(E)-N-benzyl-4-methyl-N-(prop-1-en-1-yl)benzenesulfonamide | 700336-74-9

• 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: (E)-N-benzyl-4-methyl-N-(prop-1-en-1-yl)benzenesulfonamide
• 英文别名: N-benzyl-4-methyl-N-[(E)-prop-1-enyl]benzenesulfonamide
• CAS: 700336-74-9
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: KQUDHKWHPDWGPD-QLKAYGNNSA-N

物化性质

• 沸点：
  444.3±48.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-N-benzyl-4-methyl-N-(prop-1-en-1-yl)benzenesulfonamide 、 儿萘酚硼烷 在 Rh(H)(PEt₃)₃ 作用下， 以 氘代氯仿 为溶剂， 反应 5.0h， 生成 N-(3-Benzo[1,3,2]dioxaborol-2-yl-propyl)-N-benzyl-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Catalyzed hydroboration of allyl sulfonamides

  摘要：

  The hydroboration of allyl sulfonamides (4-H3CC6H4SO2NRCH2CH=CH2: R = H, 1; Ph, 2; Bz, 3) with catecholborane (HBcat) using different rhodium catalysts has been examined using multinuclear NMR spectroscopy. Reactions give complex product distributions, regardless of the choice of catalyst, arising from a competing isomerization reaction. This isomerization reaction can be used with N-substituted allyl sulfonamides 2 and 3 to give the corresponding enamines (4-H3CC6H4SO2CH=CH2CH3), which in turn react with HBcat to give regioselective formation of one isomer (4-H3CC6H4SO2NRCH2CH2(Bcat)CH3). (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00260-2
• 作为产物：
  描述：

  N-烯丙基-N-苄基-4-甲基苯磺酰胺 在 [Pd(μ-I)(Cy₂PtBu)]₂ 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到(E)-N-benzyl-4-methyl-N-(prop-1-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  下一代空气稳定的钯（I）二聚体可实现空气中的烯烃迁移和选择性CC耦合。

  摘要：

  我们报告了一种新的空气稳定的Pd I二聚体[Pd（μI）（PCy 2 t Bu）] 2，它在存在多个官能团且具有完全耐受性的情况下触发E-选择性烯烃向酰胺和苯乙烯衍生物的迁移空气 同一二聚体还可以在室温下以模块化和三重选择性的方式在聚（假）卤代芳烃中以芳族C-Br，C-OTf / OF和C-Cl键的形式快速触发C-C偶联（烷基化和芳基化）在具有邻位C-OTf的取代基的底物上显示出比以前的Pd I二聚体更好的活性。

  DOI：

  10.1002/anie.202009115

文献信息

• Ligand‐Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
  作者：Mojtaba Hajiloo Shayegan、Zhong‐Yuan Li、Xin Cui

  DOI：10.1002/chem.202103402

  日期：2022.1.3

  A palladium-catalyzed, ligand controlled regiodivergent semireduction of allenamides has been developed. This phosphine ligand-switched semireduction system has enabled an easy access to a broad scope of allylic and vinylic amides by using a single palladium catalyst. The excellent regio- and stereoselectivities of the divergent processes were achieved by the employment of monodentate Xphos and bidentate

  已经开发了钯催化的、配体控制的烯丙酰胺的区域发散半还原。这种膦配体转换的半还原系统可以通过使用单一钯催化剂轻松获得广泛的烯丙酰胺和乙烯基酰胺。通过使用单齿 Xphos 和双齿 BINAP 配体（参见方案），可以实现不同过程的出色区域选择性和立体选择性。
• A new highly chemoselective isomerization of allylamides
  作者：Benjamin Neugnot、Jean-Christophe Cintrat、Bernard Rousseau

  DOI：10.1016/j.tet.2004.03.004

  日期：2004.4

  This work describes the first iridium-catalyzed isomerization of N-allylamides into enamides. This strategy allows the chemoselective preparation of (E)-N-(1-propenyl)-enamides and can be applied for the selective deprotection of N-allylamides. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• A Next‐Generation Air‐Stable Palladium(I) Dimer Enables Olefin Migration and Selective C−C Coupling in Air
  作者：Gourab Kundu、Theresa Sperger、Kari Rissanen、Franziska Schoenebeck

  DOI：10.1002/anie.202009115

  日期：2020.12

  We report a new air‐stable PdI dimer, [Pd(μ‐I)(PCy2tBu)]2, which triggers E‐selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C−C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C−Br, C−OTf/OFs, and

  我们报告了一种新的空气稳定的Pd I二聚体[Pd（μI）（PCy 2 t Bu）] 2，它在存在多个官能团且具有完全耐受性的情况下触发E-选择性烯烃向酰胺和苯乙烯衍生物的迁移空气 同一二聚体还可以在室温下以模块化和三重选择性的方式在聚（假）卤代芳烃中以芳族C-Br，C-OTf / OF和C-Cl键的形式快速触发C-C偶联（烷基化和芳基化）在具有邻位C-OTf的取代基的底物上显示出比以前的Pd I二聚体更好的活性。
• Catalyzed hydroboration of allyl sulfonamides
  作者：Michael G. Hamilton、Catrin E. Hughes、Alison M. Irving、Christopher M. Vogels、Stephen A. Westcott

  DOI：10.1016/s0022-328x(03)00260-2

  日期：2003.8

  The hydroboration of allyl sulfonamides (4-H3CC6H4SO2NRCH2CH=CH2: R = H, 1; Ph, 2; Bz, 3) with catecholborane (HBcat) using different rhodium catalysts has been examined using multinuclear NMR spectroscopy. Reactions give complex product distributions, regardless of the choice of catalyst, arising from a competing isomerization reaction. This isomerization reaction can be used with N-substituted allyl sulfonamides 2 and 3 to give the corresponding enamines (4-H3CC6H4SO2CH=CH2CH3), which in turn react with HBcat to give regioselective formation of one isomer (4-H3CC6H4SO2NRCH2CH2(Bcat)CH3). (C) 2003 Elsevier Science B.V. All rights reserved.