2-t-butoxy-1-cyano-1-(1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxy)ethane | 82894-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-t-butoxy-1-cyano-1-(1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxy)ethane
• 英文别名: 3-[(2-methylpropan-2-yl)oxy]-2-(1,1,3,3-tetramethylisoindol-2-yl)oxypropanenitrile
• CAS: 82894-88-0
• 化学式: C₁₉H₂₈N₂O₂
• 分子量: 316.444
• InChiKey: BRXNHYLDLWJRMS-UHFFFAOYSA-N

物化性质

• 沸点：
  415.1±55.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  45.49
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-苄基-1,1,3,3-四甲基异吲哚啉 在 palladium on activated charcoal 氢气 、 丙烯腈 作用下， 以 溶剂黄146 为溶剂， 生成 2-t-butoxy-1-cyano-1-(1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxy)ethane
  参考文献：
  名称：

  与清除剂1,1,3,3-四甲基异吲哚基-2-氧自由基反应的定量研究

  摘要：

  通过使用标题氮氧化物作为自由基清除剂的技术，发现了以前未曾观察到的对-丁氧基自由基攻击乙烯基单体的反应途径。

  DOI：

  10.1016/s0040-4039(00)87091-4

文献信息

• The Reaction of Organophosphorus Radicals With Vinyl Acetate and Acrylonitrile in the Presence of an Aminoxyl Radical Scavenger
  作者：WK Busfield、ID Grice、ID Jenkins

  DOI：10.1071/ch9950625

  日期：——

  The radical-trapping technique employing 1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxyl (1) as a radical scavenger has been used to study the reaction of diphenylphosphinoyl (2) and dimethoxyphosphinoyl (3) radicals with vinyl acetate and acrylonitrile. The phosphorus- centred radicals were generated by hydrogen abstraction from diphenylphosphine oxide and dimethyl phosphite respectively. Diphenylphosphine oxide was approximately three times as reactive as dimethyl phosphite towards hydrogen abstraction by t- butoxyl radicals and four times as reactive as tetrahydrofuran (towards abstraction of an α-hydrogen). Diphenylphosphinoyl radicals were found to be relatively nucleophilic and, in competition experiments, reacted about an order of magnitude faster with acrylonitrile than with vinyl acetate. Dimethoxyphosphinoyl radicals were rather less nucleophilic and reacted only twice as fast with acrylonitrile as they did with vinyl acetate. In the presence of excess aminoxyl (1), both diphenylphosphinoyl and dimethoxyphosphinoyl radicals were efficiently scavenged to produce stable phosphinic and phosphate esters respectively. The rate of scavenging was close to diffusion-controlled (c. 1.8×109 1. mol-1 s-1).

  以 1,1,3,3-四甲基-1,3-二氢-2H-异吲哚-2-基氧基（1）为自由基清除剂的自由基捕获技术被用于研究二苯基膦酰（2）和二甲氧基膦酰（3）自由基与醋酸乙烯酯和丙烯腈的反应。以磷为中心的自由基分别通过从二苯基氧化膦和亚磷酸二甲酯中抽取氢而生成。 二苯基氧化膦对 t-丁氧自由基析取氢的反应活性大约是亚磷酸二甲酯的三倍，是四氢呋喃（析取 α-氢）的四倍。研究发现，二苯基膦酰基具有较强的亲核性，在竞争实验中，与丙烯腈反应的速度比与醋酸乙烯反应的速度快一个数量级。 二甲氧基膦酰基的亲核性较弱，与丙烯腈反应的速度仅是与醋酸乙烯反应速度的两倍。在存在过量氨基己基（1）的情况下，二苯基膦酰和二甲氧基膦酰自由基都能被有效清除，分别生成稳定的膦酸酯和磷酸酯。清除速率接近于扩散控制（c. 1.8×109 1. mol-1 s-1）。
• Initiation Processes in Copolymerization Studied by the Nitroxide Radical-Trapping Technique: Ethyl Vinyl Ether and Acrylonitrile
  作者：W. Ken Busfield、W. Ken Busfield、Ian D. Jenkins、Ian D. Jenkins、Michael J. Monteiro、Michael J. Monteiro

  DOI：10.1071/c96016

  日期：——

  The nitroxide free-radical trapping technique has been applied to an investigation of the initiation mechanism of the copolymerization of ethyl vinyl ether and acrylonitrile initiated by t-butoxyl radicals. In addition to a range of products normally produced from reactions with individual monomers, four new trapped products each involving both monomers have been observed. These arise because the strongly electron-accepting acrylonitrile reacts so fast with the strongly nucleophilic ethyl vinyl ether radical end groups that the reaction competes successfully with radical trapping. t-Butoxyl radicals react 3-6 times faster with ethyl vinyl ether than with acrylonitrile depending on solvent, illustrating the strong electrophilic nature of the t-butoxyl radicals. Reactions carried out in non-olefinic solvents show that polarity is not a major factor in the solvent e®ect. It is more likely to be due to selective interaction of one monomer with the radical end enhancing its electrophilic nature. A similar e®ect is caused by a hydrogen-bonding solvent.

  亚硝基自由基捕获技术已被应用于 乙烯基醚和丙烯腈共聚物的引发机理进行了研究。 乙烯基醚和丙烯腈共聚物的引发机理进行了研究。除了 一系列通常由单体反应产生的产物、 还观察到四种涉及两种单体的新的受困产物。 产生这些产物的原因是强电子接受性丙烯腈与强亲核性 与强亲核乙烯基醚自由基末端基团的反应速度非常快，以至于 t-丁氧基自由基与乙基乙烯基醚自由基末端基团的反应速度是后者的 3-6 倍。 与乙烯基乙醚反应的速度是与丙烯腈反应速度的 3-6 倍。 根据溶剂的不同，t-丁氧基与乙烯基乙醚的反应速度是与丙烯腈反应速度的 3-6 倍。 叔丁氧自由基的强亲电性。在非烯烃溶剂中进行的反应表明 极性不是溶剂效应的主要因素。它更可能是 是由于一种单体与自由基末端的选择性相互作用增强了其亲电性。 其亲电性。氢键溶剂也会产生类似的效应。 溶剂。
• GRIFFITHS, P. G.;RIZZARDO, E.;SOLOMON, D. H., TETRAHEDRON LETT., 1982, 23, N 12, 1309-1312
  作者：GRIFFITHS, P. G.、RIZZARDO, E.、SOLOMON, D. H.

  DOI：——

  日期：——