邻甲酚α-D-葡糖醛酸 | 22904-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 邻甲酚α-D-葡糖醛酸
• 英文名称: 2-methylphenyl radical
• 英文别名: o-tolyl radical；o-methylphenyl；o-tolyl；o-Benzyl-Radikal；o-Tolyl-Radikal；2-Tolylradikal；o-Cresolalpha-D-Glucuronide
• CAS: 22904-44-5
• 化学式: C₇H₇
• 分子量: 91.1326
• InChiKey: VHYAIWZUUQSEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  二邻甲苯基汞 生成 邻甲酚α-D-葡糖醛酸
  参考文献：
  名称：

  Rasuwaew; Ol'dekop, Zhurnal Obshchei Khimii, 1950, vol. 20, p. 181; engl. Ausg. S. 183

  摘要：

  DOI：

文献信息

• Homogeneous gas-phase formation and destruction of anthranil from o-nitrotoluene decomposition
  作者：Y. Z. He、J. P. Cui、W. G. Mallard、W. Tsang

  DOI：10.1021/ja00220a006

  日期：1988.6

  Discussion sur les implications du mecanisme de la reaction etudiee pour les reactions d'initiation dans la decomposition d'explosifs nitroaromatiques

  讨论 sur les 影响 du mecanisme de la reaction etudiee pour les reactor d'initiation dans la分解 d'explosifs nitroaromatiques
• Investigating the Mechanisms of Aromatic Amine-Induced Protein Free Radical Formation by Quantitative Structure−Activity Relationships: Implications for Drug-Induced Agranulocytosis
  作者：Arno G. Siraki、JinJie Jiang、Ronald P. Mason

  DOI：10.1021/tx900432d

  日期：2010.5.17

  Aromatic amine drugs have been associated with agranulocytosis (neutrophil depletion) for which the mechanism is unknown. We have previously shown that the metabolism of two aromatic amine drugs by human myeloperoxidase (MPO) results in phenyl radical metabolite formation and also in protein free radical formation on MPO. Because the concentration of drug required to produce a maximum signal for MPO protein free radical (MPO(center dot)) detection was different for each drug, this prompted us to consider that other aromatic amines may also show varying degrees of ability to induce MPO(center dot) formation. Immunoassay experiments using the immuno-spin-trapping technique were performed, which evaluated the potency of different aromatic amines containing the aniline substructure to generate the MPO(center dot). Each reaction contained equal amounts of H(2)O(2), 5,5-dimethyl-1-pyrroline-N-oxide, MPO, and variable concentrations of aniline derivatives. Several physicochemical parameters for aniline derivatives were used to derive quantitative structure-activity relationship equations, which showed that the Hammett constant (sigma) best correlated with the MPO(center dot) formation for all aniline derivatives. More statistically robust equations were derived if the anilines were separated into mono- and disubstituted groups. However, some aniline derivatives did not induce MPO(center dot) formation. Using electron spin resonance spectroscopy, we evaluated the ability of all aniline derivatives tested to produce phenyl radical metabolites, as previously shown by spin trapping for the aromatic amine drugs. Interestingly, we found that only those aniline derivatives that produced a phenyl radical also formed MPO(center dot). We propose that the phenyl radical is the reactive free radical metabolite responsible for generating the MPO(center dot).
• Intramolecular hydrogen transfer in the <i>o</i>‐tolyl radical studied by time resolved absorption measurements
  作者：Teijiro Ichimura、Yuji Mori、Minoru Sumitani、Keitaro Yoshihara

  DOI：10.1063/1.450448

  日期：1986.2

  The intramolecular hydrogen transfer rate of o-tolyl radicals has been examined by monitoring the absorption time profile of benzyl radicals formed in the picosecond 266 nm laser photolysis of o-chlorotoluene. The rise time of the benzyl radical absorption, 6.5 ns, was attributed mostly to the rearrangement rate of o-tolyl radicals to benzyl radicals.
• Magnetic Field Effects on the Photodissociation Reaction of Triarylphosphine in Nonviscous Homogeneous Solutions
  作者：Yoshio Sakaguchi、Hisaharu Hayashi

  DOI：10.1021/jp030965f

  日期：2004.4.1

  The magnetic field effects (MFEs) on the photodecomposition reactions of triphenylphosphine and its halogen and methyl derivatives are investigated in fluid solutions. The yield of diarylphosphinyl radicals decreased with increasing magnetic field from 0.1 to 5 T but was stationary below 0.1 T and above 5 T. The MFE becomes larger by the substitution of halogen atoms and the 3- or 4-methyl group. In cyclohexane, the yields of the escaped diaryl phosphinyl radicals at 1 T are reduced to 0.69, 0.55, 0.59, and 0.56 of those at 0 T for triphenylphosphine and its tris(4-chloro), tris(3-methyl), and tris(4-methyl) derivatives, respectively. This magnetic field dependence was ascribed to originate from the deactivation process of the excited triplet state, which is a variant of the d-type triplet mechanism originally proposed by Steiner. The interaction between the closely lying npi* and pipi* states makes their solvent dependence complicated.
• Excess Energy and Structural Dependence of the Rate of Energy Redistribution during the Photodissociation of Iodotoluenes
  作者：John E. Freitas、Hyun Jin Hwang、M. A. El-Sayed

  DOI：10.1021/j100064a013

  日期：1994.3

  The ortho (2-), meta (3-), and para (4-) iodotoluenes (C7H7I) are photodissociated at 266 and 304 nm and studied with state-selective one-dimensional photofragment translational spectroscopy. Angular, velocity, and translational energy distributions are obtained for the ground state I(P-2(3/2)) and spin-orbit excited state I*(P-2(1)/2) iodine atoms produced upon photodissociation. As has been observed in iodobenzene, the ground-state I channel observed in each isomer of iodotoluene exhibits both a prompt alkyl iodide-like dissociation channel following a parallel excitation to the alkyl iodide 3Q0(n,sigma*) repulsive state and curve crossing to the 1Q1(n,sigma*) state, and a slower, indirect dissociation channel following a competitive excitation to aromatic charge-transfer (pi,pi*) predissociative excited states at both 266 and 304 nm. The I* channel observed at both 266 and 304 nm for each isomer results from a prompt dissociation resulting from parallel absorption to an alkyl iodide type 3Q0-(n,sigma*) state. The rapid I and I* dissociative channels observed for each isomer are found to exhibit strong dependence on the excess excitation. This is discussed in terms of a strong coupling between the dissociation coordinate and the more dense vibrational states of the toluene ring. Dissociation times and rates of internal energy redistribution (IER) from the slow dissociative channel (beta) are estimated for each isomer. For 2-iodotoluene, the rate of IER for the slow I channel increases from 20 kcal/mol.ps at 304 nm to 30 kcal/mol.ps at 266 nm, while the rates of IER for 3- and 4-iodotoluene (16 kcal/mol-ps and 15 kcal/mol.ps, respectively) remain unchanged as the photon energy is increased. The difference in the observed excess energy dependence of the rates of IER in these isomers is discussed in terms of the complex coupling schemes between the optical doorway states and the n,sigma* repulsive states that produce the iodine atoms, monitored in the experiment.