6-hydroxy-2,7,8-trimethylchroman-2-carboxylic acid

• 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: 6-hydroxy-2,7,8-trimethylchroman-2-carboxylic acid
• 英文别名: 2,7,8-trimethyl-6-hydroxychroman-2-carboxylic acid；γ-trolox；trolox；6-hydroxy-2,7,8-trimethylchroman-carboxylic acid；(+/-)-6-hydroxy-2,7,8-trimethylchroman-2-carboxylic acid；6-Hydroxy-2,7,8-trimethyl-3,4-dihydrochromene-2-carboxylic acid
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: CBWWWQHHIUXXRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,7,8-trimethylchroman-2-carboxylic acid 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以329 g的产率得到2,7,8-trimethyl-6-hydroxychroman-2-methanol
  参考文献：
  名称：

  [EN] SYNTHESIS OF TOCOTRIENOLS FROM O-CRESOL DERIVATIVES
  [FR] SYNTHÈSE DE TOCOTRIÉNOLS À PARTIR DE DÉRIVÉS DE O-CRÉSOL

  摘要：

  本发明提供了一种环境友好、简便的工艺，用于从商业上可获得的邻甲酚衍生物制备生育三烯酚。

  公开号：

  WO2019053605A1
• 作为产物：
  描述：

  二甲酚 在 copper acetylacetonate 、 N-溴代丁二酰亚胺(NBS) 、 N1,N2-bis(4-hydroxy-2,6-dimethylphenyl)oxalamide 、 二正丁胺 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 125.0 ℃ 、1.2 MPa 条件下， 反应 20.0h， 生成 6-hydroxy-2,7,8-trimethylchroman-2-carboxylic acid
  参考文献：
  名称：

  [EN] SYNTHESIS OF TOCOTRIENOLS FROM O-CRESOL DERIVATIVES
  [FR] SYNTHÈSE DE TOCOTRIÉNOLS À PARTIR DE DÉRIVÉS DE O-CRÉSOL

  摘要：

  本发明提供了一种环境友好、简便的工艺，用于从商业上可获得的邻甲酚衍生物制备生育三烯酚。

  公开号：

  WO2019053605A1

文献信息

• Convenient Preparation of 2,7,8‐Trimethyl‐6‐hydroxychroman‐2‐carboxylic Acid (γ‐Trolox)
  作者：John A. Hyatt

  DOI：10.1080/00397910701648728

  日期：2007.12.1

  Abstract The title chroman is useful in synthesis and as a water‐soluble analog of γ‐tocopherol, a member of the vitamin E family. This new synthesis of γ‐trolox proceeds via selective aromatic demethylation of Trolox, the more easily available 2,5,7,8‐tetramethyl homolog compound. This route is shorter than the previous synthesis, avoids the use of cyanide and methoxybutadiene, and requires no chromatography

  摘要 标题色满可用于合成并作为 γ-生育酚（维生素 E 家族的成员）的水溶性类似物。这种 γ-trolox 的新合成是通过 Trolox 的选择性芳族脱甲基化进行的，Trolox 是更容易获得的 2,5,7,8-四甲基同系物。这条路线比之前的合成更短，避免了氰化物和甲氧基丁二烯的使用，并且不需要色谱法。
• Method for producing optically active chroman-carboxylate
  申请人：Kyuuko Youichi

  公开号：US20060141591A1

  公开（公告）日：2006-06-29

  In the method for producing an optically active chromancarboxylate of the present invention, one of the enantiomers of racemic chromancarboxylic acid is esterified in a solvent containing an alcohol in the presence of a biocatalyst. After the esterification, the other enantiomer, i.e., the non-reacted chromancarboxylic acid is separated out of the reaction mixture to obtain the aimed optically active ester. The optically active chromancarboxylate is useful as the material for medicines, agricultural chemicals, etc. The invention provides an efficient production method thereof which is industrially applicable.

  本发明提供了一种制备光学活性的色环羧酸酯的方法，其中在含有醇的溶剂中，在生物催化剂的存在下，对外消旋色环羧酸的对映体之一进行酯化。酯化后，另一对映体即未反应的色环羧酸从反应混合物中分离出来，以获得目标的光学活性酯。光学活性的色环羧酸酯可用作药物、农药等材料。本发明提供了一种高效的工业应用的生产方法。
• Process for producing chroman compound
  申请人：Tanaka Kazuo

  公开号：US20070179304A1

  公开（公告）日：2007-08-02

  The invention provides a process for producing a chroman compound represented by formula (1), characterized in that the process includes allowing a phenol, an unsaturated compound, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc.

  本发明提供了一种生产由式（1）表示的色酮化合物的方法，其特征在于，该方法包括在水的存在下，使酚、不饱和化合物和甲醛在无催化剂存在下反应，其中水的摩尔量为酚的1到10倍。根据本发明，在无催化剂和温和条件下可以生产高纯度的色酮化合物。此外，本发明提供了一种工业生产该化合物的手段，而不使用大量的酸或碱作为反应促进剂或催化剂，否则会引起副反应、设备腐蚀等问题。
• METHOD FOR PRODUCING OPTICALLY ACTIVE CHROMAN-CARBOXYLATE
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1634958A1

  公开（公告）日：2006-03-15

  In the method for producing an optically active chromancarboxylate of the present invention, one of the enantiomers of racemic chromancarboxylic acid is esterified in a solvent containing an alcohol in the presence of a biocatalyst. After the esterification, the other enantiomer, i.e., the non-reacted chromancarboxylic acid is separated out of the reaction mixture to obtain the aimed optically active ester. The optically active chromancarboxylate is useful as the material for medicines, agricultural chemicals, etc. The invention provides an efficient production method thereof which is industrially applicable.

  在本发明生产光学活性铬羧酸酯的方法中，外消旋铬羧酸的一种对映体在含有醇的溶剂中，在生物催化剂的存在下进行酯化反应。酯化后，从反应混合物中分离出另一种对映体，即未反应的铬羧酸，从而得到光学活性酯。具有光学活性的铬羧酸酯可用作药物、农药等的原料。本发明提供了一种适用于工业的高效生产方法。
• PROCESS FOR PRODUCING CHROMAN COMPOUND
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1710239A1

  公开（公告）日：2006-10-11

  The invention provides a process for producing a chroman compound represented by formula (1) (wherein each of substituents R1 to R6 and X represents a hydrogen atom, a halogen atom, a hydroxyl group, a methoxy group, an ethoxy group, a carboxyl group, a C1 to C12 alkyl group which may have a substituent, a C6 to C12 aryl group which may have a substituent, a C7 to C12 aralkyl group which may have a substituent, or an ester residue; R1 to R4 may be linked to one another; and at least one of the substituents X and R6 is an ester residue), characterized in that the process includes allowing a phenol, an olefin, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc. [F1]

  本发明提供了一种生产由式(1)代表的色烷化合物的工艺(其中取代基R1至R6和X各自代表氢原子、卤素原子、羟基、甲氧基、乙氧基、羧基、可能具有取代基的C1至C12烷基、可能具有取代基的C6至C12芳基、可能具有取代基的C7至C12芳烷基或酯残基；R1至R4可彼此相连；取代基X和R6中至少有一个是酯残基），其特征在于，该工艺包括在无催化剂和水存在的情况下，使苯酚、烯烃和甲醛发生反应，反应物的摩尔量为苯酚的1至10倍。 根据本发明，可以在无催化剂和温和的条件下生产出高纯度的铬化合物。此外，本发明还提供了一种生产该化合物的工业方法，无需使用大量作为反应促进剂或催化剂的酸或碱，否则会引起副反应、设备腐蚀等。 [F1]