1-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-1-methyl-3-phenylureido)phenyl)-1,3-dimethylurea | 1067199-29-4

• 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: 1-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-1-methyl-3-phenylureido)phenyl)-1,3-dimethylurea
• CAS: 1067199-29-4
• 化学式: C₄₃H₄₈N₆O₄S
• 分子量: 744.958
• InChiKey: NAIPASQSEYHMGA-AXAMJWTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.24
• 重原子数：
  54.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.72
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-1-methyl-3-phenylureido)phenyl)-1,3-dimethylurea 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到1-(3-(3-(2-(tert-butylsulfonyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-1-methyl-3-phenylureido)phenyl)-1,3-dimethylurea
  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：

  1-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-3-phenylureido)phenyl)-1-methylurea 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以93%的产率得到1-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylureido)phenyl)-3-(3-(3-benzyl-1-methyl-3-phenylureido)phenyl)-1,3-dimethylurea
  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