2-methoxy-9,10-diphenylphenanthrene

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 2-methoxy-9,10-diphenylphenanthrene
• 化学式: C₂₇H₂₀O
• 分子量: 360.455
• InChiKey: PACMYGGRKWIRKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 1-碘-2-(4-甲氧基苯基)苯 在 palladium diacetate 、 四丁基氯化铵 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到2-methoxy-9,10-diphenylphenanthrene
  参考文献：
  名称：

  Synthesis of Polycyclic Aromatic Hydrocarbons by the Pd-Catalyzed Annulation of Alkynes

  摘要：

  DOI：

  10.1021/jo9712557

文献信息

• A palladium-catalyzed multi-component annulation approach towards the synthesis of phenanthrenes
  作者：Juan Song、Songjiang Wang、Haisen Sun、Yuxuan Fan、Kang Xiao、Yan Qian

  DOI：10.1039/c9ob00228f

  日期：——

  palladium-catalyzed three-component cascade reaction has been developed for the facile construction of phenanthrene frameworks. The transformation is driven by a controlled reaction sequence of Suzuki–Miyaura coupling followed by the insertion of alkynes, and finally, annulation to yield phenanthrene derivatives via C–H activation. This methodology is able to accommodate a variety of substrates and affords

  已经开发出一种有效的钯催化的三组分级联反应，以方便地构建菲骨架。转化是由可控的Suzuki-Miyaura偶联反应顺序驱动的，然后插入炔烃，最后通过C-H活化进行环化生成菲衍生物。这种方法学能够容纳各种基材，并以良好或优异的产量提供预期的产品。
• Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C−H and C−C Bond Activation
  作者：Congyang Wang、Souvik Rakshit、Frank Glorius

  DOI：10.1021/ja106130r

  日期：2010.10.13

  A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.

  描述了钯催化的 2-苯基苯甲酸与炔烃的分子间形式 [4 + 2] 环化的新方案。吖啶被证明对于高反应效率是必不可少的。菲衍生物以中等至良好的产率形成，无需偶联（伪）卤化物或有机金属物质。
• Phenanthrene Synthesis via Chromium-Catalyzed Annulation of 2-Biaryl Grignard Reagents and Alkynes
  作者：Jianming Yan、Naohiko Yoshikai

  DOI：10.1021/acs.orglett.7b03342

  日期：2017.12.15

  A chromium/2,2′-bipyridine-catalyzed annulation reaction of 2-biarylmagnesium reagents with alkynes is reported. The reaction is applicable to a variety of aryl- and/or alkyl-substituted internal alkynes as well as 2-biaryl and related Grignard reagents, thus affording phenanthrene derivatives in moderate to good yields. The reaction proceeds at the expense of excess alkyne as a hydrogen acceptor and

  据报道，铬/ 2,2'-联吡啶催化2-联芳基镁试剂与炔烃的环化反应。该反应适用于各种芳基和/或烷基取代的内部炔烃以及2-联芳基和相关的格氏试剂，因此以中等至良好的产率提供了菲衍生物。该反应以过量的炔作为氢受体为代价进行，因此不需要外部氧化剂。氘标记实验阐明了反应机理，该机理可能涉及铬上多个分子内C–H活化过程。
• One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/ <i>o</i> ‐chloranil Catalysis
  作者：Kyohei Ozaki、Keiichiro Murai、Wataru Matsuoka、Katsuaki Kawasumi、Hideto Ito、Kenichiro Itami

  DOI：10.1002/anie.201610374

  日期：2017.1.24

  report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group

  在材料科学中，可靠而短的合成多环芳烃和纳米石墨烯的合成路线很重要。在本文中，我们报告了炔烃的高效一步式环扩反应，可接触二芳基菲和相关的纳米石墨烯前体。在阳离子钯/ o存在下氯苯胺催化剂体系和二苯甲酚或二苯并germoles作为π扩展剂，各种二芳基乙炔可在一个步骤中成功转化为具有良好官能团耐受性的9,10-二芳基菲。此外，还证明了1,4-双（苯基乙炔基）苯与二苯基-1,3-丁二炔的π延伸反应，提供了低聚亚芳基产物，这些产物在合成较大的多环芳烃和纳米石墨烯方面具有潜力。
• Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of <i>o</i>-Iodobiphenyls or (<i>Z</i>)-β-Halostyrenes with <i>o</i>-Bromobenzyl Alcohols through Two Sequential C–C Bond Formations Catalyzed by a Palladium Complex
  作者：Masayuki Iwasaki、Yasuhiro Araki、Shohei Iino、Yasushi Nishihara

  DOI：10.1021/acs.joc.5b01693

  日期：2015.9.18

  bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular

  邻溴苄醇已被开发为一种新型的带有亲核和亲电取代基的环化试剂，可轻松合成多环芳烃。钯/电子不足的膦催化剂有效地将邻碘联苯或（Z）-β-卤代苯乙烯与邻溴苄醇偶联，分别制得三亚苯基和菲。目前的级联反应是通过去乙酰化交叉偶联和顺序分子内环化进行的。大量实验数据表明，反应机理涉及1,4-钯迁移的平衡。