2-甲氧基-5-(3-甲基丁-2-烯基)环己-2,5-二烯-1,4-二酮 | 80464-91-1

• 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
• 中文名称: 2-甲氧基-5-(3-甲基丁-2-烯基)环己-2,5-二烯-1,4-二酮
• 英文名称: 2-methoxy-5-(3'-methyl-2'-butenyl)-1,4-benzoquinone
• 英文别名: 2-methoxy-5-(3-methyl-2-butenyl)benzoquinone；2-Methoxy-5-(3-methylbut-2-enyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 80464-91-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: OFDFNYYEASRABR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基-5-(3-甲基丁-2-烯基)环己-2,5-二烯-1,4-二酮 在 sodium hydride 、 potassium carbonate 作用下， 以 丙酮 、 paraffin 、 苯 为溶剂， 反应 29.0h， 生成 早熟素Ⅱ
  参考文献：
  名称：

  Uchiyama, M.; Overeem, J. C., Recueil des Travaux Chimiques des Pays-Bas, 1981, vol. 100, # 11, p. 408 - 410

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 甲酸 、 jones reagent 作用下， 以 水 、 丙酮 为溶剂， 反应 2.5h， 生成 2-甲氧基-5-(3-甲基丁-2-烯基)环己-2,5-二烯-1,4-二酮
  参考文献：
  名称：

  Uchiyama, M.; Overeem, J. C., Recueil des Travaux Chimiques des Pays-Bas, 1981, vol. 100, # 11, p. 408 - 410

  摘要：

  DOI：

文献信息

• Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones B, D, and E: The Case of Photoenolization at the <i>p</i>-Benzoquinone-CH₂/CH-π System
  作者：Hai-Wei Yan、Ling-Hao Zhao、Xu Zhang、Ya-Nan Yang、Xiang Yuan、Pei-Cheng Zhang

  DOI：10.1021/acs.jnatprod.1c00830

  日期：2021.11.26

  researched in the homologous meroterpenoids by HPLC monitoring and DFT calculations. A “p-benzoquinone-CH2/CH-π” moiety in the structure was the common key feature for the occurrence of this type of photoenolization reaction. The product transformation processes and universality of this photoinduced irreversible proton transfer reaction were analyzed together with the cytotoxic activities of arnebinones B

  已发现Arnebinones B、E 和 D ( 1-3 )对光敏感，在光触发时会产生复杂多样的质子转移产物。1的独特的两步不可逆分子内质子转移产生了五种比例混合物，其中四种具有有趣的双平面手性。通过HPLC监测和DFT计算，首次在同源类二萜中观察和研究了环状双键前所未有的定向差向异构化平衡。A“对苯醌-CH 2结构中的/CH-π”部分是这种光烯醇化反应发生的共同关键特征。分析了这种光诱导的不可逆质子转移反应的产物转化过程和普遍性，并分析了阿尼比酮 B、D 和 E 及其光反应产物的细胞毒活性。
• [EN] METHOD FOR PREPARING QUINONE COMPOUND<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ QUINONE<br/>[ZH] 一种醌类化合物的制备方法
  申请人：UNIV SHANGHAI TECH

  公开号：WO2021238947A1

  公开（公告）日：2021-12-02

  本发明公开了一种醌类化合物的制备方法。本发明提供了一种醌类化合物的制备方法，其包括下述步骤：在碱的存在下，将如式II所示的化合物和如式III所示的化合物进行缩合反应，得到如式I所示的醌类化合物即可；所述的碱的碱性强于苯酚钠。该方法操作简单，适于工业化生产。
• Synthesis of prenylated quinones by the oxidative degradation approach. Birch vs vinylogous Birch hydrogenolysis (BIHY vs VIBIHY) in controlling 2.DELTA. stereochemistry of the prenyl chain
  作者：Pablo Ballester、Magdalena Capo、Xavier Garcias、Jose M. Saa

  DOI：10.1021/jo00054a012

  日期：1993.1

  Two novel approaches toward prenylated quinones are described. The first (route A) involves the following three basic operations: (a) construction of a 4-hydroxybenzylamine carrying a tertiary allyl alcohol (cinnamyl alcohol) side chain of appropriate length (C5, C-10, etc), followed by (b) vinylogous Birch reductive cleavage with concomitant isomerization of the double bond (vinylogous Birch hydrogenolysis, VIBIHY) and (c) Fremy's salt oxidative degradation of the resulting prenylated phenolic benzylamines to the corresponding quinones. The required phenolic cinnamyl alcohols were successfully synthesized by means of two alternative routes, namely: (1) cyclopalladation of phenolic benzylamines followed by ketovinylation and treatment of the resulting beta-aryl substituted alpha,beta unsaturated ketone with methyllithium and (2) reaction of the dilithio derivatives of the appropriate phenolic benzylamine with the desired alpha,beta unsaturated aldehyde, followed by acid rearrangement. The key feature of this approach, namely, the so-called vinylogous Birch hydrogenolysis (VIBIHY) takes place very efficiently on the phenolic tertiary cinnamyl alcohol stage, provided that the reaction (Li/NH3) is carried out on its bissilylated derivative. Unfortunately, its stereochemistry cannot be properly controlled, as it leads to the formation of ca 2.5:1 (E/Z) mixture of (DELTA2) alkenes. The second generation approach (route B), which solves this problem, requires the following: (a) preparation of a 4-hydroxybenzylamine carrying a 3-methyl-2-buten-1-ol (dimethylallyl alcohol) side chain, or higher homologue, followed by (b) Birch hydrogenolysis (BIHY) and step c above. The key Birch hydrogenolysis takes place with almost complete control of the stereochemically labile DELTA2 double bond, thereby making this approach the one of choice for the synthesis of isoprenyl benzoquinones.