4-碘-3,5-二异丙基苯酚 | 845622-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-碘-3,5-二异丙基苯酚
• 英文名称: 3,5-diisopropyl-4-iodophenol
• 英文别名: 4-Iodo-3,5-diisopropyl-phenol；4-iodo-3,5-di(propan-2-yl)phenol
• CAS: 845622-62-0
• 化学式: C₁₂H₁₇IO
• 分子量: 304.171
• InChiKey: ZUAUTJASOBMZKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-碘-3,5-二异丙基苯酚 在 [Rh((R,R)-DIPAMP)(COD)]BF₄ 吡啶 、 盐酸 、 palladium diacetate 、 TEA 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 130.0 ℃ 、413.68 kPa 条件下， 反应 49.75h， 生成 Boc-(2',6'-diisopropyltyrosine)-Pro-Phe-Phe-NH2
  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：

  3,5-双(1-甲基乙基)苯酚 在 盐酸 、 potassium iodate 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以33.7%的产率得到4-碘-3,5-二异丙基苯酚
  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

文献信息

• SUBSTITUTED PHENOL DERIVATIVES AS ANALGESICS
  申请人：THE UNIVERSITY OF LIVERPOOL

  公开号：EP1965780A2

  公开（公告）日：2008-09-10
• Propofol derivatives as analgesics
  申请人：THE UNIVERSITY OF LIVERPOOL

  公开号：EP1965780B1

  公开（公告）日：2017-03-08
• ANALGESIA
  申请人：Leuwer Martin

  公开号：US20070142477A1

  公开（公告）日：2007-06-21

  The present invention concerns compounds derived from the anaesthetic propofol that are useful as analgesics and methods of using the same. The compounds act as co-activators of strychnine-sensitive glycine receptors and may have greater activity at those glycine receptors than at GABA A .
• METHODS OF USING PROPOFOL DERIVATIVES FOR ANALGESIA
  申请人：The University of Liverpool

  公开号：US20160095823A1

  公开（公告）日：2016-04-07

  The present invention concerns compounds derived from the anaesthetic propofol that are useful as analgesics and methods of using the same. The compounds act as co-activators of strychnine-sensitive glycine receptors and may have greater activity at those glycine receptors than at GABA A .
• [EN] ANALGESIA<br/>[FR] ANALGESIE
  申请人：UNIV LIVERPOOL

  公开号：WO2007071967A2

  公开（公告）日：2007-06-28

  [EN] The present invention concerns the use of compounds derived from the anaethetic propofol that are useful as analgesics. The compounds act as activators of glycine receptors and may have greater activity at glycine receptors in the peripheral nervous system than at GABA receptors in the central nervous system.
  [FR] La présente invention concerne l'utilisation de composés dérivés de l'anesthésique propofol qui sont utiles en tant qu'analgésiques. Les composés agissent en tant qu'activateurs de récepteurs de glycine et peuvent avoir une activité plus élevée au niveau de récepteurs de glycine dans le système nerveux périphérique qu'au niveau de récepteurs de GABA dans le système nerveux central.