2-methoxy-1-(4-methoxyphenyl)ethanol | 147159-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methoxy-1-(4-methoxyphenyl)ethanol
• 英文别名: 2-methoxy-1-(4-methoxyphenyl)ethan-1-ol；1-(4-Methoxyphenyl)-2-methoxyethanol
• CAS: 147159-76-0
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: JMJVVGAOZVWKPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  甲酸 、 2-methoxy-1-(4-methoxyphenyl)ethanol 在 palladium(II) acetylacetonate 、 ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯 、 甲烷磺酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以34%的产率得到4-methoxyphenethyl formate
  参考文献：
  名称：

  乙二醇衍生物的串联酸/钯催化还原还原重排。

  摘要：

  在本文中，我们描述了酸/ Pd串联催化的乙二醇衍生物向末端甲酸酯的转化。机理研究表明，在[1,2] -H迁移和氧基离去基团的裂解下，底物发生重排成醛。离开的基团被捕获为其甲酸酯，醛被还原并随后酯化为甲酸酯。磺酸可催化醛的重排，而还原步骤则需要独特的催化剂体系，该体系包含Pd（II）-或Pd（0）-前体，其负载量低至0.75 mol％和a，a'-bis（二叔丁基膦基）-邻二甲苯作为配体。还原步骤利用甲酸作为易于处理的转移还原剂。

  DOI：

  10.1002/chem.202000251
• 作为产物：
  描述：

  1-Methoxy-4-(2-methoxy-1-nitrooxy-ethyl)-benzene 在 碳酸氢钠 作用下， 以 乙醚 为溶剂， 生成 2-methoxy-1-(4-methoxyphenyl)ethanol
  参考文献：
  名称：

  苄基自由基阳离子中碳-氢、碳-碳和碳-硅键活化的动力学评价

  摘要：

  对一系列 4-甲氧基-α-取代的甲苯自由基阳离子 (1•+) 中 C-C、C-H 和 C-Si 键断裂之间竞争的详细研究，包括产品研究和动力学分析，是呈现。乙腈中的几个自由基阳离子会发生 C-C 键断裂。此类过程的速率常数由激光闪光光解确定，从 2.8 × 104 (1c•+) 到 1.53 × 106 (1f•+) s-1 不等。C-C 键断裂的活化参数的特点是低活化焓约为 30 kJ mol-1，负活化熵在 -34 至 -55 J mol-1 K-1 范围内。自由基阳离子的去质子化始终是由亲核试剂 [硝酸铈 (IV) 硝酸铵 (CAN) 或硝酸根阴离子] 诱导的二级过程，二级速率常数从 7.7 × 107 (1h•+) 到 8。8 × 108 (1i•+) M-1 s-1 在纯乙腈中（CAN 辅助）和从 0.4 × 108 (1j•+) 到 7.1 × 108 (1i•+) M-1 s-1

  DOI：

  10.1021/ja970940s

文献信息

• Alkoxyl Radicals Generated under Photoredox Catalysis: A Strategy for anti‐Markovnikov Alkoxylation Reactions
  作者：Anne‐Laure Barthelemy、Béatrice Tuccio、Emmanuel Magnier、Guillaume Dagousset

  DOI：10.1002/anie.201806522

  日期：2018.10.15

  involves alkoxyl radicals generated from N‐alkoxypyridinium salts. A wide range of alkenes are smoothly difunctionalized in an anti‐Markovnikov fashion, affording various functionalized alkyl alkyl ethers. Notably, this mild process tolerates a number of functional groups and is efficiently carried out under both batch and flow conditions. Importantly, electron paramagnetic resonance (EPR) experiments

  本文报道的是一种新型的光氧化还原催化的醚合成方法，它涉及由N-烷氧基吡啶鎓盐生成的烷氧基自由基。各种各样的烯烃以反马尔可夫尼可夫的方式平稳地进行双官能化，从而提供了各种官能化的烷基烷基醚。值得注意的是，这种温和的方法可以耐受许多官能团，并且可以在间歇和流动条件下有效地进行。重要的是，通过自旋俘获进行了电子顺磁共振（EPR）实验，以表征参与该自由基/阳离子过程的自由基中间体。
• Effects of para-substituents on the mechanisms of solvolysis of styrene oxides
  作者：Jeffrey J. Blumenstein、Victoria C. Ukachukwu、Ram S. Mohan、Dale L. Whalen

