9-phenyl-9,10-dihydrophenanthrene | 5235-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-phenyl-9,10-dihydrophenanthrene
• 英文别名: 9,10-dihydro-9-phenylphenanthrane；9-Phenyl-9,10-dihydro-phenanthren
• CAS: 5235-80-3
• 化学式: C₂₀H₁₆
• 分子量: 256.347
• InChiKey: ARVMRQWWYLPTNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  9-phenyl-9,10-dihydrophenanthrene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 xylene 为溶剂， 生成 9-苯基菲
  参考文献：
  名称：

  op het Veld,P.H.G.; Laarhoven,W.H., Journal of the Chemical Society. Perkin transactions II, 1978, p. 915 - 922

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基溴化甲基苯 在 正丁基锂 、 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 75.17h， 生成 9-phenyl-9,10-dihydrophenanthrene
  参考文献：
  名称：

  Functionalized (Benzotriazol-1-yl)methanes as 1,1-Dipole Synthon Equivalents in Diverse Annulations to Aromatic and Heteroaromatic Rings

  摘要：

  The title compounds la-e readily undergo deprotonation and subsequent reactions with the appropriate electrophiles to form intermediates of types 4 and 7 which, upon treatment with Lewis acids, cyclize to afford fused aromatics 5 and 8. Tetrahydronaphthalene 11a, 1,2,3,4-tetrahydrochromanes (11b-d, 13), indanes (16, 18), 9,10-dihydrophenanthrenes (21a-c, 25), and tetrahydro[1,2-alpha]indoles (28, 30) with phenyl, substituted phenyl, and thienyl substituents were prepared in this manner.

  DOI：

  10.1021/jo972156w

文献信息

• Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation
  作者：Tom J. A. Corrie、Liam T. Ball、Christopher A. Russell、Guy C. Lloyd-Jones

  DOI：10.1021/jacs.6b10018

  日期：2017.1.11

  The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates

  已经从机理和制备方面研究了分子内金催化芳基三甲基硅烷对芳烃的芳基化。该反应生成 5 至 9 元环，在研究的 44 个实例中，10 个包含杂原子 (N, O)。芳烃与芳基硅烷的束缚不仅提供了一种工具来探测 Ar-Au-Ar 中间体的构象灵活性的影响，通过芳基-芳基键的长度的系统调制，而且还提供了将中性和电子芳基化的能力在分子间过程中根本不发生反应的劣质芳烃底物。使分子内芳基化也导致了现象学上更简单的反应动力学，总体而言，这些特征促进了对线性自由能关系、动力学同位素效应、以及关于芳基电子需求和构象自由度对二芳基金 (III) 物种还原消除速率影响的第一个定量实验数据。形成一系列芴衍生物的周转限制步骤对芳烃的反应性很敏感，并且对于带有强吸电子取代基的芳烃（σ > 0.43）从还原消除变为 π 络合。一个或两个环上的给电子取代基 (ρ = -2.0) 加速了还原消除，单个 σ 值本质上是可加的。两个芳环之间更长和更灵活的系链导致从
• Triflic acid promoted synthesis of polycyclic aromatic compounds
  作者：Ang Li、Daniel J. DeSchepper、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2009.02.042

  日期：2009.4

  The triflic acid (CF3SO3H) promoted cyclizations of 2-styrylbiaryls are found to be useful for the synthesis of polycyclic aromatic compounds, including functionalized derivatives of polycyclic aromatic compounds and heterocyclic systems. The reaction involves cationic cyclization followed by an elimination of benzene from the intermediate product.

  发现三氟甲磺酸（CF 3 SO 3 H）促进的2-苯乙烯基联芳基的环化可用于合成多环芳族化合物，包括多环芳族化合物的官能化衍生物和杂环体系。该反应涉及阳离子环化，然后从中间产物中消除苯。
• The one-electron oxidation of biphenyl-2-ylethylenes. Subsequent chemical reactivity controlled by electron return or proton transfer
  作者：Ren� Lapouyade、Patrice Villeneuve、Aziz Nourmamode、Jean-Pierre Morand

  DOI：10.1039/c39870000776

  日期：——

  Biphenyl-2-ylethylenes react with (4-BrC6H4)3N˙+SbCl6– to give the radical cation of the electrocyclization product which initiates a protic catalysis to the related fluorenes or, in presence of 2,6-di-t-butylpyridine or water, lead stoicheiometrically to phenanthrenes; with photochemical oxidants only phenanthrenes or 9,10-dihydrophenanthrenes are obtained, with an efficiency related to the polarity

  联苯-2- ylethylenes与反应（4- BRC 6 ħ 4）3 Ñ +的SbCl 6 - ，得到发起质子催化现有芴，或在2,6-二存在下electrocyclization产物的自由基阳离子-叔丁基吡啶或水，从化学计量学上导致菲；用光化学氧化剂只能得到菲或9，10-二氢菲，其效率与溶剂的极性以及三重态供体和自由基离子对的相对能量有关。
• Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes
  作者：Sachin Suresh Bhojgude、Anup Bhunia、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/ol4033094

  日期：2014.2.7

  A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced,1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.
• Diene Reactions, Involving Aromatic Nuclei. A Contribution to the Knowledge of the Phenanthrene System
  作者：Ernst Bergmann、Felix Bergmann

  DOI：10.1021/ja01287a011

  日期：1937.8