1,1-Dimethylethyl 2-[(2-methoxyphenyl)methylene]hydrazinecarboxylate | 179110-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-Dimethylethyl 2-[(2-methoxyphenyl)methylene]hydrazinecarboxylate
• 英文别名: tert-butyl N-[(2-methoxyphenyl)methylideneamino]carbamate
• CAS: 179110-13-5
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: GUIIVFLBUNMKKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-Dimethylethyl 2-[(2-methoxyphenyl)methylene]hydrazinecarboxylate 在 光气 、 三光气 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.84h， 生成 methyl (2-(tert-butoxycarbonyl)-1-(2-methoxybenzyl)hydrazine-1-carbonyl)-L-prolinate
  参考文献：
  名称：

  Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)

  摘要：

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.

  DOI：

  10.1021/co300015k
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 邻甲氧基苯甲醛 以 甲苯 为溶剂， 反应 0.67h， 生成 1,1-Dimethylethyl 2-[(2-methoxyphenyl)methylene]hydrazinecarboxylate
  参考文献：
  名称：

  Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)

  摘要：

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.

  DOI：

  10.1021/co300015k

文献信息

• Combinatorial Aid for Underprivileged Scaffolds: Solution and Solid-phase Strategies for a Rapid and Efficient Access To Novel Aza-diketopiperazines (Aza-DKP)
  作者：Dominique Bonnet、Jean-François Margathe、Sally Radford、Elsa Pflimlin、Stéphanie Riché、Pete Doman、Marcel Hibert、A. Ganesan

  DOI：10.1021/co300015k

  日期：2012.5.14

  An efficient solution-phase synthesis of aza-diketopiperazines (aza-DKP, triazinediones) is reported. A structurally diverse collection of c-[aza-alkylGly-Pro] derivatives and yet unreported 2,4,5-trisubstituted-1,2,4-triazine-3,6-diones has been synthesized starting from Fmoc-L-Pro-OH and various Fmoc-L-amino acids. To extend the practical value of this class of dipeptidomimetics, a general solid-phase synthesis approach amenable to library production was developed on both Wang-PS and HMBA-PS resins. The final acidic treatment of the resins in TFA/water mixture at room temperature enabled the rapid and quantitative cyclization/release highly pure triazinediones. The conformational preferences and the spatial organization of the three substituents of a representative 2,4,5-trisubstituted-1,2,4-triazine-3,6-dione were investigated by X-ray diffraction and H-1 NMR spectroscopy.