10-methyl-9-(iodomethyl)anthracene | 27998-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-methyl-9-(iodomethyl)anthracene
• 英文别名: 9-iodomethyl-10-methyl-anthracene；9-Jodmethyl-10-methyl-anthracen；9-Methyl-10-jodmethyl-anthracen；9-(Iodomethyl)-10-methylanthracene
• CAS: 27998-91-0
• 化学式: C₁₆H₁₃I
• 分子量: 332.184
• InChiKey: JZVPBFSWJCRTEB-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±24.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  10-methyl-9-(iodomethyl)anthracene 在 乙醚 、 magnesium 、 苯 作用下， 生成 9-甲基-10-[2-(10-甲基蒽-9-基)乙基]蒽
  参考文献：
  名称：

  231.蒽和9-甲基蒽与过氧化二叔丁基衍生的自由基的反应

  摘要：

  DOI：

  10.1039/jr9560001108
• 作为产物：
  描述：

  甲基碘化镁 、 蒽醌 在 乙醚 、 苯 作用下， 生成 10-methyl-9-(iodomethyl)anthracene
  参考文献：
  名称：

  The Synthesis of Some 9,10-Dialkylanthracenes and 4,9-Dialkylbenzthiophanthrenes

  摘要：

  DOI：

  10.1021/ja01224a029

文献信息

• ‘Lepidopterene’ and its dimethylderivative ; Formation of three σ bonds through formal 5πs + 5πs thermal cycloaddition
  作者：G. Felix、R. Lapouyade、A. Castellan、B. Bouas-Laurent、J. Gaultier、C. Hauw

  DOI：10.1016/s0040-4039(00)71879-x

  日期：1975.1

  previous reports, the colourless products obtained in the preparation of 1,2 bis (9′-anthranyl) ethanes are not the photoisomers 4 but new polycyclic compounds of type 3 which we propose to call lepidopterenes, on account of their suggestive shape.

  与以前的报告相反，在制备1,2-二（9'-蒽基）乙烷中获得的无色产物不是光异构体4，而是3型的新多环化合物，鉴于其暗示的形状，我们建议将其称为鳞翅目。
• Carcinogenicity of derivatives of polynuclear compounds
  作者：Richard M. Peck、Tie Keng Tan、Evelyn B. Peck

  DOI：10.1021/jm00234a015

  日期：1976.12
• Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions
  作者：Xian Man Zhang、Frederick G. Bordwell、Joseph E. Bares、Jin Pei Cheng、Brian C. Petrie

  DOI：10.1021/jo00063a025

  日期：1993.5

  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.
• 474. Substituted anthracene derivatives. Part III. Further examples of 1 : 5-anionotropic rearrangements
  作者：G. M. Badger、R. S. Pearce

  DOI：10.1039/jr9500002314

  日期：——
• Ultraviolet Absorption Spectra of 9,10-Dihydroanthracenes
  作者：Donald D. Phillips、James Cason

  DOI：10.1021/ja01131a513

  日期：1952.6