β-methoxy-β-(4-methoxyphenyl)ethylalcohol | 102673-48-3

• 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: β-methoxy-β-(4-methoxyphenyl)ethylalcohol
• 英文别名: 2-methoxy-2-(4-methoxyphenyl)ethanol；4,β-dimethoxy-phenethyl alcohol；4,β-Dimethoxy-phenaethylalkohol；2-Methoxy-2-(4-methoxyphenyl)ethanol
• CAS: 102673-48-3
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: DEFGMDWGWVECKE-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：

  β-methoxy-β-(4-methoxyphenyl)ethylalcohol 以 吡啶 为溶剂， 生成 (+/-)-4'-O-methylcherylline
  参考文献：
  名称：

  Studies on tetrahydroisoquinolines. XXV. A synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines; Total synthesis of (.+-.)-cherylline.

  摘要：

  四种 4-苯基-1, 2, 3, 4-四氢异喹啉（8b, c, f, g）是由两种简单的合成物--氧化苯乙烯和苄胺（2b-e）通过 β-羟基苯乙胺（3b-e）以高收率制备的。另一方面，从 4-苄氧基苯乙烯氧化物（11）得到的 β-甲氧基苯乙基甲磺酸盐（16）与苄胺（2a）偶联得到 N-苄基-β-甲氧基苯乙胺（17）。通过对 17.4'-O-Methylcherylline (18) 的酸处理，还通过相同的途径合成了 (±)-cherylline (1)。

  DOI：

  10.1248/cpb.33.3107
• 作为产物：
  描述：

  2-(4-甲氧基苯基)环氧乙烷 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以55%的产率得到β-methoxy-β-(4-methoxyphenyl)ethylalcohol
  参考文献：
  名称：

  4-甲氧基苯乙烯通过电子转移的染料敏化氧化和二聚化

  摘要：

  4-甲氧基苯乙烯 (1) 与染料（如 Acriflavine、罗丹明 6G 和亚甲蓝）在氧气中在甲醇中敏化的光反应得到 4-甲氧基苯甲醛、其二甲基乙缩醛和 2-甲氧基-2-（4-甲氧基苯基）乙醇作为氧化产物连同相应的二聚体，顺式和反式环丁烷，顺式/反式约。5/95。在对染料的荧光和 T-T 吸收的猝灭研究的基础上，提出氧化和二聚化是通过从 1 到激发的单线态染料的电子转移进行的，但不涉及单线态氧的产生。

  DOI：

  10.1246/bcsj.64.2724

文献信息

• 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.
• Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation
  作者：Buddh Singh、Pankaj Gupta、Asha Chaubey、Rajinder Parshad、Shiromani Sharma、Subhash C. Taneja

  DOI：10.1016/j.tetasy.2008.10.023

  日期：2008.11

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.
• 2-(4'-Methoxyphenyl)-2-methoxyethanol¹
  作者：Fawzy G. Baddar

  DOI：10.1021/ja01633a067

  日期：1954.2
• La Manna,A.; Ghislandi,V., Farmaco, Edizione Scientifica, 1962, vol. 17, p. 19 - 23
  作者：La Manna,A.、Ghislandi,V.

  DOI：——

  日期：——
• Dye-Sensitized Oxygenation and Dimerization of 4-Methoxystyrene through Electron Transfer
  作者：Masanobu Kojima、Yasunao Kuriyama、Hirochika Sakuragi、Katsumi Tokumaru

  DOI：10.1246/bcsj.64.2724

  日期：1991.9

  corresponding dimers, cis- and trans-cyclobutanes in a ratio of cis/trans ca. 5/95. On the basis of quenching studies of fluorescence and T–T absorption of the dyes, the oxygenation and dimerization are proposed to proceed through an electron transfer from 1 to excited singlet dyes but not to involve generation of singlet oxygen.

  4-甲氧基苯乙烯 (1) 与染料（如 Acriflavine、罗丹明 6G 和亚甲蓝）在氧气中在甲醇中敏化的光反应得到 4-甲氧基苯甲醛、其二甲基乙缩醛和 2-甲氧基-2-（4-甲氧基苯基）乙醇作为氧化产物连同相应的二聚体，顺式和反式环丁烷，顺式/反式约。5/95。在对染料的荧光和 T-T 吸收的猝灭研究的基础上，提出氧化和二聚化是通过从 1 到激发的单线态染料的电子转移进行的，但不涉及单线态氧的产生。