3-methoxy-4'-methylbiphenyl-4-ol | 58005-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methoxy-4'-methylbiphenyl-4-ol
• 英文别名: 2-Methoxy-4-(4-methylphenyl)phenol
• CAS: 58005-51-9
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: JEFCVPVCZSUHHW-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  338.3±27.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-4'-methylbiphenyl-4-ol 在 palladium diacetate 吡啶 、 potassium fluoride 、 三溴化硼 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.66h， 生成 [5-(4-methylphenyl)-2-phenylphenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Repetitive Two-step Method for Oligoarene Synthesis through Rapid Cross-coupling of Hydroxyphenylboronic Acids and Anhydrides

  摘要：

  在钯催化的交叉偶联步骤中使用了羟基苯硼酸或酸酐，开发出了一种用于合成低聚烯烃的两步式 Suzuki-Miyaura 偶联-三氟化反应程序。

  DOI：

  10.1246/cl.2006.164
• 作为产物：
  描述：

  4-羟基-3-甲氧硼酸频哪醇酯 、 对苄基三氟甲磺酸 在 palladium diacetate lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以98%的产率得到3-methoxy-4'-methylbiphenyl-4-ol
  参考文献：
  名称：

  Synthetic method for multifunctionalized oligoarenes using pinacol esters of hydroxyphenylboronic acids

  摘要：

  利用羟基苯硼酸频哪醇酯的快速 Suzukii-Miyaura 偶联和随后羟基的三重化，开发了一种多功能低聚烯烃的合成方法。

  DOI：

  10.1039/b603574d

文献信息

• Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents
  作者：Maddali L.N. Rao、Suresh Meka

  DOI：10.1016/j.tetlet.2019.151512

  日期：2020.2

  An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.

  描述了通过未保护的碘代苯酚与三芳基铋试剂的Pd催化的交叉偶联来无保护地合成不对称羟基联芳基的有效方案。提出的协议表现出良好的羟基联芳基的高收率。
• Negishi coupling strategy of a repetitive two-step method for oligoarene synthesis
  作者：Haruka Shimizu、Kei Manabe

  DOI：10.1016/j.tetlet.2006.06.048

  日期：2006.8

  repetitive two-step method for oligoarene synthesis, based on Negishi cross-coupling of zinciophenoxides or zinciopyridinoxides with aryl triflates and subsequent triflation of the hydroxy group, was developed. Reaction conditions were optimized for the preparation of the arylzinc compounds and the palladium-catalyzed cross-coupling step.

  开发了一种新颖的重复性两步法合成低聚芳烃的方法，该方法基于Negishi将氧化锌苯酚或氧化锌吡啶氧化物与芳基三氟甲磺酸酯交叉偶联，然后对羟基进行三氟甲磺酸酯化。优化了反应条件以制备芳基锌化合物和钯催化的交叉偶联步骤。
• Efficient access to triphenylene derivatives via carbamate-directed bay-region selective arylation of biphenol derivatives and Scholl cyclization
  作者：Chuane Guo、Yunfeng Liu、Yang Liu、Hongbin Zhang、Dan Yi、Shuo Wang、Bi-Qin Wang、Shi-Kai Xiang、Yingbo Shi

  DOI：10.1016/j.tet.2024.133985

  日期：2024.5

  for carbamate-directed -C-H bond arylation of biphenyl derivatives employing diaryliodonium salts as the arylation agents was explored. Consequently, the Scholl reaction was utilized to cyclize the product, yielding 21 varieties of multifunctional triphenylene derivatives. The maximum yield achieved through this two-step process was 94 %, offering an efficient synthesis route for the production of multi-substituted

  探索了一种使用二芳基碘鎓盐作为芳基化剂的氨基甲酸酯导向的联苯衍生物-C-H键芳基化的新方法。因此，利用Scholl反应将产物环化，得到21种多官能苯并菲衍生物。通过该两步工艺实现的最大产率为 94%，为生产多取代苯并菲衍生物提供了一条有效的合成路线。
• An expeditious aqueous Suzuki–Miyaura method for the arylation of bromophenols
  作者：Joel S. Freundlich、Howard E. Landis

  DOI：10.1016/j.tetlet.2006.04.027

  日期：2006.6

  The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with,regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the C-aryl-Br bond versus the C-aryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent. (c) 2006 Elsevier Ltd. All rights reserved.
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：ASTRAZENECA AB

  公开号：WO2004024060A2

  公开（公告）日：2004-03-25

  The invention provides compounds of formula, in which X, Y, R1, G1 and G2 have the meanings defined in the specification; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.