exo-2-(t-butoxycarbonyl)-7-(methoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-ene | 134107-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: exo-2-(t-butoxycarbonyl)-7-(methoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-ene
• 英文别名: 2-tert-butyl 6-methyl (1RS,4RS,6SR)-2-azabicyclo[2.2.2]oct-7-ene-2,6-dicarboxylate；rel-2-(1,1-Dimethylethyl) 6-methyl (1R,4R,6S)-2-azabicyclo[2.2.2]oct-7-ene-2,6-dicarboxylate；2-O-tert-butyl 6-O-methyl (1R,4R,6S)-2-azabicyclo[2.2.2]oct-7-ene-2,6-dicarboxylate
• CAS: 134107-78-1
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: NRRIDVLOIXRRBO-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  exo-2-(t-butoxycarbonyl)-7-(methoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-ene 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 72.0h， 生成 1-tert-butyl 2,3,5-trimethyl 1,r-2,t-3,c-5-piperidinetetracarboxylate
  参考文献：
  名称：

  Stereospecific synthesis of new 2,3,4,5-piperidinetetracarboxylic acids and 2,3,5-piperidinetricarboxylic acids

  摘要：

  Diels-Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new r-2,c-3,c-4,c-5-piperidinetetracarboxylic acid, r-2,t-3,t-4,c-5-piperidinetetracarboxylic acid, r-2,c-3,c-5-piperidinetricarboxylic acid, and r-2,t-3,c-5-piperidinetricarboxylic acid. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01200-6
• 作为产物：
  描述：

  1,2-二氢-1-吡啶羧酸甲酯 在 碘代三甲硅烷 作用下， 以 四氯化碳 为溶剂， 反应 129.0h， 生成 exo-2-(t-butoxycarbonyl)-7-(methoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-ene
  参考文献：
  名称：

  Stereospecific synthesis of new 2,3,4,5-piperidinetetracarboxylic acids and 2,3,5-piperidinetricarboxylic acids

  摘要：

  Diels-Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new r-2,c-3,c-4,c-5-piperidinetetracarboxylic acid, r-2,t-3,t-4,c-5-piperidinetetracarboxylic acid, r-2,c-3,c-5-piperidinetricarboxylic acid, and r-2,t-3,c-5-piperidinetricarboxylic acid. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01200-6

文献信息

• Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase
  作者：Malcolm M. Campbell、Mary F. Mahon、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4020(01)89449-7

  日期：——

  The synthesis of (+/-)-5-homoshikimic acid, its 5-fluoromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-di-hydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds