3-氟苯酚阴离子 | 32376-33-3

• 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: 3-氟苯酚阴离子
• 英文名称: 3-fluorophenolate anion
• 英文别名: m-fluorophenolate；3-fluoro-phenol; deprotonated form；3-Fluorophenolate
• CAS: 32376-33-3
• 化学式: C₆H₄FO
• 分子量: 111.096
• InChiKey: SJTBRFHBXDZMPS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氟苯酚阴离子 、 氯乙酸 生成 (3-氟苯氧基)乙酸
  参考文献：
  名称：

  Skeletal rearrangements preceding CO loss from metastable phenoxymethylene ions derived from phenoxyacetic acid and anisole

  摘要：

  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.

  DOI：

  10.1002/oms.1210281031
• 作为产物：
  描述：

  C₇H₇FO₄P^(1-) 在 sodium chloride alkaline phosphatase from Escherichia coli 、 NaMOPS buffer 、 R₁₆₆S variant 、 zinc(II) sulfate 作用下， 生成 3-氟苯酚阴离子
  参考文献：
  名称：

  碱性磷酸酶单酯酶和二酯酶反应：比较过渡态分析

  摘要：

  经常建议酶催化的磷酰基转移反应通过从其溶液对应物改变的过渡态进行。然而，先前对大肠杆菌碱性磷酸酶 (AP) 的研究表明，这种酶通过松散的解离过渡态催化磷酸单酯的水解，类似于溶液中的过渡态。尽管在溶液中磷酸二酯水解具有更紧密、更缔合的过渡态，但 AP 还表现出催化混杂，具有低水平的磷酸二酯酶活性。因为 AP 在进化上针对磷酸单酯水解进行了优化，所以活性位点环境可能会改变二酯水解的过渡状态，使其与传入和传出基团的键合更松散。为了测试这种可能性，我们已经测量了一系列取代的甲基苯基磷酸二酯的非酶促和 AP 催化的反应速率。beta(lg) 的值和其他数据表明 AP 催化的磷酸二酯水解的过渡态与溶液中的过渡态无法区分。AP 通过识别和稳定类似于水溶液中的过渡态来催化磷酰基转移反应，而不是改变过渡态结构。因此，AP 活性位点能够识别不同的过渡状态，这一特性有助于混杂活动的进化优化。beta(lg) 的值和其他数据表明

  DOI：

  10.1021/ja056528r

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。
• The Role of the Leaving Group in the Dissociation of Radical Anions of 9-(Aryloxymethyl)anthracenes
  作者：Norio Kimura

  DOI：10.1021/ja0028929

  日期：2001.4.1