(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,5-tetrahydro-pyridine 1-oxide | 519189-08-3

• 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: (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,5-tetrahydro-pyridine 1-oxide
• 英文别名: tert-butyl-[[(3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-1-oxido-2,3,4,5-tetrahydropyridin-1-ium-5-yl]oxy]-dimethylsilane
• CAS: 519189-08-3
• 化学式: C₁₇H₃₇NO₃Si₂
• 分子量: 359.657
• InChiKey: OIXBCWIWLARTIU-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,5-tetrahydro-pyridine 1-oxide 在 palladium dihydroxide 作用下， 反应 20.0h， 生成 (1R,2R,6R,8R,8aS)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-oxo-octahydro-indolizine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

  摘要：

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02336-5
• 作为产物：
  描述：

  2-(Phenylsulfonyl)-3-phenyloxaziridin 、 (3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine 以100%的产率得到(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,5-tetrahydro-pyridine 1-oxide
  参考文献：
  名称：

  A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

  摘要：

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02336-5