3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid | 910132-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid
• 英文别名: 3-(4-carbamoyl-2,6-dimethylphenyl)propanoic acid
• CAS: 910132-88-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: QWWQQDIAAYRICW-UHFFFAOYSA-N

物化性质

• 沸点：
  361.9±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid 、 H-c[D-Cys-Gly-Phe(p-NO2)-D-Cys]NH2*CF3CO2H 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4S,7S,13S)-13-[3-(4-carbamoyl-2,6-dimethylphenyl)propanoylamino]-7-[(4-nitrophenyl)methyl]-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxamide
  参考文献：
  名称：

  Replacement of the N-terminal Tyrosine Residue in Opioid Peptides with 3-(2,6-Dimethyl-4-carbamoylphenyl)propanoic Acid (Dcp) Results in Novel Opioid Antagonists

  摘要：

  3-(2,6-Dimethyl-4-carbamoylphenyl) propanoic acid (Dcp), a 2',6'-dimethyltyrosine analogue containing a carbamoyl group in place of the hydroxyl function and lacking the amino group, was synthesized. The replacement of Tyr(1) in an enkephalin analogue and in dynorphin A(1-11)-NH2 with Dcp resulted in the first opioid peptide-derived antagonists that do not contain a phenolic hydroxyl group at the 1-position residue. The cyclic peptide Dcp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys] NH2 represents a novel, potent mu opioid antagonist.

  DOI：

  10.1021/jm060369k
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 palladium on activated charcoal 、 三乙胺 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium iodate 、 copper(l) iodide 、 正丁基锂 、 硫酸 、 氨 、 氢气 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， -78.0~110.0 ℃ 、413.68 kPa 条件下， 反应 94.16h， 生成 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid
  参考文献：
  名称：

  Replacement of the N-terminal Tyrosine Residue in Opioid Peptides with 3-(2,6-Dimethyl-4-carbamoylphenyl)propanoic Acid (Dcp) Results in Novel Opioid Antagonists

  摘要：

  3-(2,6-Dimethyl-4-carbamoylphenyl) propanoic acid (Dcp), a 2',6'-dimethyltyrosine analogue containing a carbamoyl group in place of the hydroxyl function and lacking the amino group, was synthesized. The replacement of Tyr(1) in an enkephalin analogue and in dynorphin A(1-11)-NH2 with Dcp resulted in the first opioid peptide-derived antagonists that do not contain a phenolic hydroxyl group at the 1-position residue. The cyclic peptide Dcp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys] NH2 represents a novel, potent mu opioid antagonist.

  DOI：

  10.1021/jm060369k

文献信息

• Replacement of the <i>N</i>-terminal Tyrosine Residue in Opioid Peptides with 3-(2,6-Dimethyl-4-carbamoylphenyl)propanoic Acid (Dcp) Results in Novel Opioid Antagonists
  作者：Yixin Lu、Tze Keong Lum、Yoon Wui Leow Augustine、Grazyna Weltrowska、Thi M.-D. Nguyen、Carole Lemieux、Nga N. Chung、Peter W. Schiller

  DOI：10.1021/jm060369k

  日期：2006.8.1

  3-(2,6-Dimethyl-4-carbamoylphenyl) propanoic acid (Dcp), a 2',6'-dimethyltyrosine analogue containing a carbamoyl group in place of the hydroxyl function and lacking the amino group, was synthesized. The replacement of Tyr(1) in an enkephalin analogue and in dynorphin A(1-11)-NH2 with Dcp resulted in the first opioid peptide-derived antagonists that do not contain a phenolic hydroxyl group at the 1-position residue. The cyclic peptide Dcp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys] NH2 represents a novel, potent mu opioid antagonist.