N-苄基-N-环丙基-4-甲基苯磺酰胺 | 1007719-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-N-环丙基-4-甲基苯磺酰胺
• 英文名称: N-benzyl-N-cyclopropyl-4-methylbenzenesulfonamide
• CAS: 1007719-37-0
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: DPCKTWYLBXIXQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苄基-N-环丙基-4-甲基苯磺酰胺 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到(E)-N-benzyl-4-methyl-N-(prop-1-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system

  摘要：

  Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C-C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that accesses N-heterobicyclic enones. Stoichiometric studies on a series of model rhodacyclopentanone complexes outline key structural features and provide a rationale for the efficacy of urea directing groups. A comprehensive evaluation of cycloaddition scope and a 'second generation' cationic Rh(I)-system, which provides enhanced yields and reaction rates for challenging substrates, are presented. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2015.08.052
• 作为产物：
  描述：

  N-环丙基-4-甲基苯磺酰胺 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以80%的产率得到N-苄基-N-环丙基-4-甲基苯磺酰胺
  参考文献：
  名称：

  单电子转移产生的超氧离子对N-杂环的脱氢作用

  摘要：

  在许多药物，天然产物和合成材料中都发现了含氮杂芳烃基序。尽管已经报道了几种通过相应的饱和杂环的脱氢合成这些化合物的优美方法，但是其中一些方法因反应时间长，苛刻的条件以及对催化剂的需求而难以获得。这项工作报告了一种新的N-杂环脱氢方法。具体而言，原位生成的O 2 .-充当N杂环底物的氧化剂，这些底物易受氢原子转移机制的氧化。这种方法为通向N-杂芳烃提供了一条通用的绿色路线。

  DOI：

  10.1002/chem.201705202

文献信息

• Copper-Catalyzed Amination of Primary Benzylic C−H Bonds with Primary and Secondary Sulfonamides
  作者：David A. Powell、Hope Fan

  DOI：10.1021/jo100197r

  日期：2010.4.16

  A room-temperature, copper-catalyzed amination of primary benzylic C-H bonds with primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a range of primary and secondary benzylic hydrocarbons with a diverse set of sulfonamides and is tolerant of substitution on both coupling partners. Factors which influence the selectivity of C-H functionalization between primary and secondary sites are examined.
• Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system
  作者：Megan H. Shaw、William G. Whittingham、John F. Bower

  DOI：10.1016/j.tet.2015.08.052

  日期：2016.6

  Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C-C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that accesses N-heterobicyclic enones. Stoichiometric studies on a series of model rhodacyclopentanone complexes outline key structural features and provide a rationale for the efficacy of urea directing groups. A comprehensive evaluation of cycloaddition scope and a 'second generation' cationic Rh(I)-system, which provides enhanced yields and reaction rates for challenging substrates, are presented. (C) 2015 The Authors. Published by Elsevier Ltd.
• Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
  作者：Yuan-Qiong Huang、Hong-Jian Song、Yu-Xiu Liu、Qing-Min Wang

  DOI：10.1002/chem.201705202

  日期：2018.2.9

  some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N‐heterocycles. Specifically, O2.− generated in situ acts as the oxidant for N‐heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general

  在许多药物，天然产物和合成材料中都发现了含氮杂芳烃基序。尽管已经报道了几种通过相应的饱和杂环的脱氢合成这些化合物的优美方法，但是其中一些方法因反应时间长，苛刻的条件以及对催化剂的需求而难以获得。这项工作报告了一种新的N-杂环脱氢方法。具体而言，原位生成的O 2 .-充当N杂环底物的氧化剂，这些底物易受氢原子转移机制的氧化。这种方法为通向N-杂芳烃提供了一条通用的绿色路线。