4-iodo-2,3,5-trimethyl-phenol | 7282-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-iodo-2,3,5-trimethyl-phenol
• 英文别名: 4-iodo-2,3,5-trimethylphenol；O-methyl-3,5-dimethyl-4-iodophenol；4-Iod-2,3,5-trimethyl-phenol；4-Iod-2,3,5-trimethylphenol
• CAS: 7282-02-2
• 化学式: C₉H₁₁IO
• 分子量: 262.09
• InChiKey: PZEFUSQDCCTMRX-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  306.6±30.0 °C(Predicted)
• 密度：
  1.650±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-iodo-2,3,5-trimethyl-phenol 在 [Rh((R,R)-DIPAMP)(COD)]BF₄ 吡啶 、 palladium diacetate 、 TEA 、 氢气 、 三(邻甲基苯基)磷 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 50.0~60.0 ℃ 、413.68 kPa 条件下， 反应 22.5h， 生成
  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：

  2,3,5-三甲基苯酚 在 碘 、 氧气 、 copper(II) nitrate 作用下， 以 水 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以91%的产率得到4-iodo-2,3,5-trimethyl-phenol
  参考文献：
  名称：

  在无有机溶剂的条件下通过有氧氧碘化选择性合成碘酚的绿色催化方法

  摘要：

  在I 2作为碘化试剂，分子氧作为氧化剂，水为溶剂的温和条件下，实现了一种高效的催化方法，用于硝酸铜（II）催化的各种苯酚的好氧氧化。该催化剂不仅对具有给电子基团或吸电子基团的酚具有高活性，而且对形成对碘取代的酚具有显着的选择性。这项研究提供了一种高原子经济性的芳族酚加碘的绿色方法。

  DOI：

  10.1016/j.catcom.2017.01.019

文献信息

• Process for producing 2,6-disubstituted tyrosine
  申请人：Monsanto Company

  公开号：US04879398A1

  公开（公告）日：1989-11-07

  A process for making 2,6-disubstituted tyrosine by the noble metal coupling of a disubstituted aromatic halide or diazonium salt with an amino-protected 2-aminoacrylic acid to form a (Z)-.beta.-(disubstituted phenyl)-.alpha.-acylaminoacrylate, and asymmetrically hydrogenating the acrylate to produce the 2,6-disubstituted tyrosine.

  通过使用贵金属催化，将二取代芳香卤化物或重氮盐与氨基保护的2-氨基丙烯酸偶联，形成(Z)-β-(二取代苯基)-α-酰氨基丙烯酸酯，然后不对称地氢化丙烯酸酯以产生2,6-二取代酪氨酸的方法。
• Gas-chromatographic identification of products formed in iodination of methyl phenols by retention indices
  作者：I. V. Gruzdev、I. M. Kuzivanov、I. G. Zenkevich、B. M. Kondratenok

  DOI：10.1134/s1070427212090108

  日期：2012.9

  Iodination reaction followed by conversion of iodine-substituted methylphenols to the corresponding trifluoroacetates was suggested for improving the sensitivity of the gas-chromatographic determination of phenol and its methyl-substituted derivatives (al isomers of mono-and diethylphenols, 2,3,5-, 2,3,6-, and 3,4,5-trimethylphenols) in aqueous media. Acylation products of iodo methylphenols (104 compounds) were identified by linear-logarithmic retention indices on a standard nonpolar polydimethylsiloxane stationary phase, and the pattern of their variation with the number and nature of substituents were characterized. A procedure for identification of methyl-substituted phenols in water in their gas-chromatographic determination with an electron-capture detector was developed.
• Synthesis of some new hindered biaryls
  作者：Harry W. Gibson、F. C. Bailey

  DOI：10.1021/jo00865a033

  日期：1976.2
• GIBSON H. W.; BAILEY F. C., J. ORG. CHEM. <JOCE-AH>, 1976, 41, NO 3, 557-560
  作者：GIBSON H. W.、 BAILEY F. C.

  DOI：——

  日期：——
• US4879398A
  申请人：——

  公开号：US4879398A

  公开（公告）日：1989-11-07