allyl-trimethyl-[1,4]benzoquinone | 99337-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl-trimethyl-[1,4]benzoquinone
• 英文别名: Allyl-trimethyl-[1,4]benzochinon；2,3,5-Trimethyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione
• CAS: 99337-36-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: KTOXBQAHMNIDCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl-trimethyl-[1,4]benzoquinone 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 6-hydroxy-5,7,8-trimethylchroman
  参考文献：
  名称：

  Al-Khayat, Isam; Dean, Francis M.; France, Steven N., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1301 - 1310

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,5-trimethyl-6-prop-2-en-1-ylphenol 在 盐酸 、 sodium hydroxide 、 steam 、 三氯化铁 作用下， 生成 allyl-trimethyl-[1,4]benzoquinone
  参考文献：
  名称：

  The Chemistry of Vitamin E. XXIII. A New Synthesis of 2,4,6,7-Tetramethyl-5-hydroxycoumaran and of 2-Methyl-5-hydroxycoumaran. Oxidation Products of the Tetramethylcoumaran¹

  摘要：

  DOI：

  10.1021/ja01864a064

文献信息

• Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20060281809A1

  公开（公告）日：2006-12-14

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  披露了治疗或抑制线粒体疾病的方法，如弗里德赖希共济失调（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、卒中（MELAS）或科恩斯-赛尔综合征（KSS），以及在本发明方法中有用的化合物，如α-生育酚醌。还披露了用于治疗其他疾病的方法和化合物。还披露了用于评估受试者代谢状态和治疗效果的能量生物标志物。还披露了调节、正常化或增强能量生物标志物的方法，以及用于这些方法的化合物。
• Tail variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20070072943A1

  公开（公告）日：2007-03-29

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、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）或科恩斯-萨耶综合症（KSS），以及在本发明方法中有用的化合物。本发明还公开了评估受试者代谢状态和治疗效果有用的能量生物标志物。
• REDOX-ACTIVE THERAPEUTICS FOR TREATMENT OF MITOCHONDRIAL DISEASES AND OTHER CONDITIONS AND MODULATION OF ENERGY BIOMARKERS
  申请人：Miller Guy M.

  公开号：US20100222436A1

  公开（公告）日：2010-09-02

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明揭示了治疗或抑制线粒体疾病的方法，如弗里德雷希共济失调症（FRDA）、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）或柯恩斯-萨耶综合症（KSS），以及在所述方法中有用的化合物，如α-生育酚醌。本发明还揭示了用于治疗其他疾病的方法和化合物。还揭示了有用于评估受试者代谢状态和治疗效果的能量生物标志物。本发明还揭示了调节、规范或增强能量生物标志物的方法，以及用于此类方法的化合物。
• Redox-active Therapeutics For Treatment Of Mitochondrial Diseases And Other Conditions And Modulation Of Energy Biomarkers
  申请人：Edison Pharmaceuticals, Inc.

  公开号：EP2471530A1

  公开（公告）日：2012-07-04

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德雷希共济失调（FRDA）、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）或卡恩斯-赛尔综合征（KSS），以及用于本发明方法的化合物，如α-生育酚醌。本发明还公开了用于治疗其他疾病的方法和化合物。本发明还公开了用于评估受试者代谢状态和治疗效果的能量生物标志物。还公开了调节、正常化或增强能量生物标志物的方法，以及用于此类方法的化合物。
• Novel <i>ipso</i>-Substitution of <i>p</i>-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of <i>p</i>-Quinones and Protected <i>p</i>-Dihydroquinones
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Kenji Takahashi、Nobuhisa Fukuda、Yasuyuki Kita

  DOI：10.1021/jo970418o

  日期：1997.8.1

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.