(1S,2R,8aR)-1,2-bis-(tert-butyl-dimethylsilanyloxy)-1,2,3,5,6,8a-hexahydroindolizidine | 301805-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2R,8aR)-1,2-bis-(tert-butyl-dimethylsilanyloxy)-1,2,3,5,6,8a-hexahydroindolizidine
• 英文别名: 1,2,3,5,6,8a-Hexahydroindolizine；[(1S,2R,8aR)-1-[tert-butyl(dimethyl)silyl]oxy-1,2,3,5,6,8a-hexahydroindolizin-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 301805-17-4
• 化学式: C₂₀H₄₁NO₂Si₂
• 分子量: 383.722
• InChiKey: AGYNUUBXBXYEDQ-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,8aR)-1,2-bis-(tert-butyl-dimethylsilanyloxy)-1,2,3,5,6,8a-hexahydroindolizidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(+)-(1S,2R,8aR)-1,2,3,5,6,8a-hexahydroindolizidine-1,2-diol
  参考文献：
  名称：

  Asymmetric synthesis of indolizidine alkaloids by ring-closing–ring-opening metathesis

  摘要：

  不对称钯（0）催化的烯丙基胺化反应和钌催化的 RCMâROM 反应将容易获得的外消旋环戊烯醇 2 转化为官能化的四氢吡啶 9，后者可用于吲哚利嗪 13 的不对称合成。

  DOI：

  10.1039/b004106h
• 作为产物：
  描述：

  (-)-carbonic acid (1R,4R,5R)-4,5-isopropylidenedioxycyclopent-2-enyl ester methyl ester 在 咪唑 、 4-二甲氨基吡啶 、 potassium osmate(VI) 、 sodium periodate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 Grubbs catalyst first generation 、 N-甲基吲哚酮 、 乙烯 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-二苯基磷苯甲酰) 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.05h， 生成 (1S,2R,8aR)-1,2-bis-(tert-butyl-dimethylsilanyloxy)-1,2,3,5,6,8a-hexahydroindolizidine
  参考文献：
  名称：

  Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles

  摘要：

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00832-3

文献信息

• Asymmetric synthesis of indolizidine alkaloids by ring-closing–ring-opening metathesis
  作者：Huib Ovaa、Gijs A. van der Marel、Jacques H. van Boom、Roland Stragies、Siegfried Blechert

  DOI：10.1039/b004106h

  日期：——

  Asymmetric Pd(0) catalyzed allylic amination followed by a Ru catalyzed RCM–ROM sequence converted an easily accessible racemic cyclopentenol 2 to the functionalized tetrahydropyridine 9 which can be used for the asymmetrical synthesis of indolizidine 13.

  不对称钯（0）催化的烯丙基胺化反应和钌催化的 RCMâROM 反应将容易获得的外消旋环戊烯醇 2 转化为官能化的四氢吡啶 9，后者可用于吲哚利嗪 13 的不对称合成。
• Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles
  作者：Huib Ovaa、Christian Stapper、Gijs A van der Marel、Hermen S Overkleeft、Jacques H van Boom、Siegfried Blechert

  DOI：10.1016/s0040-4020(02)00832-3

  日期：2002.9

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.