生成 (+)-(8R,8aR)-perhydro-8-indolizinol
  参考文献：
  名称：

  SHONO, TATSUYA;MATSUMURA, YOSHIHIRO;TSUBATA, KENJI;INOUE, KENJI;NISHIDA, +, CHEM. LETT., 1983, N 1, 21-24

  摘要：

  DOI：

文献信息

• Metal-Free Decarboxylative Hetero-Diels–Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to <i>N</i>-Fused Bicyclic Hydroxypiperidine Scaffolds
  作者：Laurie-Anne Jouanno、Vincent Di Mascio、Vincent Tognetti、Laurent Joubert、Cyrille Sabot、Pierre-Yves Renard

  DOI：10.1021/jo402729a

  日期：2014.2.7

  A complete experimental and theoretical study of the thermally controlled metal-free decarboxylative hetero-Diels–Alder (HDA) reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy offers a new entry to valuable 2,6-difunctionalized 3-hydroxypyridines from readily available 2- and 4-disubstituted 5-alkoxyoxazoles. The reaction conditions proved compatible with, among others, ketone

  报道了5-烷氧基恶唑与丙烯酸热控制的无金属脱羧杂狄尔斯-阿尔德（HDA）反应的完整实验和理论研究。该策略为易于获得的2-和4-二取代的5-烷氧基恶唑提供了有价值的2,6-二官能化的3-羟基吡啶的新入口。证明该反应条件尤其与酮，酰胺，酯，醚和腈基相容。该方案具有广泛的官能团耐受性，可通过吡啶脱芳构化策略快速而通用地获得羟基吲哚并咪唑和羟基喹oli嗪衍生物。
• A NEW SYNTHETIC METHOD OF 1-AZABICYCLO[4.<i>n</i>.0]SYSTEMS
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata、Kenji Inoue、Ryoichi Nishida

  DOI：10.1246/cl.1983.21

  日期：1983.1.5

  A new method for the synthesis of bicyclic pyridinium salts from alicyclic amines and reduction of the salts to 1-azabicyclo[4.n.0]systems has been exploited.

  已经开发了一种从脂环胺合成双环吡啶鎓盐并将盐还原为 1-氮杂双环 [4.n.0] 系统的新方法。
• Stereoselective synthesis of (+)-(8R,8aR)-perhydro-8-indolizidinol
  作者：R. Sateesh Chandra Kumar、G. Venkateswar Reddy、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2011.05.102

  日期：2011.8

  A highly stereoselective total synthesis of (+)-(8R,8aR)-perhydro-8-indolizidinol is described. Key steps involved in this synthesis are diastereoselective zinc allylation, azido-olefin cyclization and reductive amination followed by cyclization which effectively constructed the indolizidine ring. This contributes a unique approach to the synthesis of indolizidine alkaloids that offers the advantages

  描述了（+）-（8 R，8a R）-过氢-8-吲哚并吲哚醇的高度立体选择性的全合成。该合成中涉及的关键步骤是非对映选择性锌烯丙基化，叠氮基烯烃环化和还原胺化，然后进行环化，从而有效地构建了吲哚并咪唑环。这为吲哚并立定生物碱的合成提供了独特的方法，该方法具有简洁性和相对较高的总收率的优点。
• Asymmetric syntheses of (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones: Two promising oxygenated indolizidine building blocks
  作者：HongKui Zhang、Xin Li、Huang Huang、PeiQiang Huang

  DOI：10.1007/s11426-011-4256-4

  日期：2011.5

  Starting from the oxygenated piperidine building block 20, two synthetic approaches to new building blocks (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones 19a/19b and 15a/15b have been developed, respectively. The first one is based on the trans-diastereoselective reductive alkylation (dr = 93:7), followed by a four-step procedure; and the second one called for the RCM reaction on the N,O-acetal derived from a vinylation, which was followed by a pyrrole formation, and a stereocontrolled cis-selective (dr = 91:9) catalytic hydrogenation. Reduction of the diastereomer 15a produced (8R,8aR)-8-indolizidinol (18).

  从含氧哌啶结构单元20开始，分别开发了两种合成新结构单元（8R,8aS）-和（8R,8aR）-8-羟基-5-吲哚嗪酮19a/19b和15a/15b的方法。第一种方法基于反式-非对映选择性还原烷基化（dr = 93:7），然后进行四步反应；第二种方法要求在乙烯化反应产生的N,O-乙缩醛上进行RCM反应，然后形成吡咯，最后进行立体选择性顺式（dr = 91:9）催化氢化。非对映异构体15a的还原反应生成（8R,8aR）-8-吲哚嗪醇（18）。
• Bond, Timothy J.; Jenkins, Robert; Ridley, Andrew C., Journal of the Chemical Society. Perkin transactions I, 1993, # 19, p. 2241 - 2242
  作者：Bond, Timothy J.、Jenkins, Robert、Ridley, Andrew C.、Taylor, Paul C.

  DOI：——

  日期：——