9-methyl-10-phenylanthracene | 13425-08-6

• 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-methyl-10-phenylanthracene
• 英文别名: 9-Methyl-10-phenyl-anthracen；10-phenyl-9-methylanthracene
• CAS: 13425-08-6
• 化学式: C₂₁H₁₆
• 分子量: 268.358
• InChiKey: SHHLOTNZRHOQKT-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  420.6±25.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 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：
  0

反应信息

• 作为反应物：
  描述：

  9-methyl-10-phenylanthracene 在 甲醇 作用下， 生成 9-methyl-10-phenyl-9,10-dihydro-9,10-epidioxido-anthracene
  参考文献：
  名称：

  844.一些内消旋取代的蒽光氧化物的热分解

  摘要：

  DOI：

  10.1039/jr9600004340
• 作为产物：
  描述：

  蒽酮 在 溴 、 溶剂黄146 、 苯基锂 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 9-methyl-10-phenylanthracene
  参考文献：
  名称：

  Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions

  摘要：

  Equilibrium acidities (pK(HA)), reduction potentials E(re)(HA), oxidation potentials E(ox)(HA), and oxidation potentials of the conjugate anions E(ox)(A-) have been measured in dimethylsulfoxide(DMSO) solution for 13 alpha-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn). The equilibrium acidities have been shown to be linearly correlated with Hammett sigma- constants. The similar rho- values for the linear correlations of pK(HA) Vs sigma- for 9-GCH2An (rho- = 13.8) and 10-G-9-MeAn (rho- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities. Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDE(HA)) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDE(HA.-)) of the acidic C-H bonds in 9-GCH2An.- and 10-G-9-MeAn.- radical anions, and (c) the radical cation acidities (pK(HA.+)) of the 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations. Introduction of alpha-CN and alpha-NO2 groups had opposite effects on the strengths (BDE(HA)) of the acidic C-H bonds in 9-GCH2An; the alpha-CN group decreased the BDE(HA) value by 2.5 kcal/mol and the alpha-NO2 increased the BDE(HA) value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An.- radical anions (by 10.6 and 12.5 kcal/mol, respectively). The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol. The 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations are strongly acidic with the pK(HA.+) values estimated in the range of -5 to -11 pK(HA.+) units. Seven linear free energy relationships have been observed.

  DOI：

  10.1021/jo00063a025

文献信息

• Application of Non-Steady-State Kinetics to Resolve the Kinetics of Proton-Transfer Reactions between Methylarene Radical Cations and Pyridine Bases
  作者：Vernon D. Parker、Yixing Zhao、Yun Lu、Gang Zheng

  DOI：10.1021/ja982682k

  日期：1998.12.1

  base reactions in dichloromethane (0.2 M tetrabutylammonium hexafluorophosphate) were observed to increase toward a constant value with increasing extent of reaction. The reactions were studied by derivative cyclic voltammetry (DCV), and rate constants were assigned by comparing the experimental with the theoretical DCV data. The kinetic results rule out a simple second-order proton-transfer reaction

  观察到在二氯甲烷（0.2 M 四丁基六氟磷酸铵）中的四种不同甲基芳烃自由基阳离子-吡啶碱反应的表观氘动力学同位素效应（KIEapp）随着反应程度的增加而向恒定值增加。通过导数循环伏安法 (DCV) 研究反应，并通过将实验与理论 DCV 数据进行比较来指定速率常数。动力学结果排除了简单的二级质子转移反应，并暗示了一种机制，其中首先形成复合物，然后进行质子转移，然后分离产物。在达到稳态之前观察到 KIEapp 是反应依赖程度。
• New Hindered Amide Base for Aryne Insertion into Si–P, Si–S, Si–N, and C–C Bonds
  作者：Milad Mesgar、Justin Nguyen-Le、Olafs Daugulis

  DOI：10.1021/jacs.8b07064

  日期：2018.10.24

  general method for a new, hindered lithium diadamantylamide (LDAM) base-promoted insertion of arynes into Si-P, Si-S, Si-N, and C-C bonds is described. Arynes are generated from easily available aryl triflates and halides. Subsequent reaction of the aryne with silylated phosphines, sulfides, or amines affords the insertion products. Furthermore, a one-step synthesis of anthracenes from aryl halides and

  描述了一种新的受阻锂二金刚胺 (LDAM) 碱促进芳炔插入 Si-P、Si-S、Si-N 和 CC 键的一般方法。芳烃是由容易获得的芳基三氟甲磺酸酯和卤化物生成的。芳炔与甲硅烷基化膦、硫化物或胺的后续反应提供插入产物。此外，还证明了从芳基卤化物和芳基酮一步合成蒽。氰基、芳基、烷基、三氟甲基、乙烯基、甲氧基、氯、氟甚至甲酰基部分与反应条件相容。与四甲基哌啶锂 (LiTMP) 促进的反应相比，新的氨基化锂提供了更高的产率。此外，LDAM 碱的庞大性基本上抑制了芳炔与碱的反应，允许使用芳基卤化物和三氟甲磺酸酯作为限制试剂。
• Preparation of benzocyclobutenols by low temperature reaction of ketone enolates with benzynes
  作者：Sasmita Tripathy、Ranga Reddy、Tony Durst

  DOI：10.1139/v03-099

  日期：2003.9.1

  The reaction of benzynes, generated from halobenzenes with lithium tetramethylpipiperide (LTMP) at –40 to –78 °C, with ketone enolates affords benzocyclobutenols in fair to good yields.Key words: benzyne, ketone enolates, anthracenes, benzocyclobutenol, alkoxides.

  通过在-40至-78°C下使用溴苯与四甲基哌啶锂（LTMP）生成的苯亚烯与酮烯醇盐的反应，可以获得较高产率的苯并环丁醇。关键词：苯亚烯，酮烯醇盐，蒽，苯并环丁醇，烷氧基。
• The oxidation of organic compounds by “singlet” oxygen
  作者：E. McKeown、William A. Waters

  DOI：10.1039/j29660001040

  日期：——

  The normal or “triplet” ground state (3Σg–) of molecular oxygen is that of a biradical, ·O–O·, but “singlet” oxygen (1Δg) OO, which is structurally similar to ethylene, is the initial product of heterolytic decompositions of hydrogen peroxide or of per-acids. “Singlet” oxygen reverts to normal “triplet” oxygen by a bimolecular reaction that produces chemiluminescence but is sufficiently long-lived

  正常或“三联体”基态（3 Σ克- ）分子氧的是一个双自由基的，·O-O·，但“单峰”氧（1 Δ克）O O，其在结构上类似于乙烯，是过氧化氢或过酸的杂化分解的初始产物。“单重态”氧通过双分子反应恢复为正常的“三重态”氧，该化学反应产生化学发光，但寿命足够长，可以作为双烯亲体反应。它在其内消旋位置与蒽环碳氢化合物结合，或添加到合适的1,3-二烯中。
• Cycloaddition of arynes with oxazoles1 : A convenient synthesis of variously substituted polycyclic hydrocarbons
  作者：Gaddam Subba Reddy、M.Vivekananda Bhatt

  DOI：10.1016/0040-4039(80)80254-1

  日期：1980.1

  Substituted polycyclic ethers and hydrocarbons are synthesised by the cycloaddition reaction of arynes with oxazoles.

  通过芳烃与恶唑的环加成反应合成取代的多环醚和烃。