4-(4-甲氧基苄氧基)苯酚 | 77151-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(4-甲氧基苄氧基)苯酚
• 英文名称: Hydroquinone 4-methoxybenzylether
• 英文别名: O-(4-methoxybenzyl)hydroquinone；4-((4-methoxybenzyl)oxy)phenol；4-(4-methoxybenzyloxy)phenol；4-[(4-methoxyphenyl)methoxy]phenol
• CAS: 77151-89-4
• 化学式: C₁₄H₁₄O₃
• mdl: MFCD11181765
• 分子量: 230.263
• InChiKey: WVKLZNGPADNHRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-甲氧基苄氧基)苯酚 在 碘苯二乙酸 、 甘氨酸乙酯盐酸盐 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 生成 4-(4-甲氧基苄氧基)苯胺 、 甲氧苯胺
  参考文献：
  名称：

  由苯酚直接合成苯胺和亚硝基苯†

  摘要：

  已经使用ipso-氧化性芳族取代（i S O Ar）方法开发了一种从苯酚一锅合成苯胺和亚硝基苯的方法。在温和且不含金属的条件下，可以以高收率获得产品。还研究了离去基团对通过混合的醌酮单缩酮进行的反应的影响，并建立了预测模型。

  DOI：

  10.1039/c6ob00073h
• 作为产物：
  描述：

  4-甲氧基苄醇 在 氯化亚砜 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 5.0h， 生成 4-(4-甲氧基苄氧基)苯酚
  参考文献：
  名称：

  由苯酚直接合成苯胺和亚硝基苯†

  摘要：

  已经使用ipso-氧化性芳族取代（i S O Ar）方法开发了一种从苯酚一锅合成苯胺和亚硝基苯的方法。在温和且不含金属的条件下，可以以高收率获得产品。还研究了离去基团对通过混合的醌酮单缩酮进行的反应的影响，并建立了预测模型。

  DOI：

  10.1039/c6ob00073h

文献信息

• Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including <i>p</i>-methoxybenzyl ethers of alcohols and phenols
  作者：Kamlesh V. Katkar、Sachin D. Veer、Krishnacharya G. Akamanchi

  DOI：10.1080/00397911.2016.1230218

  日期：2016.12.1

  ABSTRACT Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions. GRAPHICAL ABSTRACT

  摘要 硫酸化钨酸盐被发现是一种有效的多相和可重复使用的催化剂，用于在温和的反应条件下羟基活化介导的苄醚制备，包括各种醇和酚的对甲氧基苄醚。图形概要
• Pd/C-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison.
  作者：Hironao Sajiki、Kosaku Hirota

  DOI：10.1248/cpb.51.320

  日期：——

  Employment of a Pd/C–pyridine combination as a catalyst is a very useful method for the selective removal (hydrogenolysis) of phenolic O-benzyl, N-Cbz and benzyl ester protective groups and for the selective hydrogenation of nitro and olefin functions of phenol derivatives protected with the MPM group. These discriminatory results are apparently attributable to the effect of pyridine. The MPM group could be extensively applied to chemoselective hydrogenation as a protective group for phenolic hydroxyl functions.

  使用Pd/C-吡啶组合作为催化剂是一种非常有用的方法，用于选择性地去除（氢解）酚类化合物的O-苄基、N-Cbz和苄基酯保护基团，以及选择性地氢化带有MPM保护基团的酚类衍生物中的硝基和烯烃功能团。这些差异性结果显然归因于吡啶的作用。MPM基团可广泛应用于作为酚羟基功能团的选择性氢化保护基。
• Chemoselective inhibition of the hydrogenolysis of the MPM protective group for phenolic hydroxy functions using a catalyst
  作者：Hironao Sajiki、Hiroko Kuno、Kosaku Hirota

  DOI：10.1016/s0040-4039(96)02309-x

  日期：1997.1

  A convenient method for the selective hydrogenation of phenolic benzyl ether, Cbz, benzyl ester, nitro and olefin functions distinguishing from the MPM (4-methoxybenzyl) protective group for the phenolic hydroxy groups was accomplished by the addition of pyridine to the reduction system.

  通过将吡啶加到还原体系中来实现选择性氢化酚苄基醚，Cbz，苄基酯，硝基和烯烃官能团的简便方法，该官能团不同于酚羟基的MPM（4-甲氧基苄基）保护基。
• Citterio, Attilio, Gazzetta Chimica Italiana, 1980, vol. 110, # 4, p. 253 - 258
  作者：Citterio, Attilio

  DOI：——

  日期：——
• Mechanism of the Gibbs Reaction. 3. Indophenol Formation via Radical Electrophilic Aromatic Substitution (SREAr) on Phenols
  作者：Istvan Pallagi、Andras Toro、Odon Farkas

  DOI：10.1021/jo00101a013

  日期：1994.11

  Different products are formed, depending on the para substituent (R) when 2,6-dichlorobenzoquinone N-chloroimine (1b) reacts with the anion of the 4-substituted phenol (2). If the group R can leave as a cation (i.e., R is an electrofugal leaving group) such as H, CH(2)NMe(2), CH2OH, etc., then the reaction yields indophenol (3), the normal Gibbs product. If the group R cannot leave as a cation such as CH3, the final product of the reaction will be type 10, 1,1-disubstituted 2,5-cyclohexadienone. If the group R is OH or NH2, then the reaction gives the corresponding benzoquinone 4 or benzoquinone imine 1 and 2,6-dichlorobenzoquinone imine (1d). In all these cases the reaction proceeds at a 1:1 stoichiometry. If, however, the group R can leave as an anion (i.e., R is nucleofugal leaving group) such as halogen, alkoxy, or OCH(2)Ph, then the reaction proceeds at a 1:2 stoichiometry. In this case the reaction of a second mole of phenolate with type 26 intermediate yields the indophenol product 3 and the oxidized product of the phenol. If the two ortho positions of the phenolate are substituted then the oxidized product of the phenol will be the corresponding benzoquinone. The mechanism of the reaction has been studied by kinetic and nonkinetic (NMR) methods. It has been concluded that the first step of the mechanism is a single electron transfer (SET) from the phenolate to the benzoquinone N-chloroimine 1b which is the rate-determining process in most of the cases. In some of the nucleofugal cases the final oxidation, involving the second mole of phenolate, is the rate-determining step. For the radical reaction three different alternatives are suggested: a combination of radicals in a solvent cage (direct reaction) and two different chain reactions (chain A and chain B). Quantum chemical calculations revealed that the direct reaction and the chain A mechanisms were energetically more favored than chain B. The reaction shows an extremely large para selectivity although the substitution does follow a radical mechanism.