2,2,7,8-tetramethylchroman-5,6-dione | 14053-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2,7,8-tetramethylchroman-5,6-dione
• 英文别名: 2,2,7,8-tetramethyl-3,4-dihydro-2H-chromene-5,6-dione；2,2,7,8-tetramethyl-chroman-5,6-quinone；2,2,7,8-Tetramethyl-chroman-5,6-chinon；2,2,7,8-Tetramethyl-5,6-ortho-quinonechroman；2,2,7,8-tetramethyl-3,4-dihydrochromene-5,6-dione
• CAS: 14053-19-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: DNGQPGPTMOFPFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,7,8-tetramethylchroman-5,6-dione 在 甲醇 、 硝酸 作用下， 生成 6-hydroxy-2,2,7-trimethyl-3,4-dihydro-2H-chromene-5,8-dione
  参考文献：
  名称：

  John; Emte, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1941, vol. 268, p. 85,99

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2,2,5,7,8-五甲基-2H-1-苯并吡喃-6-酚 在 乙醇 、 硝酸 作用下， 生成 2,2,7,8-tetramethylchroman-5,6-dione
  参考文献：
  名称：

  The Chemistry of Vitamin E. XVII. The Oxidation Products of α-Tocopherol and of Related 6-Hydroxychromans

  摘要：

  DOI：

  10.1021/ja01878a047

文献信息

• [EN] NOVEL METHOD FOR PREPARATION OF ATOVAQUONE<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION D'ATOVAQUONE
  申请人：LUPIN LTD

  公开号：WO2012153162A1

  公开（公告）日：2012-11-15

  Provided is a process of preparation of 2-[trans,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy- 1,4-naphthoquinone, i.e. Atovaquone [I] which is cost effective, green, and eco-friendly process, without separation of any diastereomers or geometric isomers of intermediates obtained during the reactions. Also provided is separation of 'cis' and 'trans ' isomer of intermediates VI, VII and VIII through selective crystallization in an appropriate solvent. A method for converting 2-[cis,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone to 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone in presence of Lewis/ Bronsted acid is also provided. A process for preparation of compound 2-(4-(4- chlorophenyl)- 1 -hydroxy cyclohexyl)-3,4-dihydronaphthalen- 1 (2H)-one [IV] comprising condensation of (1,2-dihydronaphthalen-4-yloxy)trimethylsilane [II] with 4-(4- chlorophenyl)cyclohexanone [III] in presence of Lewis acid in organic solvent. The invention also encompasses a highly efficient and atomeconomic process for synthesis of compound [III] i.e. 4-(4-chlorophenyl)cyclohexanone as well as a process for synthesis of 2-[cis-4-(4'- chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone. Further provided is a process for isomerization of cis- Atovaquone i.e. 2-[cis-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4- naphthoquinone to tnms-Atovaquone i.e. 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3- hydroxy- 1,4-naphthoquinone in presence of Lewis acid.

  提供了一种制备2-[反式,-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌，即阿托喹酮[I]的过程，这是一种具有成本效益、绿色、环保的过程，无需分离在反应过程中获得的中间体的对映异构体或几何异构体。还提供了通过在适当溶剂中选择性结晶来分离中间体VI、VII和VIII的'顺式'和'反式'异构体的方法。还提供了一种在路易斯/布朗斯特酸的存在的条件下将2-[顺式,-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌转化为2-[反式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的方法。还提供了一种制备化合物2-(4-(4-氯苯基)-1-羟基环己基)-3,4-二氢萘-1(2H)-酮[IV]的过程，包括(1,2-二氢萘-4-氧基)三甲基硅烷[II]与4-(4-氯苯基)环己酮[III]在有机溶剂中在路易斯酸的存在的条件下进行缩合。本发明还涵盖了高效且原子经济的合成化合物[III]即4-(4-氯苯基)环己酮的过程以及合成2-[顺式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的过程。还提供了一种在路易斯酸的存在的条件下将顺式-阿托喹酮即2-[顺式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌异构化为反式-阿托喹酮即2-[反式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的过程。
• Reaction of 2,2,5,7,8-pentamethyl-6-chromanol, an α-tocopherol analogue, with NO in the presence of oxygen
  作者：Yoshiko Nagata、Tamamo Nishio、Shigenobu Matsumoto、Hideko Kanazawa、Masataka Mochizuki、Yoshikazu Matsushima

  DOI：10.1016/s0960-894x(00)00563-1

  日期：2000.12

  An alpha -tocopherol model compound, 2,2,5,7,8-pentamethyl-6-chromanol, reacted with nitric oxide (NO) in the presence of various amounts of oxygen to afford four major products. Distribution of the products was varied depending on the ratio of NO and O-2, and the preincubation time of NO and O-2. (C) 2000 Elsevier Science Ltd. All rights reserved.
• John et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1939, vol. 257, p. 173,175
  作者：John et al.

  DOI：——

  日期：——
• John; Emte, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1939, vol. 261, p. 24,28
  作者：John、Emte

  DOI：——

  日期：——
• α-Tocopurple, an Oxidation Product of α-Tocopherol¹
  作者：Vernon L. Frampton、W. A. Skinner、Paris Cambour、Philip S. Bailey

  DOI：10.1021/ja01502a046

  日期：1960.9

  alpha-Tocopurple, an oxidation product of a-tocopherol (vitamin E), has been isolated and its structure proved to be 2,7-dimethyl-6-hydroxy-2-(4,8,12-trimethyltridecyl)-5,8-chromanquinone (111). The three isomeric tetramethyl-beta hydroxychromans (VII, IX, X) have been synthesized and obtained as analytically pure solids. Oxidation of 2,2,7,8-tetramethyl-6-hydroxychroman (VI I) and of 2,2,5,7-tetramethyl-6-hydroxychroman (IX) with ferric chloride in methanol yielded the same hydroxyquinone (XII), thereby proving its structure.