2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-cinnamylpropanamide | 1393608-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-cinnamylpropanamide
• CAS: 1393608-08-6
• 化学式: C₂₀H₂₂BrNO₃S
• 分子量: 436.37
• InChiKey: XWHKIMFAXXGVFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-cinnamylpropanamide 在 钾硼氢 、 Cu(tris(2-pyridylmethyl)amine)SO₄*5H₂O 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3,3-dimethyl-4-(bromo(phenyl)methyl)-1-(p-toluenesulfonyl)pyrrolidin-2-one 、 3,3-dimethyl-4-(bromo(phenyl)methyl)-1-(p-toluenesulfonyl)pyrrolidin-2-one
  参考文献：
  名称：

  Atom-Transfer Cyclization with CuSO₄/KBH₄: A Formal “Activators Generated by Electron Transfer” Process Also Applicable to Atom-Transfer Polymerization

  摘要：

  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.

  DOI：

  10.1021/jo301429a
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 N-cinnamyl-4-methylbenzenesulfonamide 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 0.5h， 以1.32 g的产率得到2-bromo-2-methyl-N-[(4-methylphenyl)sulfonyl]-N-2-cinnamylpropanamide
  参考文献：
  名称：

  Atom-Transfer Cyclization with CuSO₄/KBH₄: A Formal “Activators Generated by Electron Transfer” Process Also Applicable to Atom-Transfer Polymerization

  摘要：

  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.

  DOI：

  10.1021/jo301429a