N-iso-propyl-α-tert-butylnitrone | 140116-62-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-iso-propyl-α-tert-butylnitrone
• 英文别名: N-Isopropyl-(2,2-dimethylpropylidene)amine N-oxide；2,2-dimethyl-N-propan-2-ylpropan-1-imine oxide
• CAS: 140116-62-7
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: RXFUEVFXFRTBQV-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-iso-propyl-α-tert-butylnitrone 在 lead dioxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.08h， 生成 2,5,5-trimethyl-3-(1-phenylethoxy)-4-phenyl-3-azahexane
  参考文献：
  名称：

  用于“活性”自由基聚合的通用烷氧基胺的开发

  摘要：

  对新型烷氧基胺的研究表明，硝基氧在介导各种乙烯基单体的“活性”或受控聚合方面发挥着关键作用。调查各种不同的烷氧基胺结构导致基于 2,2,5-trimethyl-4-phenyl-3-azahex-3-oxy, 1, 骨架的 α-氢化衍生物能够控制苯乙烯、丙烯酸酯的聚合、丙烯酰胺和丙烯腈基单体。对于每个单体组，分子量可以控制在 1000 到 200 000 amu 之间，多分散性通常为 1.05-1.15。基于上述单体的组合的嵌段和无规共聚物也可以用类似的控制来制备。与 2,2,6,6-四甲基哌啶氧基 (TEMPO) 相比，这些新系统代表了可在受控条件下聚合的单体范围的显着增加，并克服了与氮氧化合物介导的“活性”自由基程序相关的许多限制。单体选择和功能...

  DOI：

  10.1021/ja984013c
• 作为产物：
  描述：

  特戊醛 、 N-异丙基羟胺 在 magnesium sulfate 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以75%的产率得到N-iso-propyl-α-tert-butylnitrone
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8

文献信息

• Formation of cycloadducts with trans-configurated ester groups from nitrones and dimethyl maleate
  作者：Hans Günter Aurich、Gerlinde Frenzen、Markus G. Rohr

  DOI：10.1016/s0040-4020(01)90471-5

  日期：——

  there is no clue for either a non-concerted reaction course or a subsequent conversion of the cis-products to trans-product in general. Rather conversion of dimethyl maleate to dimethyl fumarate seems to be responsible for the formation of the trans-substituted cycloadducts. This conversion can be induced by small quantities of N-alkylhydroxylamine formed from slight decomposition of nitrones under the

  在1.3偶极环加成中，环状硝酮1c和非环状硝酮8a-h 12a b用马来酸二甲酯在回流的氯仿中，不仅形成了具有两个酯基的顺式构型的预期环加合物，而且还形成了具有反式构型的环加合物。该现象不仅限于氯仿，而且在极性溶剂如环己烷和正己烷中也观察到。但是，对于不确定的反应过程或随后的顺式产物向反式产物的转化，通常都没有任何线索。马来酸二甲酯向富马酸二甲酯的相反转化似乎是反式取代的环加合物形成的原因。在反应条件下，由硝酮的轻微分解形成的少量N-烷基羟胺，或由少量具有NOH部分的硝酮衍生物（如N-羟基烯胺互变异构体或硝酮二聚体）可以诱导这种转化。
• Development of a Universal Alkoxyamine for “Living” Free Radical Polymerizations
  作者：Didier Benoit、Vladimir Chaplinski、Rebecca Braslau、Craig J. Hawker

  DOI：10.1021/ja984013c

  日期：1999.4.1

  “living” or controlled polymerization of a wide range of vinyl monomers. Surveying a variety of different alkoxyamine structures led to α-hydrido derivatives based on a 2,2,5-trimethyl-4-phenyl-3-azahexane-3-oxy, 1, skeleton which were able to control the polymerization of styrene, acrylate, acrylamide, and acrylonitrile based monomers. For each monomer set, the molecular weight could be controlled from 1000

  对新型烷氧基胺的研究表明，硝基氧在介导各种乙烯基单体的“活性”或受控聚合方面发挥着关键作用。调查各种不同的烷氧基胺结构导致基于 2,2,5-trimethyl-4-phenyl-3-azahex-3-oxy, 1, 骨架的 α-氢化衍生物能够控制苯乙烯、丙烯酸酯的聚合、丙烯酰胺和丙烯腈基单体。对于每个单体组，分子量可以控制在 1000 到 200 000 amu 之间，多分散性通常为 1.05-1.15。基于上述单体的组合的嵌段和无规共聚物也可以用类似的控制来制备。与 2,2,6,6-四甲基哌啶氧基 (TEMPO) 相比，这些新系统代表了可在受控条件下聚合的单体范围的显着增加，并克服了与氮氧化合物介导的“活性”自由基程序相关的许多限制。单体选择和功能...
• Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes
  作者：Hans Günter Aurich、Michael Franzke、Hans Peter Kesselheim、Markus Rohr

  DOI：10.1016/s0040-4020(01)88127-8

  日期：——

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.