2-(4-iodophenyl)[1,4]benzoquinone | 895728-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-iodophenyl)[1,4]benzoquinone
• 英文别名: 2-(4-iodophenyl)cyclohexa-2,5-diene-1,4-dione；2-4-Iodophenyl)-1,4-benzoquinone
• CAS: 895728-37-7
• 化学式: C₁₂H₇IO₂
• 分子量: 310.091
• InChiKey: GJVKVMMYMKDZMO-UHFFFAOYSA-N

物化性质

• 熔点：
  130-135 °C
• 沸点：
  393.2±41.0 °C(Predicted)
• 密度：
  1.821±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  碘苯 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 2-(4-iodophenyl)[1,4]benzoquinone
  参考文献：
  名称：

  Transition Metal-Free Direct C–H Functionalization of Quinones and Naphthoquinones with Diaryliodonium Salts: Synthesis of Aryl Naphthoquinones as β-Secretase Inhibitors

  摘要：

  A novel ligand-free, transition metal-free direct C-H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.

  DOI：

  10.1021/jo501467v

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。
• Mn-Catalyzed 1,6-conjugate addition/aromatization of <i>para</i>-quinone methides
  作者：Bobin Yang、Wei Yao、Xiao-Feng Xia、Dawei Wang

  DOI：10.1039/c8ob01057a

  日期：——

  A series of ferrocenyl triazole ligands have been synthesized and characterized, which proved to be effective for the Mn-catalyzed 1,6-conjugate addition/aromatization of para-quinone methides.

  一系列二茂铁三唑配体已被合成和表征，证明对锰催化的1,6-共轭加成/芳构化反应具有有效性，该反应针对对醌亚甲基。
• Practical C−H Functionalization of Quinones with Boronic Acids
  作者：Yuta Fujiwara、Victoriano Domingo、Ian B. Seiple、Ryan Gianatassio、Matthew Del Bel、Phil S. Baran

  DOI：10.1021/ja111152z

  日期：2011.3.16

  quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through

  已经开发了多种硼酸对多种醌的直接官能化。这种可扩展的反应在室温下在开放烧瓶中使用廉价试剂很容易进行：在过硫酸盐助氧化剂存在下催化硝酸银（I）。醌的范围很广，各种烷基和芳基硼酸都可以进行有效的交叉偶联。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。该方法已应用于复杂的底物，包括类固醇衍生物和法呢基天然产物。
• Direct C-H Arylation of Quinones with Anilines
  作者：Marc Lamblin、François-Xavier Felpin、Guillaume Naturale、Jean Dessolin

  DOI：10.1055/s-0031-1291163

  日期：2012.7

  We discovered that anilines were suitable for the direct C–H arylation of benzoquinone in the presence of tert-butyl nitrite. This new reaction proceeds through the in situ formation of a diazonium hydroxide species. The coupling can be carried out at room temperature under neutral, additive-free, metal-free, and aqueous conditions, allowing an environmentally friendly procedure.

  我们发现苯胺适用于在亚硝酸叔丁酯存在下苯醌的直接 C-H 芳基化。这种新反应是通过原位形成氢氧化重氮物质来进行的。偶联可在室温、中性、无添加剂、无金属和水性条件下进行，从而实现环保程序。