N-(Benzyloxycarbonyl)-3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine | 139461-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(Benzyloxycarbonyl)-3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine
• 英文别名: 3-hydroxymethyl-N-benzyloxycarbonyl-2,2,4,4-tetramethyl-1-pyrrolidine；N-benzyloxycarbonyl-3-hydroxymethyl-2,2,4,4-tetramethyl-pyrrolidine；Benzyl 3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine-1-carboxylate
• CAS: 139461-49-7
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: ICLFJWFFUYYGMM-UHFFFAOYSA-N

物化性质

• 沸点：
  396.6±25.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(Benzyloxycarbonyl)-3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 N-(Benzyloxycarbonyl)-3-<1,2-didehydro-2-(ethoxycarbonyl)ethyl>-2,2,4,4-tetramethylpyrrolidine
  参考文献：
  名称：

  Design of modified pyrroline N-oxide derivatives as spin traps specific for hydroxyl radical

  摘要：

  Nitrones, 4-[2-(ethoxycarbonyl)ethyl]-3,3,5,5-tetramethyl-1-pyrroline N-oxide (7a) and 4-[2-(ethoxycarbonyl)ethyl]-5,5-di([H-2(3)[methyl)-3,3-dimethyl-1-pyrrolidine N-oxide (7b) have been synthesized. The ability of the nitrone (7a) to spin trap hydroxyl and superoxide radicals has been compared with nitrones 11a and 5,5-dimethyl-1-pyrroline N-oxide (DMPO, 8). Nitrone 11a bears a carbethoxy group at C-4, whereas nitrone 7a has a spacer of two methylene units between the carbethoxy and the basic nitrone ring skeleton. Nitrone 11a trapped both hydroxyl and superoxide radicals, while nitrone 7a trapped only hydroxyl radical. The hydroxyl radical adducts of 7a and 11a were more resistant toward superoxide-mediated reduction than the hydroxyl radical adduct of DMPO (8).

  DOI：

  10.1021/jo00034a020
• 作为产物：
  描述：

  ethyl ester of 3,3,5,5-tetramethyl-pyrroline-carboxylic acid 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.5h， 生成 N-(Benzyloxycarbonyl)-3-(hydroxymethyl)-2,2,4,4-tetramethylpyrrolidine
  参考文献：
  名称：

  Design of modified pyrroline N-oxide derivatives as spin traps specific for hydroxyl radical

  摘要：

  Nitrones, 4-[2-(ethoxycarbonyl)ethyl]-3,3,5,5-tetramethyl-1-pyrroline N-oxide (7a) and 4-[2-(ethoxycarbonyl)ethyl]-5,5-di([H-2(3)[methyl)-3,3-dimethyl-1-pyrrolidine N-oxide (7b) have been synthesized. The ability of the nitrone (7a) to spin trap hydroxyl and superoxide radicals has been compared with nitrones 11a and 5,5-dimethyl-1-pyrroline N-oxide (DMPO, 8). Nitrone 11a bears a carbethoxy group at C-4, whereas nitrone 7a has a spacer of two methylene units between the carbethoxy and the basic nitrone ring skeleton. Nitrone 11a trapped both hydroxyl and superoxide radicals, while nitrone 7a trapped only hydroxyl radical. The hydroxyl radical adducts of 7a and 11a were more resistant toward superoxide-mediated reduction than the hydroxyl radical adduct of DMPO (8).

  DOI：

  10.1021/jo00034a020

文献信息

• Pyrroline N-oxide derivatives
  申请人：National Research Council of Canada

  公开号：US05354871A1

  公开（公告）日：1994-10-11

  Derivatives of 3,5-substituted pyrroline N-oxides having substituents in the 4-position have been prepared, with the 4-position substituents being selected from certain ester, polyether, and alkanoyl groups, the latter having components which bind to biological substrates. These specific derivatives are effective as spin traps for different types of free radicals to form persistent nitroxide adducts of extended half life. These adducts can be characterized by ESR spectrometry technique and provide information e.g. concerning the identification of free radicals.

  已经制备了4-位置具有取代基的3,5-取代吡咯烷N-氧化物衍生物，其中4-位置取代基被选自于某些酯类、聚醚和脂肪酰基团，后者具有与生物底物结合的组分。这些特定的衍生物对于不同类型的自由基有效作为自旋陷阱，形成具有延长半衰期的持久性亚硝基加合物。这些加合物可以通过ESR光谱技术进行表征，并提供关于自由基识别的信息。
• New Derivatives of Pyrroline N-Oxides as Spin Traps
  作者：Prabhat Arya

  DOI：10.3987/com-95-7291

  日期：——

  Pyrroline-N-oxides containing maleimido (4), biotin (5a) and ether side chain (6 and 7) at the C-4 position have been synthesized starting fi om a common synthon (8).
• US5354871A
  申请人：——

  公开号：US5354871A

  公开（公告）日：1994-10-11
• Design of modified pyrroline N-oxide derivatives as spin traps specific for hydroxyl radical
  作者：Prabhat Arya、J. Campbell Stephens、David Griller、Sovitj Pou、Carroll L. Ramos、Wanida S. Pou、Gerald M. Rosen

  DOI：10.1021/jo00034a020

  日期：1992.4

  Nitrones, 4-[2-(ethoxycarbonyl)ethyl]-3,3,5,5-tetramethyl-1-pyrroline N-oxide (7a) and 4-[2-(ethoxycarbonyl)ethyl]-5,5-di([H-2(3)[methyl)-3,3-dimethyl-1-pyrrolidine N-oxide (7b) have been synthesized. The ability of the nitrone (7a) to spin trap hydroxyl and superoxide radicals has been compared with nitrones 11a and 5,5-dimethyl-1-pyrroline N-oxide (DMPO, 8). Nitrone 11a bears a carbethoxy group at C-4, whereas nitrone 7a has a spacer of two methylene units between the carbethoxy and the basic nitrone ring skeleton. Nitrone 11a trapped both hydroxyl and superoxide radicals, while nitrone 7a trapped only hydroxyl radical. The hydroxyl radical adducts of 7a and 11a were more resistant toward superoxide-mediated reduction than the hydroxyl radical adduct of DMPO (8).