  DOI：10.1021/jo00056a027

  日期：1993.2

  Rate and product studies of the hydronium ion-catalyzed, hydroxide ion-catalyzed, and spontaneous reactions of styrene oxide and its p-CH3O-, p-CH3-, p-Cl-, and P-O2N-derivatives in water solutions have been carried out. A Hammett correlation of log k for the acid-catalyzed reactions vs sigma+ gives a slope rho+ of -4.2 and only diol products are formed. An intermediate in the hydronium ion-catalyzed hydrolysis of p-methoxystyrene oxide is trapped, subsequent to its rate-limiting formation, by azide ion. The spontaneous reactions of p-methylstyrene oxide and styrene oxide yield only diol products, and their reactions in 180-water indicate that greater-than-or-equal-to 98 % and ca. 95 %, respectively, of O-18 is incorporated into the benzyl positions. Nucleophilic addition of water to the benzyl carbon of neutral epoxide is proposed as the mechanism of the primary component of the spontaneous reaction for the p-CH3-, p-H- and p-Cl-substrates on the basis of a Hammett rho of -2.0. The spontaneous rate constant for reaction of p-methoxystyrene oxide is much greater than that expected from a Hammett correlation for the p-CH3-, p-H-, and p-Cl-styrene oxides. This increased rate is attributed to the incursion of a reaction that yields mainly (>80%) p-methoxyphenylacetaldehyde. The regiochemistries of addition of hydroxide ion in O-18-water to p-CH3-, p-H-, and p-Cl-substituted styrene oxides and addition of methoxide ion in methanol to p-CH3H, p-H-, p-Cl-, and P-O2N-substituted styrene oxides were also determined and found to vary as functions of the para substituent. Addition of hydroxide and methoxide ions to the a-carbon is favored by electron-donating groups in the phenyl ring, and addition of these nucleophiles to the beta-carbon is favored by electron-withdrawing groups in the phenyl ring.
• Taeger,E. et al., Journal fur praktische Chemie (Leipzig 1954), 1965, vol. 28, p. 13 - 20
  作者：Taeger,E. et al.

  DOI：——

  日期：——
• Tandem Acid/Pd‐Catalyzed Reductive Rearrangement of Glycol Derivatives
  作者：Tanno A. Schmidt、Benjamin Ciszek、Prasad Kathe、Ivana Fleischer

  DOI：10.1002/chem.202000251

  日期：2020.3.18

  investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2]-H-migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. While the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising

  在本文中，我们描述了酸/ Pd串联催化的乙二醇衍生物向末端甲酸酯的转化。机理研究表明，在[1,2] -H迁移和氧基离去基团的裂解下，底物发生重排成醛。离开的基团被捕获为其甲酸酯，醛被还原并随后酯化为甲酸酯。磺酸可催化醛的重排，而还原步骤则需要独特的催化剂体系，该体系包含Pd（II）-或Pd（0）-前体，其负载量低至0.75 mol％和a，a'-bis（二叔丁基膦基）-邻二甲苯作为配体。还原步骤利用甲酸作为易于处理的转移还原剂。
• A Kinetic Evaluation of Carbon−Hydrogen, Carbon−Carbon, and Carbon−Silicon Bond Activation in Benzylic Radical Cations
  作者：Mauro Freccero、Albert Pratt、Angelo Albini、Conor Long

  DOI：10.1021/ja970940s

  日期：1998.1.1

  A detailed study of the competition between C−C, C−H, and C−Si bond fragmentation in a series of 4-methoxy-α-substituted toluene radical cations (1•+), involving both product studies and kinetic analysis, is presented. C−C bond fragmentation occurs with several radical cations in acetonitrile. The rate constants for such processes, determined by laser flash photolysis, varied from 2.8 × 104 (1c•+)

  对一系列 4-甲氧基-α-取代的甲苯自由基阳离子 (1•+) 中 C-C、C-H 和 C-Si 键断裂之间竞争的详细研究，包括产品研究和动力学分析，是呈现。乙腈中的几个自由基阳离子会发生 C-C 键断裂。此类过程的速率常数由激光闪光光解确定，从 2.8 × 104 (1c•+) 到 1.53 × 106 (1f•+) s-1 不等。C-C 键断裂的活化参数的特点是低活化焓约为 30 kJ mol-1，负活化熵在 -34 至 -55 J mol-1 K-1 范围内。自由基阳离子的去质子化始终是由亲核试剂 [硝酸铈 (IV) 硝酸铵 (CAN) 或硝酸根阴离子] 诱导的二级过程，二级速率常数从 7.7 × 107 (1h•+) 到 8。8 × 108 (1i•+) M-1 s-1 在纯乙腈中（CAN 辅助）和从 0.4 × 108 (1j•+) 到 7.1 × 108 (1i•+) M-1 s-1