3,5-dimethyl-2-phenylcyclohexa-2,5-diene-1,4-dione | 1415250-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dimethyl-2-phenylcyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,6-dimethyl-3-phenyl-1,4-benzoquinone；3,5-dimethyl-2-phenyl-1,4-benzoquinone；4,6-dimethyl-[1,1'-biphenyl]-2,5-dione；4,6-Dimethyl-[1,1'-biphenyl]-2,5-dione
• CAS: 1415250-77-9
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: YNXAUKOKTHKROU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3,5-dimethyl-2-phenylcyclohexa-2,5-diene-1,4-dione 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 生成 2,6-Dimethyl-3-phenyl-hydrochinon
  参考文献：
  名称：

  Optimizing the lifetimes of phenoxonium cations derived from vitamin E via structural modifications

  摘要：

  通过系统合成一系列结构类似于维生素E的新酚类化合物，发现了几种在乙腈中经电化学氧化形成抗水解反应的酚氧烯二磁性阳离子的立体位阻化合物。

  DOI：

  10.1039/c5ob01868d
• 作为产物：
  描述：

  2,6-二甲基-2,5-环己二烯-1,4-二酮 、 苯硼酸 在 iron sulfide 、 dipotassium peroxodisulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以75.6%的产率得到3,5-dimethyl-2-phenylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway

  摘要：

  一种新型铁介导的醌和吡啶类似物与芳基硼酸直接C-H芳基化反应已开发出来，使用二氯甲烷和水作为溶剂，在常温下进行。FeS被用作高效的催化剂，详细推测并阐述了反应机理。

  DOI：

  10.1039/c2cc35468c

文献信息

• Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids
  作者：Arghya Deb、Srimanta Manna、Arun Maji、Uttam Dutta、Debabrata Maiti

  DOI：10.1002/ejoc.201300743

  日期：2013.8

  The arylation of C–H bonds to generate heteroaryl–aryl (Het–Ar) and arylated quinone (Quin–Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het–Ar and Quin–Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic

  C-H键的芳基化生成杂芳基-芳基（Het-Ar）和芳基化醌（Quin-Ar）化合物在合成化学中实现可持续目标方面受到了极大的关注。尽管取得了重大进展，广泛的 Het-Ar 和 Quin-Ar 衍生物的芳基化仍然是一项具有挑战性的任务。在本文中，在催化量的廉价 Fe(NO3)3 存在下，使用芳基硼酸将各种杂环芳基化。C-芳基化醌化合物可以通过芳基硼酸与醌或氢醌反应来制备。本方法操作简单，可扩展，不需要杂环或醌的预官能化，并且可以容忍偶联伙伴中的多种官能团。这些品质有望使这种方法对学术和工业用途具有吸引力。
• Generation of Arylated Quinones by Iron-Catalyzed Oxidative Arylation of Phenols: Formal Synthesis of Phellodonin, Sarcodonin ε, Leucomelone and Betulinan A
  作者：Arghya Deb、Soumitra Agasti、Tapish Saboo、Debabrata Maiti

  DOI：10.1002/adsc.201301084

  日期：2014.3.10

  Biologically and pharmaceutically relevant arylated quinones (Quin‐Ar) have been synthesized via direct CH arylation of a variety of phenols using arylboronic acids. An inexpensive, environmentally friendly iron catalyst, ferric sulphate, Fe2(SO4)3, was employed in this operationally simple and efficient method.

  生物学和药物相关芳基化醌（奎恩基-Ar）已经合成经由直接Ç  H的各种使用芳基硼酸的酚芳基化。在这种操作简单而有效的方法中采用了一种廉价，环保的铁催化剂，硫酸铁，Fe 2（SO 4）3。
• The Direct Arylation of Benzoquinones with Arylboronic Acid Promoted by Iron(II) Oxalate
  作者：Yibo Huang、Dan Guan

  DOI：10.3184/174751913x13794472538144

  日期：2013.11

  Arylations of various quinones with several arylboronic acids have been developed. The reactions proceed readily at ambient temperature using iron(II) oxalate as a catalyst and potassium persulfate as a co-oxidant. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone.

  已经开发了多种醌与几种芳基硼酸的芳基化。该反应在环境温度下使用草酸铁 (II) 作为催化剂和过硫酸钾作为助氧化剂很容易进行。推测该机制是通过亲核自由基加成到醌并原位再氧化所得二氢醌来进行的。
• FeSO4-promoted direct arylation of benzoquinones with ArB(OH)2 or ArBF3K
  作者：Kimihiro Komeyama、Tetsuya Kashihara、Ken Takaki

  DOI：10.1016/j.tetlet.2012.12.031

  日期：2013.2

  FeSO4 center dot 7H(2)O was proven to work as effective promoter for the direct arylation of benzoquinones with aryl boronic acids in the presence of K2S2O8. In the arylation, slow addition of iron solution was crucial to efficiently proceed with the reaction. Interestingly, the Fe-mediated arylation could be converted into a catalytic reaction by using hydroquinones, instead of benzoquinones, or addition of ascorbic acid. (C) 2012 Elsevier Ltd. All rights reserved.
• Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway
  作者：Jian Wang、Shan Wang、Gao Wang、Ji Zhang、Xiao-Qi Yu

  DOI：10.1039/c2cc35468c

  日期：——

  A novel iron-mediated direct C–H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.

  一种新型铁介导的醌和吡啶类似物与芳基硼酸直接C-H芳基化反应已开发出来，使用二氯甲烷和水作为溶剂，在常温下进行。FeS被用作高效的催化剂，详细推测并阐述了反应机理。