1,3',4',8,9,10-hexahydro-2',5,6,7',8,8'-hexamethyl-2',8-bis(4,8,12-trimethyltridecyl)-spiro-dipyran>-3(2H),5'-<5H-1>benzopyran-6'(2'H)-one | 91465-78-0

• 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: 1,3',4',8,9,10-hexahydro-2',5,6,7',8,8'-hexamethyl-2',8-bis(4,8,12-trimethyltridecyl)-spiro-dipyran>-3(2H),5'-<5H-1>benzopyran-6'(2'H)-one
• 英文别名: 2',5,6,7',8,8'-Hexamethyl-2',8-bis(4,8,12-trimethyltridecyl)spiro[1,2,9,10-tetrahydropyrano[3,2-f]chromene-3,5'-3,4-dihydrochromene]-6'-one
• CAS: 91465-78-0
• 化学式: C₅₈H₉₆O₄
• 分子量: 857.398
• InChiKey: LBZILIZDKITSKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.4
• 重原子数：
  62
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3',4',8,9,10-hexahydro-2',5,6,7',8,8'-hexamethyl-2',8-bis(4,8,12-trimethyltridecyl)-spiro-dipyran>-3(2H),5'-<5H-1>benzopyran-6'(2'H)-one 、 盐酸 、 乙醇 生成 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3-[2-[6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-5-yl]ethyl]-5,6-dimethylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  ZAXAROVA, E. I.;SHUANNOV, K. A.-V.;ALEKSEEV, S. M.;EVSTIGNEEVA, R. N., KISLORODSODERZHASHCHIE GETEROTSIKLY: BCEC. SOVESHCH.: TEZ. DOKL./KRASNODA+

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-α-生育酚 在 sodium hydroxide 、 sodium azide 、 硫酸 、 溴 、 sodium dodecyl-sulfate 作用下， 以 甲醇 、 phosphate buffer 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 1,3',4',8,9,10-hexahydro-2',5,6,7',8,8'-hexamethyl-2',8-bis(4,8,12-trimethyltridecyl)-spiro-dipyran>-3(2H),5'-<5H-1>benzopyran-6'(2'H)-one
  参考文献：
  名称：

  5a-α-生育酚叠氮化物的合成及其对1-(5a-α-生育酚)-1,2,3-三唑的[2+3]-环加成反应

  摘要：

  具有 1 位取代基的 1,2,3-三唑类化合物源自 α-生育酚（维生素 E），通过 5a-叠氮基-α-生育酚乙酸酯与炔烃的 1,3-偶极环加成反应合成，并经过全面分析表征. 提供了化合物的 NMR 光谱和具有截短的类异戊二烯侧链的衍生物的晶体结构。生育酚部分在碱性介质中很容易裂解，这是在显示 pH 依赖性药物释放的递送系统中使用的先决条件。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500898

文献信息

• Novel tocopherol compounds I. Bromination of α-tocopherol — reaction mechanism and synthetic applications
  作者：T. Rosenau、W.D. Habicher

  DOI：10.1016/0040-4020(95)00421-4

  日期：1995.7

  including the occurrence of an ortho-quinone methide, not as a radical-chain reaction, contrary to earlier reports. The ortho-quinone methide intermediate is also produced by oxidation of a-tocopherol with silver oxide and can be trapped in the presence of electron-rich dienophiles in a hetero-Diels-Alder reaction to form novel dichromanes in high yields.

  与较早的报道相反，α-生育酚的溴化过程显示为两步过程，其中包括邻醌甲基化物的发生，而不是自由基链反应。邻苯二甲酮甲基化物中间体也可通过α-生育酚与氧化银的氧化反应制得，并可在富电子二烯亲和体存在下，通过杂Diels-Alder反应捕获，以高收率形成新型重铬烷。
• 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.