2-甲基苯酚阴离子 | 20217-30-5

• 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: 2-甲基苯酚阴离子
• 英文名称: 2-methylphenolate anion
• 英文别名: o-methylphenol anion；2-methylphenolate；anion of o-cresol；o-methylphenoxide
• CAS: 20217-30-5
• 化学式: C₇H₇O
• 分子量: 107.132
• InChiKey: QWVGKYWNOKOFNN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  8
• 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：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基苯酚阴离子 在 三氟化硼 作用下， 以 various solvent(s) 为溶剂， 生成 C₇H₇BF₃O^(1-)
  参考文献：
  名称：

  Gas-Phase Reactions of Catecholate and Related Anions with BF3 and SiF4

  摘要：

  The gas-phase reactions of the anions of catechol, 4-methylcatechol, resorcinol, and o-cresol with BS and SiF4 have been examined using the flowing afterglow technique. These systems initially form an addition product in a three-body step, and this addition product subsequently participates in fluoride transfer with a second molecule of the reactant neutral. The reactions involving the anions of catechol and 3-methylcatechol exhibit a second primary product channel which is independent of the concentration of the third-body. Results suggest that this bimolecular product is a cyclic species formed in a step involving the ring-closure step and loss of HF. Relative amounts of the two primary products are sensitive to pressure as well as to the identity of the Lewis acid. We explain this behavior in terms of a multiple-well potential energy surface which contains a barrier in the bimolecular product channel.

  DOI：

  10.1021/ja00129a012
• 作为试剂：
  描述：

  在 2-甲基苯酚阴离子 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 1,8-bis(dimethylamino)-2,7-dimethoxynaphthalene 、 邻甲酚
  参考文献：
  名称：

  对于质子化胺缓慢的质子转移，初级动力学同位素效应可忽略不计

  摘要：

  从质子化的1,8-双（二​​甲基氨基）-2,7-二甲氧基萘到碱的质子转移的主要动力学同位素效应（k H / k D）即使对于质子供体和受体具有相似反应的反应也具有单位值p K值，这是预期会导致最大同位素效应的条件。

  DOI：

  10.1039/c39800000141

文献信息

• Nucleophilicity of phenolates in the reaction with p-nitrophenyl acetate in ethanol
  作者：Giuseppe Guanti、Giorgio Cevasco、Sergio Thea、Carlo Dell'Erba、Giovanni Petrillo

  DOI：10.1039/p29810000327

  日期：——

  of p-nitrophenol in the reaction of nine substituted phenolates with p-nitrophenyl acetate has been determined by spectrophotometric measurements in absolute ethanol at 22°. The phenolate anion is the reactive species and competes with ethoxide anion, arising from solvolysis of the phenolate, for nucleophilic attack on the ester carbonyl carbon atoms. From the observed reaction rates the solvolysis constants

  在22°C的无水乙醇中通过分光光度法测定了九种取代酚盐与对硝基苯乙酸酯反应中对硝基苯酚的释放速率。酚盐阴离子是反应性物质，并且与酚盐的溶剂分解产生的乙氧化物阴离子竞争，对酯羰基碳原子进行亲核攻击。从观察到的反应速率获得酚的溶剂分解常数和p K a值。酚盐阴离子的二阶速率常数与p K a相关相应的苯酚的Bronstedβ值为0.57。进行了与芳基硫醚对乙醇中相同底物的亲核反应性的比较。决定速率的步骤可能是芳基硫醚化物反应中离去基团的排出，而苯酚盐反应中亲核试剂的进攻。
• Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate esters
  作者：Dimitrios Stefanidis、Sayeon Cho、Sirano Dhe-Paganon、William P. Jencks

  DOI：10.1021/ja00058a006

  日期：1993.3

  substituted phenolate anions with m-nitrophenyl, p-nitrophenyl, and 3,4-dinitrophenyl formates follow nonlinear BrOnsted-type correlations that might be taken as evidence for a change in the rate-limiting step of a reaction that proceeds through a tetrahedral addition intermediate. However, the correlation actually represents two different BrOnsted lines that are defined by meta- and para-substituted phenolate

  取代苯酚阴离子与间硝基苯基、对硝基苯基和 3,4-二硝基苯基甲酸酯的反应遵循非线性 BrOnsted 型相关性，可以作为反应的限速步骤发生变化的证据。四面体加成中间体。然而，相关性实际上代表了两个不同的布朗斯特线，它们由间位和对位取代的苯酚阴离子以及间位和对位取代的邻氯苯酚阴离子定义。在 ΔpK=0 时，在每一类 BrOnsted 相关性中攻击和离开酚酸阴离子的 BrOnsted 斜率没有可检测的变化，这支持了乙酰基和甲酰基转移反应的协调机制
• Ram, B.; Roy, J.; Sarkar, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 665
  作者：Ram, B.、Roy, J.、Sarkar, A.

  DOI：——

  日期：——
• Skeletal rearrangements preceding CO loss from metastable phenoxymethylene ions derived from phenoxyacetic acid and anisole
  作者：Tineke A. Molenaar-Langeveld、Steen Ingemann、Nico M. M. Nibeering

  DOI：10.1002/oms.1210281031

  日期：1993.10

  AbstractThe loss of CH2˙ from the molecular ion of phenoxyacetic acid and the expulsion of an H˙ atom from ionized anisole lead to phenoxymethylen ions, which fragment predominantly by CO loss on the microsecond time‐scale. Carbon‐13 labelling reveals that ∼90% of the CO molecules expelled from the metastable ions derived from phenoxyacetic acid incorporate the carbon atom from the 1‐position of the phenyl group of the parent compound, whereas the residual CO molecules contain one of the other carbon atoms of the aromatic ring. The 2‐fluoro‐ and 2‐methylphenoxymethylene ions derived from the appropriate aryloxyacetic acids behave similarly, i.e. the carbon atom of the methylene group of the parent compound is not incorporated in the expelled CO molecules. In contrast, ∼45% of the CO molecules eliminated from the metastable phenoxymethylene ions formed from ionized anisole contain the carbon atom of the methyl group, while the remaining part contains the carbon atom from the 1‐position of the phenyl ring of the parent compound. This result is taken as evidence for the occurrence of a skeletal rearrangement of the anisole molecular ion leading to an interchange between the carbon atom of the methyl group and the carbon atom at the 1‐position of the ring. The elimination of CO from the metastable ions generated from either phenoxyacetic acid or anisole gives rise to a composite metastable peak. Conclusive evidence as to the formation of [C7H7O]+ isomers other than the phenoxymethylene ion is not obtained, indicating that the composite metastable peak is a result of two competing reactions both leading to CO loss. Possible mechanisms of these reactions are discussed together with the mechanism of the skeletal rearrangement of the molecular ion of anisole prior to H˙ loss.
• (Alkoxycarbonyl)- and (aryloxycarbonyl)cobalt carbonyls
  作者：Miklos. Tasi、Gyula. Palyi

  DOI：10.1021/om00128a006

  日期：1985.9.1