2-methyl-3-(3-methylbut-2-enyl)-p-benzoquinone

• 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-methyl-3-(3-methylbut-2-enyl)-p-benzoquinone
• 英文别名: prenyl toluquinone；2-Methyl-3-(3-methylbut-2-enyl)-p-benzoquinone；2-methyl-3-(3-methylbut-2-enyl)cyclohexa-2,5-diene-1,4-dione
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XDDCBWXCMDLLSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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

• 作为产物：
  描述：

  1-[1-(3-methylbut-2-enyl)-1,2-propadienyl]cyclopropanol 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铁 、 三乙胺 作用下， 生成 2-methyl-3-(3-methylbut-2-enyl)-p-benzoquinone
  参考文献：
  名称：

  Transformation of 1-(1,2-propadienyl)cyclopropanols into substituted hydroquinones employing octacarbonyldicobalt

  摘要：

  A novel transformation of 1-(1,2-propadieny])cyclopropanols into substituted 1,4-hydroquinones has been developed utilizing the interaction of 1.2-propadienes and octacarbonyldicobalt (Co-2(CO)(8)) This reaction was applied to the synthesis of vitamin E and K analogs. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00367-0

文献信息

• Concise Synthesis of 1,4‐Benzoquinone‐Based Natural Products as Mitochondrial Complex I Substrates and Substrate‐Based Inhibitors
  作者：Zhenyu Han、Heike Angerer、Iris Bischoff、Yihan Qin、Dennis Stegmann、Karina Tuz、Günter Fritz、Oscar Juarez、Robert Fürst、Dana Lashley、Hamid R. Nasiri

  DOI：10.1002/cmdc.202000307

  日期：2020.12.15

  4‐benzoquinone, a natural product from Pyrola media is described. The synthesis is based on a direct late C−H functionalization of the quinone scaffold. The formation of the natural product was confirmed by means of 2D‐NMR spectroscopy. Additional derivatives were synthesized and tested alongside the natural product as potential substrate and substrate‐based inhibitors of mitochondrial complex I (MCI). The

  描述了一种来自Pyrola 培养基的天然产物 2-甲基-5-（3-甲基-2-丁烯基）-1,4-苯醌的短而有效的一步合成。该合成基于醌支架的直接后期 C-H 功能化。天然产物的形成通过 2D NMR 光谱证实。与天然产物一起合成并测试了其他衍生物作为线粒体复合物 I (MCI) 的潜在底物和底物抑制剂。构效关系研究导致发现了 3-methylbuteneoxide-1,4-anthraquinone ( 1i )，一种 IC 为50的抑制剂5 μM 对 MCI。在针对其他醌转化酶（包括琥珀酸脱氢酶和 Na（+）-易位 NADH：醌氧化还原酶）进行测试时，鉴定出的分子对 MCI 显示出高选择性。此外，鉴定出的抑制剂在基于细胞的增殖试验中也有活性。因此，1 i可以被认为是一种新型的 MCI 化学探针。
• ANTICANCER AGENTS AND PROCESS OF MAKING THEREOF
  申请人：Golden Biotechnology Corporation

  公开号：US20160237012A1

  公开（公告）日：2016-08-18

  Provided herein are compositions and processes of making of anticancer compounds useful for cancer treatments. These cyclohexenone compounds show an unexpected result against certain cancer cells compared to their known analogs.

  本文提供了抗癌化合物的组成和制备方法，可用于癌症治疗。这些环己烯酮化合物与其已知的类似物相比，在某些癌细胞中表现出意想不到的效果。
• [EN] ANTICANCER AGENTS AND PROCESS OF MAKING THEREOF<br/>[FR] AGENTS ANTICANCÉREUX ET PROCÉDÉ DE FABRICATION CORRESPONDANT
  申请人：GOLDEN BIOTECHNOLOGY CORP

  公开号：WO2016133940A1

  公开（公告）日：2016-08-25

  Provided herein are compositions and processes of making of anticancer compounds useful for cancer treatments. These cyclohexenone compounds show an unexpected result against certain cancer cells compared to their known analogs.
• Transformation of 1-(1,2-propadienyl)cyclopropanols into substituted hydroquinones employing octacarbonyldicobalt
  作者：Yufu Owada、Takeshi Matsuo、Nobuharu Iwasawa

  DOI：10.1016/s0040-4020(97)00367-0

  日期：1997.8

  A novel transformation of 1-(1,2-propadieny])cyclopropanols into substituted 1,4-hydroquinones has been developed utilizing the interaction of 1.2-propadienes and octacarbonyldicobalt (Co-2(CO)(8)) This reaction was applied to the synthesis of vitamin E and K analogs. (C) 1997 Elsevier Science Ltd.