2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone | 67913-13-7

• 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: 2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone
• 英文别名: 2,3-Dimethoxy-5-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione
• CAS: 67913-13-7
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: SEYSVDDVMLFAFR-UHFFFAOYSA-N

物化性质

• 沸点：
  361.4±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone 在 sodium tetrahydroborate 、 乙醇 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 di-tert-butyl 2-allyl-5,6-dimethoxy-3-methyl-1,4-phenylene dicarbonate
  参考文献：
  名称：

  [EN] QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS
  [FR] COMPOSÉS DONNEURS D'OXYDE NITRIQUE À BASE DE QUINONE

  摘要：

  本发明涉及具有喹诚基结构的一氧化氮供体化合物，涉及其制备方法以及它们在治疗病理状况中的应用，其中一氧化氮缺乏在它们的发病机制中起重要作用。

  公开号：

  WO2013060673A1
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 ammonium cerium(IV) nitrate 、 溴 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.33h， 生成 2-allyl-3-methyl-5,6-dimethoxy-1,4-benzoquinone
  参考文献：
  名称：

  烯基氢醌醚与氧化亚铁或硝酸铈铵的氧化脱甲基反应合成泛醌和甲萘醌类似物

  摘要：

  发现在2,4,6-吡啶三甲酸作为催化剂的存在下，用氧化亚铁或硝酸铈铵对甲基化的烯基对苯二酚醚进行脱甲基，得到的泛醌2，甲萘醌2及其类似物的产率为53％至89％。已经报道了合成起始烯基氢醌醚以及2,4,6-吡啶三羧酸及其衍生物的新方法。

  DOI：

  10.1016/0040-4020(80)85034-4

文献信息

• [EN] QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS FOR OPHTHALMIC USE<br/>[FR] COMPOSÉS DONNEURS D'OXYDE NITRIQUE À BASE DE QUINONE POUR UNE UTILISATION OPHTALMIQUE
  申请人：NICOX SA

  公开号：WO2014063923A1

  公开（公告）日：2014-05-01

  The present invention relates to novel nitric oxide donor compounds for the use in the treatment and/or prophylaxis of hypertensive glaucoma, normotensive glaucoma and ocular hypertension.

  本发明涉及用于治疗和/或预防高血压性青光眼、正常眼压青光眼和眼压增高的新型一氧化氮供体化合物。
• Synthesis of Crown Ethers Related to Ubiquinones
  作者：Andreas Merz、Manfred Rauschel

  DOI：10.1055/s-1993-25945

  日期：——

  Crown ethers in which the two methoxy groups of ubiquinone-0 (2,3-dimethoxy-5-methyl-1, 4-benzoquinone) are replaced by oligoethylene glycol bridges have been obtained in five straightforward steps in 35-40% overall yield from 5-methylpyrogallol. A Fremy salt oxidation of a phenolic precursor is used in the final step. The further elaboration of crown ether analogues of ubiquinone-2 was achieved by enol geranylation of cyclopentadiene adducts of the former quinones and subsequent retro-Diels-Alder reaction. The Claisen rearrangement of 2, 2-dimethoxy-5-methylphenyl allyl ethers and related crown ethers affords ortho- and para-allyl-substituted phenols (3: 1) that are oxidized to give bisnorubiquinone derivatives and their ortho- quinone isomers. All new compounds are characterized by high resolution NMR and mass spectrometry.

  用五个简单步骤从5-甲基吡咯卡酚中获得了冠醚，其中 ubiquinone-0（2,3-二甲氧基-5-甲基-1,4-苯醌）的两个甲氧基被寡聚乙二醇桥替代，整体产率为35-40%。在最终步骤中采用了Fremy盐氧化酚前体。通过对前述醌的环戊二烯加成物进行烯醇香豆烯基化以及随后的逆Diels-Alder反应，进一步开发了ubiquinone-2的冠醚类似物。2,2-二甲氧基-5-甲基苯基烯丙醚及相关冠醚的Claisen重排产生了ortho和para-烯丙基取代的酚（比例为3:1），随后被氧化生成bisnorubiquinone衍生物及其ortho-醌异构体。所有新化合物均通过高分辨率NMR和质谱进行表征。
• Quinone based nitric oxide donating compounds
  申请人：NICOX S.A.

  公开号：EP2722326A1

  公开（公告）日：2014-04-23

  The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.

  本发明涉及具有醌基结构的一氧化氮供体化合物、其制备工艺及其在治疗一氧化氮缺乏在发病机制中起重要作用的病理情况中的用途。
• Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
  作者：Damien Y. Duveau、Pablo M. Arce、Robert A. Schoenfeld、Nidhi Raghav、Gino A. Cortopassi、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.06.104

  日期：2010.9

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.
• Perri, Steven T.; Moore, Harold W., Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1897 - 1905
  作者：Perri, Steven T.、Moore, Harold W.

  DOI：——

  日期：——