N,N'-dimethyl-N,N'-di-1-naphthylurea | 112550-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-dimethyl-N,N'-di-1-naphthylurea
• 英文别名: N,N'-dimethyl-N,N'-di-α-naphthylurea；1,3-dimethyl-1,3-di(naphthalen-1-yl)urea；N,N'-Dimethyl-N,N'-di-[1]naphthyl-harnstoff；1,3-Dimethyl-1,3-dinaphthalen-1-ylurea
• CAS: 112550-87-5
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: HXJVSTIZMZSVND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-dimethyl-N,N'-di-1-naphthylurea 在 氢化钾 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 α,α-binaphthyl anion radical potassium salt
  参考文献：
  名称：

  N,N‘-Dimethyl-N,N‘-diarylurea Anion Radicals:  An Intramolecular Reductive Elimination

  摘要：

  The one-electron reduction of tertiary N,N'-dimethyl-N,N'-diarylureas (aryl = phenyl, beta-naphthyl, alpha-naphthyl), in HMPA, results in anion radicals that undergo novel intramolecular reductive elimination reactions leading to the formation of the anion radicals of the corresponding biaryls. These results are due to face to face pi-pi stacking interactions involving the two aromatic rings in the urea systems. The overlapping p(pi)() orbitals on the ipso carbons of opposing aryl groups evolve into a sigma bond leading to the formation of the biaryl anion radical. In the case of the N,N'-dimethyl-N,N'-di-2-pyrenylurea system, there is a node in the LUMO of the number 2 carbon, and the parent anion radical remains intact.

  DOI：

  10.1021/ja0291890
• 作为产物：
  描述：

  N-ethyl-N-(naphthalen-1-yl)carbamoyl chloride 在 四(三苯基膦)钯 、 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以39%的产率得到N,N'-dimethyl-N,N'-di-1-naphthylurea
  参考文献：
  名称：

  钯催化脱羰 C-N 偶联将芳基氨基甲酰氯转化为尿素衍生物

  摘要：

  摘要 本文描述了钯催化的脱羰 C-N 偶联反应的发展，该反应在氮气氛下将芳基氨基甲酰氯转化为四取代的脲。广泛的官能团与该反应相容，并且可以以良好到高产率获得多种尿素衍生物。图形概要

  DOI：

  10.1080/00397911.2020.1793207

文献信息

• Ground-State Conformational Equilibrium and Photochemical Behavior of Syn and Anti <i>N</i>,<i>N</i><i>‘</i>-Dimethyl-<i>N</i>,<i>N</i><i>‘</i>-di-1-naphthylurea Protophanes
  作者：Todd L. Kurth、Frederick D. Lewis

  DOI：10.1021/ja034311w

  日期：2003.11.1

  The structure, spectroscopy, and photochemistry of N,N'-dimethyl-N,N'-di-1-naphthylurea have been investigated and compared to the properties of the corresponding secondary diarylurea N,N'-di-1-naphthylurea and the tertiary mono arylurea N,N,N'-trimethyl-N'-1-naphthylurea. The crystal structures and solution NMR spectra of the tertiary and secondary dinaphthylureas establish that they adopt folded

  研究了 N,N'-二甲基-N,N'-di-1-naphthylurea 的结构、光谱和光化学，并与相应的仲二芳基脲 N,N'-di-1-naphthylurea 和叔单芳基脲 N,N,N'-三甲基-N'-1-萘脲。叔二萘脲的晶体结构和溶液 NMR 谱表明它们在固态和溶液中分别采用折叠 (E,E) 和扩展 (Z,Z) 结构。在溶液中，叔 E,E-二萘脲作为顺式和反式构象的混合物存在，被约 14 kcal/mol，由变温 (1) H NMR 光谱测定。对基态势能面的计算探索表明，顺式和反式构象异构体相互转化的最低能量途径需要同时围绕氮-萘和氮-羰基单键旋转。由于萘环之间的激子相互作用，叔联萘脲表现出蓝移吸收和红移发射。二级二萘脲和单萘脲具有典型的类萘单体吸收和荧光光谱。双指数荧光衰减分配给三级联萘脲的两个构象异构体。荧光衰减时间的非线性拟合为两个构象异构体的单线态衰减提供了激活参数。衰变过程归
• Tsuruoka et al., Yuki Gosei Kagaku Kyokaishi, 1959, vol. 17, p. 144,146
  作者：Tsuruoka et al.

  DOI：——

  日期：——
• Palladium-catalyzed decarbonylative C–N coupling to convert arylcarbamoyl chlorides to urea derivatives
  作者：Aihong Fan、Jinsong Peng、Dun Zhou、Xiang Li、Chunxia Chen

  DOI：10.1080/00397911.2020.1793207

  日期：2020.10.17

  Abstract This paper describes the development of a palladium-catalyzed decarbonylative C–N coupling reaction that transforms arylcarbamoyl chlorides into tetrasubstituted ureas under a nitrogen atmosphere. A broad range of functional groups are compatible with this reaction, and diverse urea derivatives can be obtained with good to high yields. Graphical Abstract

  摘要 本文描述了钯催化的脱羰 C-N 偶联反应的发展，该反应在氮气氛下将芳基氨基甲酰氯转化为四取代的脲。广泛的官能团与该反应相容，并且可以以良好到高产率获得多种尿素衍生物。图形概要
• <i>N</i>,<i>N</i><i>‘</i>-Dimethyl-<i>N</i>,<i>N</i><i>‘</i>-diarylurea Anion Radicals:  An Intramolecular Reductive Elimination
  作者：Todd L. Kurth、Frederick D. Lewis、Chris M. Hattan、Richard C. Reiter、Cheryl D. Stevenson

  DOI：10.1021/ja0291890

  日期：2003.2.1

  The one-electron reduction of tertiary N,N'-dimethyl-N,N'-diarylureas (aryl = phenyl, beta-naphthyl, alpha-naphthyl), in HMPA, results in anion radicals that undergo novel intramolecular reductive elimination reactions leading to the formation of the anion radicals of the corresponding biaryls. These results are due to face to face pi-pi stacking interactions involving the two aromatic rings in the urea systems. The overlapping p(pi)() orbitals on the ipso carbons of opposing aryl groups evolve into a sigma bond leading to the formation of the biaryl anion radical. In the case of the N,N'-dimethyl-N,N'-di-2-pyrenylurea system, there is a node in the LUMO of the number 2 carbon, and the parent anion radical remains intact.