2-t-butoxy-1-acethoxy-1-(1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxy)ethane | 82894-91-5

• 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-acethoxy-1-(1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxy)ethane
• 英文别名: [2-[(2-methylpropan-2-yl)oxy]-1-(1,1,3,3-tetramethylisoindol-2-yl)oxyethyl] acetate
• CAS: 82894-91-5
• 化学式: C₂₀H₃₁NO₄
• 分子量: 349.47
• InChiKey: JIVUNVUQINAISU-UHFFFAOYSA-N

物化性质

• 沸点：
  423.1±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxoyl radical 在 二-叔-丁基过氧草酸酯 作用下， 以65.3%的产率得到2-t-butoxy-1-acethoxy-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）。