9-(4-(trifluoromethyl)phenyl)anthracene | 386-23-2

• 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: 9-(4-(trifluoromethyl)phenyl)anthracene
• 英文别名: 9-[4-(trifluoromethyl)phenyl]anthracene
• CAS: 386-23-2
• 化学式: C₂₁H₁₃F₃
• 分子量: 322.329
• InChiKey: LSMKKSHCLCSFQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(4-(trifluoromethyl)phenyl)anthracene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以90 %的产率得到9-bromo-10-(4-trifluoromethylphenyl)anthracene
  参考文献：
  名称：

  通过不对称有机催化形成苯并噻二嗪-1-氧化物动态拆分亚磺酰亚胺

  摘要：

  通过手性磷酸催化的分子内脱水环化，开发了亚砜亚胺的催化动力学拆分。使用该方法对带有邻酰胺苯基部分的多种外消旋亚砜亚胺进行不对称脱水环化，产生回收的亚砜亚胺和苯并噻二嗪-1-氧化物产物，具有良好至高的对映选择性（ s因子高达61）。手性产物多种衍生化为多种含S-立体中心的S,N-杂环，证明了该方法的价值。

  DOI：

  10.1021/acs.orglett.4c00266
• 作为产物：
  描述：

  2-benzyl-4'-trifluoromethyl-benzophenone 在 氢溴酸 、 溶剂黄146 作用下， 生成 9-(4-(trifluoromethyl)phenyl)anthracene
  参考文献：
  名称：

  The Synthesis and Cyclization of Some o-Benzylphenones^1,2

  摘要：

  DOI：

  10.1021/ja01138a026

文献信息

• Invisible Chelating Effect Exhibited between Carbodicarbene and Phosphine through π–π Interaction and Implication in the Cross-Coupling Reaction
  作者：Wei-Chih Shih、Yun-Ting Chiang、Qing Wang、Ming-Chun Wu、Glenn P. A. Yap、Lili Zhao、Tiow-Gan Ong

  DOI：10.1021/acs.organomet.7b00692

  日期：2017.11.13

  Palladium complexes supported with the mixed ligands carbodicarbene (CDC) and different phosphine ligands (PPh3, PTol3, and PCy3) were prepared, and their molecular structures were characterized. Examination of the structures of 2-PPh3 and 2-PTol3 with cis configuration discloses the existence of an unexpected π–π interaction between one phenyl group of the phosphine and the benzimidazole ring of a

  制备了由混合配体碳二碳烯（CDC）和不同的膦配体（PPh 3，PTol 3和PCy 3）负载的钯配合物，并对其分子结构进行了表征。对具有顺式构型的2-PPh 3和2-PTol 3的结构的研究揭示了膦的一个苯基与CDC的苯并咪唑环之间存在意想不到的π-π相互作用。钯配合物2-PPh 3是一种活性的铃木-宫浦催化剂，具有广泛的底物，包含各种官能团和空间要求。与吸电子芳基溴相反，通过在需氧条件下添加催化量的DMSO，可以提高富电子底物的产品收率。溶液NMR和结构分析表明，CDC和膦配体之间的分子内π-π相互作用对反应的活性具有积极影响，这进一步得到了量子化学计算的支持。
• When Anthracene and Quinone Avoid Cycloaddition: Acid-Catalyzed Redox Neutral Functionalization of Anthracene to Aryl Ethers
  作者：Nan Ding、Zhi Li

  DOI：10.1021/acs.orglett.0c01315

  日期：2020.6.5

  under acid catalysis. Instead, 9-anthracenyl aryl ethers are obtained as unexpected products. Mechanistic studies indicate that the reaction likely undergoes an ionic mechanism between protonated anthracene species and nucleophilic oxygen of 1,4-benzoquinone or 1,4-hydroquinone. A variety of 9-anthracenyl aryl ethers are constructed with this method. Produced anthracenyl aryl ethers are potential scaffolds

  在酸催化下，苯醌和9-苯基蒽几乎没有发生预期的环加成反应。取而代之的是，获得了9-蒽基芳基醚，这是出乎意料的产物。机理研究表明，该反应可能在质子化的蒽类物质与1,4-苯醌或1,4-氢醌的亲核氧之间发生离子机理。用这种方法可以构建多种9-蒽基芳基醚。产生的蒽基芳基醚是新型荧光分子的潜在支架。
• Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study
  作者：Bo Han、Pengchen Ma、Xuefeng Cong、Hui Chen、Xiaoming Zeng

  DOI：10.1021/jacs.9b03328

  日期：2019.6.5

  Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium

  由于芳香性引起的热力学稳定性，多环芳烃是难以加氢的底物。我们在这里报告了在环境温度下多环芳烃的第一个铬和钴催化的区域控制加氢。这些反应由低成本的铬或钴盐与二亚氨基/卡宾配体和甲基溴化镁结合促进，具有高区域选择性和扩大的底物范围，包括并四苯、四苯、并五苯和苝，它们很少被还原。该方法提供了一种具有成本效益的氢化催化方案，具有可扩展性，可用于通过氢化产物的功能化合成四溴和羧基取代的基序。
• Suzuki–Miyaura cross-coupling of bulky anthracenyl carboxylates by using pincer nickel N-heterocyclic carbene complexes: an efficient protocol to access fluorescent anthracene derivatives
  作者：Mizhi Xu、Xingbao Li、Zheming Sun、Tao Tu

  DOI：10.1039/c3cc46663a

  日期：——

  A series of fluorescent (hetero)-aryl substituted anthracene derivatives were readily accessible from the corresponding bulky anthracen-9-yl carboxylates via Suzuki–Miyaura cross-coupling reactions by using pincer nickel N-heterocyclic carbene complex 1 even at the catalyst loading as low as 0.1 mol% in the presence of catalytic amounts of PCy3.

  即使催化剂负载量为在催化量的 PCy3 存在下，含量低至 0.1 mol%。
• METHOD FOR SYNTHESIZING ANTHRACENE DERIVATIVE AND ANTHRACENE DERIVATIVE, LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, ELECTRONIC DEVICE
  申请人：EGAWA Masakazu

  公开号：US20080107918A1

  公开（公告）日：2008-05-08

  It is an object to provide a novel method for synthesizing an anthracene derivative with the small number of steps. It is another object to provide a novel anthracene derivative. It is further another object to provide a light-emitting element, a light-emitting device, and an electronic device, each using the anthracene derivative. A method for synthesizing an anthracene derivative represented by a general formula (1) is provided by coupling a 9-arylanthracene derivative having an active site at a 10-position with a 9-arylcarbazole derivative having an active site in an aryl group using metal, a metal compound, or a metal catalyst.

  本发明的目的是提供一种新颖的合成蒽衍生物的方法，步骤少。另一个目的是提供一种新颖的蒽衍生物。进一步的目的是提供一种使用该蒽衍生物的发光元件、发光装置和电子设备。通过使用金属、金属化合物或金属催化剂将具有10位活性位点的9-芳基蒽衍生物与具有芳基中有活性位点的9-芳基咔唑衍生物偶联，从而提供了一种合成由通式（1）表示的蒽衍生物的方法。