2-氯-4-(4-甲氧基苯基)苯酚 | 85972-64-1

• 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: 2-氯-4-(4-甲氧基苯基)苯酚
• 英文名称: 3-chloro-4'-methoxy-[1,1'-biphenyl]-4-ol
• 英文别名: (methoxy-4' phenyl)-4 chloro-2 phenol；2-Chloro-4-(4-methoxyphenyl)phenol
• CAS: 85972-64-1
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: VTTLALIYIIFAAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  87.4-89.8 °C
• 沸点：
  354.8±32.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴-2-氯苯酚 在 potassium phosphate 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 2-氯-4-(4-甲氧基苯基)苯酚
  参考文献：
  名称：

  Selective arylation of phenol proteted propygyl bromide via pd-catalysed Suzuki coupling reaction: synthesis, mechanistic studies by DFT calculations and Their Pharmacological Aspects"

  摘要：

  Biaryls are the potential source of synthetic drugs. The present study describes the synthesis of a series of functionalized biphenyl derivatives (3a-3g) using Pd-catalyzed Suzuki coupling reaction. The experimental results revealed the facile synthesis of biphenyl derivatives (3a-3g) with notably high yield (80-88%). Density functional theory (DFT) studies were performed by Gaussian 09 software in order to rationalize the selectivity of coupling at C-Br bond instead of C-Cl bond. In addition of synthesis. the biological activities (biofilm inhibition. hemolytic and anti-thrombolytic) of these novel compounds were investigated. These results exhibited good biofilm inhibition (5.86-65.8%), hemolytic (1.32-30.1%) and anti-thrombolytic activities (9.64-42.5%), indicating the potential use of these compounds for pharmaceutical applications.

  DOI：

  10.32383/appdr/78920

文献信息

• DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1002/anie.200905544

  日期：2010.1.18

  Palladium catalysts bearing dihydroxyterphenylphosphine ligands (such as 1) are reported for the ortho‐selective cross‐coupling of Grignard reagents and dihaloarenes. The second hydroxy group onto the terphenylphosphine ligand dramatically improved the catalytic efficiency and expanded the scope of the reaction.

  据报道，带有二羟基三苯膦配体（如1）的钯催化剂可用于格氏试剂和二卤代芳烃的邻位选择性交叉偶联。三苯基膦配体上的第二个羟基大大提高了催化效率并扩大了反应范围。
• Halogenation regioselective en serie aromatique—I
  作者：Alain Guy、Marc Lemaire、Jean-Paul Guetté

  DOI：10.1016/0040-4020(82)87011-7

  日期：1982.1

  An efficient regiospecific route for the chlorination of phenol involving hexachlorocyclohexadienones is described. The selectivity is attained by using a reagent tailored in such a way that it is able to participate in charge transfer interactions and hydrogen bonding with the substrate. This recognition between substrate (phenol) and 2, 3, 4, 4, 5, 6-hexachlorocyclohexa 2, 5-dien 1-one 1 which we

  描述了一种有效的区域特异性途径，用于氯化涉及六氯环己二酮的苯酚。通过使用以能够参与电荷转移相互作用和与底物的氢键结合的方式定制的试剂来实现选择性。底物（苯酚）和2，3，4，4，5之间的这种识别，6- hexachlorocyclohexa 2,5二烯-1-酮1我们称之为“réactif p ”允许苯酚在氯化对位置。使用2、3、4、5、6、6-六氯环己基2，4-二烯-1（我们称为“ reactif o ”）2可以在邻位进行氯化位置。这两种试剂是稳定且廉价的材料，由五氯苯酚和氯气合成。在空间控制下，用这两种试剂氯化苯甲醚，仅得到对氯衍生物。
• Highly Ortho-Selective Cross-Coupling of Dichlorobenzene Derivatives with Grignard Reagents
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1021/ol702646s

  日期：2007.12.1

  Highly ortho-selective cross-coupling of dichlorobenzene derivatives with Grignard reagents was realized using a combination of Pd-2(dba)(3) and PCy3. Use of hydroxylated terphenylphosphines further improved the reactions of dichlorophenol and dichloroaniline.
• GUY, A.;LEMAIRE, M.;GUETTE, J. -P., TETRAHEDRON, 1982, 38, N 15, 2339-2346
  作者：GUY, A.、LEMAIRE, M.、GUETTE, J. -P.

  DOI：——

  日期：——
• Selective arylation of phenol proteted propygyl bromide via pd-catalysed Suzuki coupling reaction: synthesis, mechanistic studies by DFT calculations and Their Pharmacological Aspects"
  作者：hira farooq、nasir rasool、Muhammad Ansari、komal rizwan、tariq mahmood、hira israr、Khurshid Ayub、tahir rasheed、Seema Zareen、muhammad Akhtar、sarosh iqbal

  DOI：10.32383/appdr/78920

  日期：2018.8.31

  Biaryls are the potential source of synthetic drugs. The present study describes the synthesis of a series of functionalized biphenyl derivatives (3a-3g) using Pd-catalyzed Suzuki coupling reaction. The experimental results revealed the facile synthesis of biphenyl derivatives (3a-3g) with notably high yield (80-88%). Density functional theory (DFT) studies were performed by Gaussian 09 software in order to rationalize the selectivity of coupling at C-Br bond instead of C-Cl bond. In addition of synthesis. the biological activities (biofilm inhibition. hemolytic and anti-thrombolytic) of these novel compounds were investigated. These results exhibited good biofilm inhibition (5.86-65.8%), hemolytic (1.32-30.1%) and anti-thrombolytic activities (9.64-42.5%), indicating the potential use of these compounds for pharmaceutical applications.