5-ethyloxymethyl-γ-tocopherol | 19741-08-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-ethyloxymethyl-γ-tocopherol
• 英文别名: 5-ethoxymethyl-7,8-dimethyltocol；5a-ethoxy-α-tocopherol；5-(Ethoxymethyl)-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
• CAS: 19741-08-3
• 化学式: C₃₁H₅₄O₃
• 分子量: 474.768
• InChiKey: YUCJTWCZSMYMDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium ethanolate 、 5a-bromo-α-tocopherol 以 乙醇 、 正己烷 为溶剂， 反应 1.0h， 以100%的产率得到5-ethyloxymethyl-γ-tocopherol
  参考文献：
  名称：

  Novel tocopherol compounds. III. Reaction of 5a-Bromo-?-tocopherol with Nucleophiles

  摘要：

  The synthesis of different classes of 5a-substituted tocopherols is described. These compounds are potent antioxidants and highly interesting as vitamin E carriers. The reaction of the readily available 5a-bromo-alpha-tocopherol with alcohols and phenols is shown to produce 5a-alklxy-alpha-tocopherols (3-5, 8, 9) and 5a-aryloxy-alpha-tocopherols (6, 7), respectively, with high yields. 5a-alpha-Tocopheryl esters (10, 11) are prepared by reaction with metal carboxylates. 5a-Bromo-alpha-tocopherol is used as well to introduce tocopheryl groupsinto tertiary amines by quaternization, that renders these compounds (13, 14) soluble in water and in common organic solvents. 5a-Bromo-alpha-tocopherol also reacts as an alkylating agent with sterically hindered phenols in a Friedel-Crafts reaction. Phenols not highly substituted are exclusively alkylated in the para position at room temperature or below, whereas at higher temperature the para- as well as the ortho-alkylated product is observed.

  DOI：

  10.1002/prac.199633801123

文献信息

• Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates
  作者：Martina Lahmann、Joachim Thiem

  DOI：10.1016/j.tet.2010.12.066

  日期：2011.3

  alpha-Tocopherol and as a model compound pentamethylchromanol could be transferred into simple and more complex 5a-ether derivatives including galactopyranose as well as ascorbic acid conjugates. Following elaboration of a glucopyranoside spacer element this could be used for tethering the vitamin E and the vitamin C components to give novel conjugates for subsequent biostudies concerning their proposed synergism of antioxidant properties in tissues. (C) 2011 Elsevier Ltd. All rights reserved.
• Oxidations of vitamin E (.alpha.-tocopherol) and its model compound. 2,2,5,7,8-Pentamethyl-6-hydroxychroman. A new dimer
  作者：Cacang Suarna、Donald C. Craig、Keith J. Cross、Peter T. Southwell-Keely

  DOI：10.1021/jo00241a029

  日期：1988.3
• Novel tocopherol compounds. III. Reaction of 5a-Bromo-?-tocopherol with Nucleophiles
  作者：T. Rosenau、W. D. Habicher

  DOI：10.1002/prac.199633801123

  日期：——

  The synthesis of different classes of 5a-substituted tocopherols is described. These compounds are potent antioxidants and highly interesting as vitamin E carriers. The reaction of the readily available 5a-bromo-alpha-tocopherol with alcohols and phenols is shown to produce 5a-alklxy-alpha-tocopherols (3-5, 8, 9) and 5a-aryloxy-alpha-tocopherols (6, 7), respectively, with high yields. 5a-alpha-Tocopheryl esters (10, 11) are prepared by reaction with metal carboxylates. 5a-Bromo-alpha-tocopherol is used as well to introduce tocopheryl groupsinto tertiary amines by quaternization, that renders these compounds (13, 14) soluble in water and in common organic solvents. 5a-Bromo-alpha-tocopherol also reacts as an alkylating agent with sterically hindered phenols in a Friedel-Crafts reaction. Phenols not highly substituted are exclusively alkylated in the para position at room temperature or below, whereas at higher temperature the para- as well as the ortho-alkylated product is observed.