4-[2'-(羟甲基)苯基]苯甲醚 | 110391-98-5

• 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-[2'-(羟甲基)苯基]苯甲醚
• 英文名称: (4'-methoxybiphenyl-2-yl)methanol
• 英文别名: [2-(4-Methoxyphenyl)phenyl]methanol
• CAS: 110391-98-5
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: WTLFXGAXHUFUDB-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C(Solv: toluene (108-88-3); hexane (110-54-3))
• 沸点：
  387.8±35.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 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：

  4-[2'-(羟甲基)苯基]苯甲醚 在 phosphorus pentoxide 、 sodium hydride 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 5.33h， 生成 5-(4-Methoxy-phenyl)-1,4-dihydro-2H-isoquinoline-3,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  A novel series of selective, non-peptide inhibitors of angiotensin II binding to the AT2 site

  摘要：

  The availability of peptide and non-peptide Ang II receptor antagonists has permitted the study of Ang II receptor heterogeneity. It is now widely recognized that there are at least two distinct Ang II receptor subtypes. AT(1) receptors are selective in their recognition of agents such as losartan, DuP 532, L-158,809, SK&F108566, and similar non-peptides. To date, all of the well-known actions of Ang II in mammals are blocked by the AT(1) selective antagonists such as losartan and are thus designated as being mediated by the AT(1) receptor. Although there have been reports of functional activity mediated through AT(2) sites, the pharmacological role for the AT(2) receptor has not yet been elucidated. Herein, we report the chemistry and SAR on a novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids which have selective affinity for AT(2) receptors. The most potent of which (19) has an IC50 Of 30 nM for the AT(2) receptor in the rat adrenal radioligand binding assay.

  DOI：

  10.1021/jm00077a001
• 作为产物：
  描述：

  2-(4'-methoxyphenyl)benzyl bromide 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 以90%的产率得到4-[2'-(羟甲基)苯基]苯甲醚
  参考文献：
  名称：

  联芳系统光生醌甲基化物的溶剂分解和闭环

  摘要：

  各种联芳基醌甲基化物已经从联芳基前体 4??6 和 8、10 和 11 以一系列效率光生，它们都具有交替的羟基和羟甲基取代基。

  DOI：

  10.1139/v05-138

文献信息

• Water-soluble palladacycles containing hydroxymethyl groups: synthesis, crystal structures and use as catalysts for amination and Suzuki coupling of reactions
  作者：Xin Han、Hong-Mei Li、Chen Xu、Zhi-Qiang Xiao、Zhi-Qiang Wang、Wei-Jun Fu、Xin-Qi Hao、Mao-Ping Song

  DOI：10.1007/s11243-016-0036-5

  日期：2016.5

  2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos)]-palladacycles containing hydroxymethyl groups 2–3 were prepared by cyclopalladation and chloride bridge-splitting reactions. The complexes were characterized by elemental analysis, ESI–MS and NMR. In addition, single-crystal X-ray analysis reveals that they have one-dimensional lamellar structures involving intermolecular hydrogen bonds and π–π interactions

  通过环钯化和氯桥分裂反应制备了两种水溶性单膦 [PPh3 和 2-二环己基膦基-2',6'-二甲氧基联苯 (Sphos)]-含羟甲基 2-3 的钯环。通过元素分析、ESI-MS 和核磁共振对配合物进行表征。此外，单晶X射线分析表明它们具有涉及分子间氢键和π-π相互作用的一维层状结构。研究了使用这些钯环作为芳基氯在水中胺化和 Suzuki 偶联的催化剂。发现配合物 3 对于这些偶联反应非常有效。此外，它还成功地用于（羟甲基）苯基硼酸的 Suzuki 偶联，以合成取代的 2-N-杂环联芳甲醇。
• Pd-Mediated C-C and C-S Bond Formation on Solid Support: A Scope and Limitations Study
  作者：Sebastian Wendeborn、Sabine Berteina、Wolfgang K.-D. Brill、Alain De Mesmaeker

  DOI：10.1055/s-1998-22661

  日期：1998.6

  The scope and limitations of Pd(0)-mediated coupling reactions between aromatic halides linked to a polystyrene resin and boronic acid derivatives (Suzuki coupling), aromatic and vinylic tin compounds (Stille coupling), as well as thiols are reported. For all reactions, conditions were optimized and evaluated with various reagents. In many cases, upon cleavage from the solid support, products were obtained in excellent yields. In most cases, the optimized reaction conditions are superior to those previously reported in the literature.

  本文报道了零价钯催化的芳基卤代物与聚苯乙烯树脂相连的配体、硼酸衍生物（铃木偶联反应）、芳基和乙烯基锡化合物（斯蒂尔偶联反应）以及硫醇之间的偶联反应的范围和局限性。针对所有反应，经过优化条件并使用不同试剂进行评估。在许多情况下，从固相载体上切割下来的产物收率极佳。大多数情况下，经过优化的反应条件优于先前文献报道的条件。
• Gold-Catalyzed 6-<i>Exo</i>-<i>Dig</i>Cycloisomerization: A Versatile Approach to Functionalized Phenanthrenes
  作者：Chao Shu、Long Li、Cheng-Bin Chen、Hong-Cheng Shen、Long-Wu Ye

  DOI：10.1002/asia.201400034

  日期：2014.6

  A novel gold‐catalyzed 6‐exo‐dig cycloisomerization of o‐propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope.

  已经开发了一种新型的金催化的邻炔丙基联芳基的6- exo - dig环异构化方法，该方法可以方便地获得官能化的菲，而且收率大体上很高。该方法的显着特征是易于获得的起始原料，温和的反应条件和广泛的底物范围。
• Selective acetylation of primary alcohols by ethyl acetate
  作者：Raju Singha、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2016.10.088

  日期：2016.11

  A KOtBu and ethyl acetate mediated efficient methodology has been developed for the acetylation of primary and secondary alcohols where ethyl acetate is the source of acetyl group. The reaction is fast, mild, efficient, and highly selective towards the primary alcohols.

  已经开发了用于叔和仲醇的乙酰化的KO t Bu和乙酸乙酯介导的有效方法，其中乙酸乙酯是乙酰基的来源。该反应对伯醇快速，温和，有效且高度选择性。
• Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates
  作者：Lutz Ackermann、Anant R. Kapdi、Sabine Fenner、Christoph Kornhaaß、Carola Schulzke

  DOI：10.1002/chem.201002386

  日期：2011.3.1

  Palladium complexes of representative heteroatom‐substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X‐ray crystal structure analysis. Importantly, these well‐defined complexes served as highly efficient catalysts for Kumada–Corriu cross‐coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air‐stable catalyst derived

  代表的钯络合物ħ etero一汤姆取代小号econdary p hoSPhine ø西德（HASPO）preligands合成并充分表征，包括X射线晶体结构分析。重要的是，这些定义明确的络合物可作为Kumada-Corriu芳基，烯基乃至杂芳基甲苯磺酸酯交叉偶联反应的高效催化剂。特别是，由廉价的PinP（O）H衍生的空气稳定型催化剂显示出极高的催化效力，这导致在极低的反应条件下，在足够宽泛的反应条件下，低催化剂负载下的交叉偶联。