1-hydroxy-4-carbamoyl-2,2,6,6,-tetramethylpiperidine methyl ester | 439858-36-3

• 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: 1-hydroxy-4-carbamoyl-2,2,6,6,-tetramethylpiperidine methyl ester
• 英文别名: 4-(methoxycarbonyl)-2,2,6,6-tetramethylpiperidin-1-yloxy；Methyl 1-hydroxy-2,2,6,6-tetramethylpiperidine-4-carboxylate
• CAS: 439858-36-3
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: MMMJKCJKQUNPKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-hydroxy-4-carbamoyl-2,2,6,6,-tetramethylpiperidine methyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以67%的产率得到1-乙酰氧基-4-甲氧羰基-2,2,6,6-四甲基哌啶
  参考文献：
  名称：

  Acyl-Protected Hydroxylamines as Spin Label Generators for EPR Brain Imaging

  摘要：

  In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.

  DOI：

  10.1021/jm0105169
• 作为产物：
  描述：

  甲醇 、 4-羧基-2,2,6,6-四甲基氮杂环己烷-1-氧基自由基 在 盐酸 作用下， 反应 0.5h， 以94%的产率得到1-hydroxy-4-carbamoyl-2,2,6,6,-tetramethylpiperidine methyl ester
  参考文献：
  名称：

  Acyl-Protected Hydroxylamines as Spin Label Generators for EPR Brain Imaging

  摘要：

  In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.

  DOI：

  10.1021/jm0105169

文献信息

• [EN] SULFONATED NITROPHENOLS AS POLYMERIZATION INHIBITORS<br/>[FR] NITROPHÉNOLS SULFONÉS EN TANT QU'INHIBITEURS DE LA POLYMÉRISATION
  申请人：CHEMTURA CORP

  公开号：WO2006036426A1

  公开（公告）日：2006-04-06

  Disclosed herein is a method for inhibiting and retarding the premature polymerization and the polymer growth of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of at least one inhibitor that is a sulfonated nitrophenol of the formula: (I) wherein: R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, NO2, and S03H, provided that at least one of R,, R2, and R3 is NO2 and at least one of R1, R2, and R3 is SO3H. In a preferred embodiment, at least one additional inhibitor selected from the group consisting of nitroxyl compounds, nitrosoanilines, nitrophenols, amines, and mixtures thereof is also added.

  本文揭示了一种抑制和延缓乙烯基不饱和单体的聚合物的过早聚合和聚合物生长的方法，包括向所述单体中添加至少一种抑制剂，其为公式（I）的磺化硝基苯酚的有效量：其中：R1、R2和R3是独立选择自氢、烷基、NO2和S03H的群组，前提是R1、R2和R3中至少有一个是NO2，且R1、R2和R3中至少有一个是SO3H。在优选实施例中，还添加了至少一种来自亚硝基化合物、亚硝基苯胺、硝基苯酚、胺和它们的混合物的附加抑制剂。
• Blends of quinone alkide and nitroxyl compounds and polymerization inhibitors
  申请人：——

  公开号：US20040010159A1

  公开（公告）日：2004-01-15

  Disclosed herein is a method for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of: A) at least one nitroxyl compound, and B) at least one quinone alkide compound having an electron-withdrawing group at the 7-position. Additionally, a composition is disclosed that comprises: A) at least one nitroxyl compound, and B) at least one quinone alkide compound having an electron-withdrawing group at the 7-position.

  本公开涉及一种抑制乙烯基不饱和单体的过早聚合的方法，包括向所述单体中添加有效量的：A) 至少一种亚硝基化合物，和B) 在7位具有电子吸引基团的至少一种醌烯化合物。此外，还公开了一种包括：A) 至少一种亚硝基化合物，和B) 在7位具有电子吸引基团的至少一种醌烯化合物的组合物。
• MITOCHONDRIA TARGETED CATIONIC ANTI-OXIDANT COMPOUNDS FOR PREVENTION, THERAPY OR TREATMENT OF HYPER-PROLIFERATIVE DISEASE, NEOPLASIAS AND CANCERS
  申请人：Zarling David A.

  公开号：US20110059922A1

  公开（公告）日：2011-03-10

  The inventions disclosed include methods of treating cancers and related neoplasias, especially prostate cancer, with pharmaceutically acceptable salts comprising lipophilic cation moieties linked to nitroxide or linked to hydroxylamine anti-oxidant groups.

  披露的发明包括使用含有脂溶性阳离子基团与亚硝酰基或羟胺抗氧化基团相连的药用盐来治疗癌症和相关的新生物病变，特别是前列腺癌的方法。
• Inhibition of polymerization of unsaturated monomers
  申请人：——

  公开号：US20020037958A1

  公开（公告）日：2002-03-28

  Disclosed herein is a method for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of a mixture comprising: A) at least one stable hindered nitroxyl compound having the structural formula: 1 wherein R 1 and R 4 are independently selected from the group consisting of hydrogen, alkyl, and heteroatom-substituted alkyl and R 2 and R 3 are independently selected from the group consisting of alkyl and heteroatom-substituted alkyl; and X 1 and X 2 (1) are independently selected from the group consisting of halogen, cyano, COOR 7 , —S—COR 7 , —OCOR 7 , (wherein R 7 is alkyl or aryl), amido, —S—C 6 H 5 , carbonyl, alkenyl, or alkyl of 1 to 15 carbon atoms, or (2) taken together, form a ring structure with the nitrogen; and B) at least one inhibitor selected from the group consisting of ortho-quinone, ortho-hydroquinone, para-quinone, para-hydroquinone, and derivatives of the foregoing.

  本文公开了一种抑制乙烯基不饱和单体过早聚合的方法，包括向所述单体中加入有效量的混合物，该混合物包括 A) 至少一种具有结构式的稳定受阻硝基化合物： 1 其中 R 1 和 R 4 独立地选自氢、烷基、杂原子取代的烷基和 R 2 和 R 3 独立地选自由烷基和杂原子取代的烷基组成的组；以及 X 1 和 X 2 (1)独立地选自由卤素、氰基、COR 7 、-S-COR 7 、-OCOR 7 ，（其中 R 7 为烷基或芳基）、氨基、-S-C 6 H 5 1至15个碳原子的羰基、烯基或烷基，或(2)合在一起与氮形成环状结构；以及 B) 至少一种选自邻醌、邻氢醌、对苯醌、对氢醌和上述物质的衍生物的抑制剂。
• Recycle of nitroxyl-containing streams at low temperature
  申请人：——

  公开号：US20020123658A1

  公开（公告）日：2002-09-05

  An improved process for the production and purification of unsaturated monomers employing nitroxyl-containing inhibitors wherein process streams containing the inhibitor are recycled is disclosed, wherein the improvement comprises recycling said streams at a reboiler temperature no higher than about 110° C.

  本发明公开了一种采用含硝基抑制剂的不饱和单体生产和提纯的改进工艺，其中含有抑制剂的工艺流被循环利用，改进工艺包括在再沸器温度不高于约 110°C 的条件下循环利用所述工艺流。