tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate | 910132-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate
• 英文别名: tert-butyl (E)-3-(4-carbamoyl-2,6-dimethylphenyl)prop-2-enoate
• CAS: 910132-86-4
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: CQWMLDNRHFBGIS-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 60.0 ℃ 、413.68 kPa 条件下， 反应 2.0h， 以98%的产率得到tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate
  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 三乙胺 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium iodate 、 copper(l) iodide 、 正丁基锂 、 硫酸 、 氨 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.16h， 生成 tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate
  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.