4-iodo-3-isopropyl-5-methylphenol acetate | 845622-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-iodo-3-isopropyl-5-methylphenol acetate
• 英文别名: (4-Iodo-3-methyl-5-propan-2-ylphenyl) acetate
• CAS: 845622-65-3
• 化学式: C₁₂H₁₅IO₂
• 分子量: 318.154
• InChiKey: BABMASSKWGLKFE-UHFFFAOYSA-N

物化性质

• 沸点：
  310.8±42.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodo-3-isopropyl-5-methylphenol acetate 在 [Rh((R,R)-DIPAMP)(COD)]BF₄ 盐酸 、 palladium diacetate 、 TEA 、 氢气 、 三(邻甲基苯基)磷 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 60.0 ℃ 、413.68 kPa 条件下， 反应 29.25h， 生成 (2S)-3-(4-hydroxy-2-methyl-6-propan-2-ylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  Development of Potent μ-Opioid Receptor Ligands Using Unique Tyrosine Analogues of Endomorphin-2

  摘要：

  Six analogues of tyrosine, which contained alkyl groups at positions 2', 3', and 6', either singly or in combination on the tyramine ring, were investigated for their effect on the opioid activity of [Xaa(1)]endomorphin-2 (EM-2). The opioid analogues displayed the following characteristics: (i) high mu-opioid receptor affinity [K-i(mu) = 0.063-2.29 nM] with selectivity [K-i(delta)/Ki(mu)] ranging from 46 to 5347; (ii) potent functional mu-opioid agonism [GPI assay (IC50 = 0.623-0.924 nM)1 and with a correlation between delta-opioid receptor affinities and functional bioactivity using MVD; (iii) intracerebroventricular administration of [Dmt(1)]- (14) and [Det(1)]EM-2 (10) produced a dose-response antinociception in mice, with the former analogue more active than the latter; and (iv) a marked shift occurred from the trans-orientation at the Tyr(1)-Pro(2) bond to a cis-conformer compared to that observed previously with [Dmt(1)]EM-2 (14) (Okada et al. Bioorg. Med. Chem. 2003, 11, 1983-1984) except [Mmt(1)]EM-2 (7). The active profile of the [Xaa(1)]EM-2 analogues indicated that significant modifications on the tyramine ring are possible while high biological activity is maintained.

  DOI：

  10.1021/jm049384k
• 作为产物：
  描述：

  5-异丙基-3-甲酚 、 乙酸酐 在 盐酸 、 potassium iodate 、 potassium iodide 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-isopropyl-5-methylphenol acetate 、 4-iodo-3-isopropyl-5-methylphenol acetate
  参考文献：
  名称：

  Development of Potent μ-Opioid Receptor Ligands Using Unique Tyrosine Analogues of Endomorphin-2

  摘要：

  Six analogues of tyrosine, which contained alkyl groups at positions 2', 3', and 6', either singly or in combination on the tyramine ring, were investigated for their effect on the opioid activity of [Xaa(1)]endomorphin-2 (EM-2). The opioid analogues displayed the following characteristics: (i) high mu-opioid receptor affinity [K-i(mu) = 0.063-2.29 nM] with selectivity [K-i(delta)/Ki(mu)] ranging from 46 to 5347; (ii) potent functional mu-opioid agonism [GPI assay (IC50 = 0.623-0.924 nM)1 and with a correlation between delta-opioid receptor affinities and functional bioactivity using MVD; (iii) intracerebroventricular administration of [Dmt(1)]- (14) and [Det(1)]EM-2 (10) produced a dose-response antinociception in mice, with the former analogue more active than the latter; and (iv) a marked shift occurred from the trans-orientation at the Tyr(1)-Pro(2) bond to a cis-conformer compared to that observed previously with [Dmt(1)]EM-2 (14) (Okada et al. Bioorg. Med. Chem. 2003, 11, 1983-1984) except [Mmt(1)]EM-2 (7). The active profile of the [Xaa(1)]EM-2 analogues indicated that significant modifications on the tyramine ring are possible while high biological activity is maintained.

  DOI：

  10.1021/jm049384k