N,N',N'',N'''-tetramethyl-1-(2,6-diethylphenylureido)-3-(2-bromophenylureido)benzene | 935750-88-2

• 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,N',N'',N'''-tetramethyl-1-(2,6-diethylphenylureido)-3-(2-bromophenylureido)benzene
• 英文别名: 1-(2-Bromophenyl)-3-[3-[[(2,6-diethylphenyl)-methylcarbamoyl]-methylamino]phenyl]-1,3-dimethylurea
• CAS: 935750-88-2
• 化学式: C₂₈H₃₃BrN₄O₂
• 分子量: 537.5
• InChiKey: QUTNLIQFKQDBIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N',N'',N'''-tetramethyl-1-(2,6-diethylphenylureido)-3-(2-bromophenylureido)benzene 、 (R)-(+)-对甲苯亚磺酸D-甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以83%的产率得到1-((3-(2-((Ss)-p-tolylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(2,6-diethylphenyl)-3-methyl)-1-methylurea
  参考文献：
  名称：

  Helix Persistence and Breakdown in Oligoureas of Metaphenylenediamine: Apparent Diastereotopicity as a Spectroscopic Marker of Helix Length in Solution

  摘要：

  Oligomeric ureas derived from m-phenylenediamine with chain lengths of up to seven urea linkages were made by iterative synthetic pathways. Three families were synthesized: 4 and 20, bearing a terminal chiral sulfinyl group; 24, bearing a terminal rotationally restricted amide group, and 30 bearing a terminal achiral bromophenyl group. The distal end of the oligomers was capped with an N-benzyl group to act as a diastereotopic probe. With a terminal sulfinyl group, the H-1 NMR signals arising from the CH2 group of the diastereotopic probe remained anisochronous even when separated from the stereogenic center by up to 24 bonds (in 20c). With a rotationally restricted amide, anisochronicity was no longer apparent beyond 17 bond lengths (in 24c). No anisochronicity was observable with a terminal bromophenyl group. We interpret these results as indicating that the oligoureas of short lengths adopt a defined helical secondary structure in solution, but that in longer oligomers the helicity breaks down and transmission of chirality in these systems is limited to about 24 bond lengths. We propose that "apparent diastereotopicity" (anisochronicity) provides a general empirical method for identifying secondary structure in solution.

  DOI：

  10.1021/ja805758v
• 作为产物：
  描述：

  、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以1.51 g的产率得到N,N',N'',N'''-tetramethyl-1-(2,6-diethylphenylureido)-3-(2-bromophenylureido)benzene
  参考文献：
  名称：

  Synthesis and Stacked Conformations of Symmetrical and Unsymmetrical Oligo-ureas of Metaphenylenediamine

  摘要：

  The addition of substituted anilines to nitro-substituted isocyanates followed by reduction generates new aniline-substituted ureas, which can be further extended in a one- or two-directional iterative manner to form oligomeric ureas based on a m-phenylenediamine monomer. Oligo-ureas with up to eight urea linkages are reported. Fully N-substituted oligo-ureas are crystalline, and the X-ray crystal structures display ring-stacked conformations. H-1 NMR studies indicate that the stacked conformation persists in solution.

  DOI：

  10.1021/jo061989w

文献信息

• Helix Persistence and Breakdown in Oligoureas of Metaphenylenediamine: Apparent Diastereotopicity as a Spectroscopic Marker of Helix Length in Solution
  作者：Jonathan Clayden、Loïc Lemiègre、Gareth A. Morris、Mark Pickworth、Timothy J. Snape、Lyn H. Jones

  DOI：10.1021/ja805758v

  日期：2008.11.12

  Oligomeric ureas derived from m-phenylenediamine with chain lengths of up to seven urea linkages were made by iterative synthetic pathways. Three families were synthesized: 4 and 20, bearing a terminal chiral sulfinyl group; 24, bearing a terminal rotationally restricted amide group, and 30 bearing a terminal achiral bromophenyl group. The distal end of the oligomers was capped with an N-benzyl group to act as a diastereotopic probe. With a terminal sulfinyl group, the H-1 NMR signals arising from the CH2 group of the diastereotopic probe remained anisochronous even when separated from the stereogenic center by up to 24 bonds (in 20c). With a rotationally restricted amide, anisochronicity was no longer apparent beyond 17 bond lengths (in 24c). No anisochronicity was observable with a terminal bromophenyl group. We interpret these results as indicating that the oligoureas of short lengths adopt a defined helical secondary structure in solution, but that in longer oligomers the helicity breaks down and transmission of chirality in these systems is limited to about 24 bond lengths. We propose that "apparent diastereotopicity" (anisochronicity) provides a general empirical method for identifying secondary structure in solution.
• Synthesis and Stacked Conformations of Symmetrical and Unsymmetrical Oligo-ureas of Metaphenylenediamine
  作者：Jonathan Clayden、Loïc Lemiègre、Madeleine Helliwell

  DOI：10.1021/jo061989w

  日期：2007.3.1

  The addition of substituted anilines to nitro-substituted isocyanates followed by reduction generates new aniline-substituted ureas, which can be further extended in a one- or two-directional iterative manner to form oligomeric ureas based on a m-phenylenediamine monomer. Oligo-ureas with up to eight urea linkages are reported. Fully N-substituted oligo-ureas are crystalline, and the X-ray crystal structures display ring-stacked conformations. H-1 NMR studies indicate that the stacked conformation persists in solution.