N-(3-bromo-3-phenylpropyl)-4-methylbenzenesulfonamide | 1202798-92-2

• 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: N-(3-bromo-3-phenylpropyl)-4-methylbenzenesulfonamide
• CAS: 1202798-92-2
• 化学式: C₁₆H₁₈BrNO₂S
• 分子量: 368.294
• InChiKey: UREYGSGALLEJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-tosyl-2-phenylazetidine 在 三氟化硼乙醚 、 四丁基溴化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以98%的产率得到N-(3-bromo-3-phenylpropyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y

文献信息

• 10.1002/anie.202406485
  作者：Chen, Jinhong、Tan, Clarence、Rodrigalvarez, Jesus、Zhang, Shuai、Martin, Ruben

  DOI：10.1002/anie.202406485

  日期：——

  A site-selective bromination of C(sp3)−H bonds in unprotected aliphatic amines has been developed, achieved by tuning of the electronics properties of the proximal C−H bonds via substrate protonation. Consecutive intramolecular cyclization of alkyl bromide offered a series of N-containing heterocycles characterized by high ring strains. Moreover, the resulting C(sp3)−Br serves as a synthetic linchpin

  已开发出未受保护的脂肪胺中 C(sp 3 )−H 键的位点选择性溴化，通过底物质子化调节近端 C−H 键的电子特性来实现。烷基溴的连续分子内环化提供了一系列以高环张力为特征的含氮杂环。此外，所得的C(sp 3 )−Br作为合成关键，可以很容易地转移到C(sp 3 )−C、N、O键，从而在之前未接触过的C(sp 3 )−H位点上实现多种功能化。
• BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of <i>N</i>-Activated Aziridines and <i>N</i>-Activated Azetidines by Tetraalkylammonium Halides
  作者：Manas K. Ghorai、Amit Kumar、Deo Prakash Tiwari

  DOI：10.1021/jo902244y

  日期：2010.1.1

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.