2-bromo-N-[(4-methylphenyl)sulfonyl]-N-2-propynylpropanamide

• 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-N-[(4-methylphenyl)sulfonyl]-N-2-propynylpropanamide
• 英文别名: 2-bromo-N-(4-methylphenyl)sulfonyl-N-prop-2-ynylpropanamide
• 化学式: C₁₃H₁₄BrNO₃S
• 分子量: 344.229
• InChiKey: USYRYDSVDKIUBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-[(4-methylphenyl)sulfonyl]-N-2-propynylpropanamide 在 钾硼氢 、 Cu(tris(2-pyridylmethyl)amine)SO₄*5H₂O 作用下， 以 甲醇 为溶剂， 以80%的产率得到3-methyl-4-methyl-1-(p-toluenesulfonyl)pyrrolidin-3-en-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 、 4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 0.5h， 以53%的产率得到2-bromo-N-[(4-methylphenyl)sulfonyl]-N-2-propynylpropanamide
  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

文献信息

• 5-exo Atom transfer cyclisation onto alkynes mediated by copper(I) complexes
  作者：Andrew J Clark、Gary M Battle、Andrew Bridge

  DOI：10.1016/s0040-4039(01)00060-0

  日期：2001.3

  Multidentate amine derived copper(I) halide complexes mediate the atom transfer radical cyclisation of 1-halo-N-propargylacetamides. While cyclisation of trichloro- and dichloroacetamide derivatives leads to alpha,beta -unsaturated gamma -lactams containing the gem-dihalide functional group, monohaloacetamides give rise to either cyclised atom transfer or reduction products depending upon the solvent and catalyst used. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.