2,2,7,8-tetramethyl-2H-chromen-6-ol | 943744-46-5

• 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-tetramethyl-2H-chromen-6-ol
• 英文别名: Plastochromenol；2,2,7,8-tetramethylchromen-6-ol
• CAS: 943744-46-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: SVTSWWXZOBKQTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,7,8-tetramethyl-2H-chromen-6-ol 在 水 、 三氯化铁 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.5h， 以16%的产率得到8a-hydroxy-2,2,7,8-tetramethyl-2H,8aH-chromen-6-one
  参考文献：
  名称：

  Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives

  摘要：

  Four tocopherol model compounds, the chroman-6-ols (1-4) having the typical substitution pattern of alpha-, beta-, gamma-, and delta-tocopherol (vitamin E), were oxidized to the corresponding para-quinones (5-8), and dehydrogenated to the 2H-chromen-6-ols (17-20) involving initial acetyl protection of the phenolic OH and deprotection as the last step. The chromenols were also converted into the para-quinones (21-24), which existed in the bicyclic hemiketal form, in contrast to the chromanol-derived, monocyclic quinones 5-8, the ketalization behavior agreeing well with computations on the DFT level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.114
• 作为产物：
  描述：

  3,4-dihydro-6-acetoxy-2,2,7,8-tetramethyl-1(2H)-benzopyran 在 甲醇 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2,2,7,8-tetramethyl-2H-chromen-6-ol
  参考文献：
  名称：

  Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives

  摘要：

  Four tocopherol model compounds, the chroman-6-ols (1-4) having the typical substitution pattern of alpha-, beta-, gamma-, and delta-tocopherol (vitamin E), were oxidized to the corresponding para-quinones (5-8), and dehydrogenated to the 2H-chromen-6-ols (17-20) involving initial acetyl protection of the phenolic OH and deprotection as the last step. The chromenols were also converted into the para-quinones (21-24), which existed in the bicyclic hemiketal form, in contrast to the chromanol-derived, monocyclic quinones 5-8, the ketalization behavior agreeing well with computations on the DFT level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.114

文献信息

• Treatment of mitochondrial diseases
  申请人：Walkinshaw Gail

  公开号：US20050065099A1

  公开（公告）日：2005-03-24

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

  这项发明涉及治疗或改善线粒体疾病，如阿尔茨海默病、帕金森病、弗里德雷希共济失调症（FRDA）、小脑共济失调、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）、带有红色纤维的肌阵挛性癫痫（MERFF）、肌萎缩侧索硬化症（ALS）、运动神经元疾病、亨廷顿病、黄斑变性和癫痫等疾病的治疗方法，所述方法使用本文描述的Formula I或Formula II的类胡萝卜素衍生物。
• TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Ampere Life Sciences, Inc.

  公开号：US20130267538A1

  公开（公告）日：2013-10-10

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

  本发明涉及使用式I或式II所描述的色酮衍生物的治疗或改善线粒体疾病的方法，例如阿尔茨海默病、帕金森病、弗里德雷希共济失调症（FRDA）、小脑共济失调、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）、带红纤维的肌阵挛性癫痫（MERFF）、肌萎缩侧索硬化症（ALS）、运动神经元疾病、亨廷顿病、黄斑退化和癫痫。
• [EN] TREATMENT OF MITOCHONDRIAL DISEASES<br/>[FR] TRAITEMENT DE MALADIES MITOCHONDRIALES
  申请人：GALILEO PHARMACEUTICALS INC

  公开号：WO2005032544A1

  公开（公告）日：2005-04-14

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.
• Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives
  作者：Anjan Patel、Thomas Netscher、Lars Gille、Kurt Mereiter、Thomas Rosenau

  DOI：10.1016/j.tet.2007.03.114

  日期：2007.6

  Four tocopherol model compounds, the chroman-6-ols (1-4) having the typical substitution pattern of alpha-, beta-, gamma-, and delta-tocopherol (vitamin E), were oxidized to the corresponding para-quinones (5-8), and dehydrogenated to the 2H-chromen-6-ols (17-20) involving initial acetyl protection of the phenolic OH and deprotection as the last step. The chromenols were also converted into the para-quinones (21-24), which existed in the bicyclic hemiketal form, in contrast to the chromanol-derived, monocyclic quinones 5-8, the ketalization behavior agreeing well with computations on the DFT level. (c) 2007 Elsevier Ltd. All rights reserved.