3-methoxy-9-phenylphenanthrene | 94879-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methoxy-9-phenylphenanthrene
• CAS: 94879-58-0
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: NBDDMVOOFFEUMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2,2-diphenyl-1-(4-methoxyphenyl)ethylene 在 氧气 作用下， 以 环己烷 为溶剂， 生成 3-methoxy-9-phenylphenanthrene
  参考文献：
  名称：

  Photochemistry of Stilbenes. II. Substituent Effects on the Rates of Phenanthrene Formation

  摘要：

  DOI：

  10.1021/ja00889a049

文献信息

• Sequential Cross‐Coupling/Annulation of <i>ortho</i> ‐Vinyl Bromobenzenes with Aromatic Bromides for the Synthesis of Polycyclic Aromatic Compounds
  作者：Dong Wei、Meng‐Yao Li、Bin‐Bin Zhu、Xiao‐Di Yang、Fang Zhang、Chen‐Guo Feng、Guo‐Qiang Lin

  DOI：10.1002/anie.201910792

  日期：2019.11.11

  A sequential cross-coupling/annulation of ortho-vinyl bromobenzenes with aromatic bromides was realized, providing a direct and modular approach to access polycyclic aromatic compounds. A vinyl-coordinated palladacycle was proposed as the key intermediate for this sequential process. Excellent chemoselectivity and regioselectivity were observed in this transformation. The practicability of this method

  实现了邻乙烯基溴苯与芳族溴的顺序交叉偶联/环化反应，这提供了直接和模块化的方法来获得多环芳族化合物。乙烯基配位的palladacycle被提议为该顺序过程的关键中间体。在该转化中观察到优异的化学选择性和区域选择性。该方法的实用性因其广泛的底物范围，出色的官能团耐受性以及与所得产物相关的丰富转化而突出。
• 一种稠环化合物的制备方法
  申请人：中国科学院上海有机化学研究所

  公开号：CN111995488B

  公开（公告）日：2022-08-09

  本发明公开了一种稠环化合物III的制备方法。本发明的制备方法包括下述步骤：在溶剂中，在醋酸钯、碱和配体的存在下，将化合物I和化合物II进行如下所示的反应，得到化合物III即可。本发明的制备方法对底物的兼容性较好，可以较简单地通过汇聚式合成短时间内获得多种稠环芳烃化合物，尤其是含杂原子类稠环芳烃更是表现出极其优秀的区域选择性。
• The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in methanol. Homolytic cleavage versus electron-transfer pathways
  作者：Dino Mangion、Donald R. Arnold

  DOI：10.1139/cjc-77-10-1655

  日期：——

  The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6 pi-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.
• Van Ginkel, Frits I. M.; Cornelisse, Jan; Lodder, Gerrit, Journal of the American Chemical Society, 1991, vol. 113, # 11, p. 4261 - 4272
  作者：Van Ginkel, Frits I. M.、Cornelisse, Jan、Lodder, Gerrit

  DOI：——

  日期：——
• <b>Photochemistry of Stilbenes. II. Substituent Effects on the Rates of Phenanthrene Formation</b>
  作者：Frank B. Mallory、Janice T. Gordon、Clelia S. Wood

  DOI：10.1021/ja00889a049

  日期：1963.3