3,3-dimethyl-4-(2-bromoisopropyl)-1-(p-toluenesulfonyl)pyrrolidin-2-one | 1050654-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3,3-dimethyl-4-(2-bromoisopropyl)-1-(p-toluenesulfonyl)pyrrolidin-2-one
• 英文别名: 4-(2-Bromopropan-2-yl)-3,3-dimethyl-1-(4-methylphenyl)sulfonylpyrrolidin-2-one
• CAS: 1050654-18-6
• 化学式: C₁₆H₂₂BrNO₃S
• 分子量: 388.326
• InChiKey: ZDGPXKRGCRBJGC-UHFFFAOYSA-N

物化性质

• 沸点：
  460.4±47.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-prenylpropanamide 在 偶氮二异丁腈 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到3,3-dimethyl-4-(2-bromoisopropyl)-1-(p-toluenesulfonyl)pyrrolidin-2-one
  参考文献：
  名称：

  Copper mediated atom transfer radical cyclisations with AIBN

  摘要：

  We have shown that it is possible to mediate a range of 5-exo trig and 5-exo dig atom transfer radical cyclisations of bromoacetamides using 0.1-1 mol % CuBr or CuBT2 in conjunction with 0.1-1 mol % tri(pyridin-2-ylmethyl)amine and 10 mol % AIBN. This equates to a 30-300-fold reduction in the amount of catalyst previously reported for these reactions and allows cyclisation to be carried out with the more oxidatively stable CuBr2 without the requirement of an inert atmosphere. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.016

文献信息

• Atom-Transfer Cyclization with CuSO₄/KBH₄: A Formal “Activators Generated by Electron Transfer” Process Also Applicable to Atom-Transfer Polymerization
  作者：Andrew J. Clark、Alana E. C. Collis、David J. Fox、Lauren L. Halliwell、Natalie James、Rachel K. O’Reilly、Hemal Parekh、Andrew Ross、Andrew B. Sellars、Helen Willcock、Paul Wilson

  DOI：10.1021/jo301429a

  日期：2012.8.17

  The 4-exo and 5-exo-trig atom-transfer cyclizations of 1, 8a-e, 9, 12, and 13 can be mediated with as little as 0.05 mol % of Cu(TPMA)SO4 center dot 5H(2)O in the presence of 2.5 mol % of borohydride salts in 10 min at room temperature in air. This formal "activators generated by electron transfer" (AGET) procedure utilizes a cheap and oxidatively stable copper source (CuSO4 center dot 5H(2)O) and can be carried out in environmentally benign solvents (EtOH). It is possible to alter the product distribution in the 5-endo radical-polar crossover reactions of 10a,b and 11 by tailoring the amount of borohydride. Cyclization onto alkynes 14 and 15 is also possible in only 20 min. Controlled radical polymerization of styrene, with increased rates over conventional atom-transfer radical polymerization (ATRP), can be carried out in a controlled fashion (Mn, PDI) using either CuBr or CuSO4 center dot 5H(2)O and Bu4NBH4.