sodium 4-cyanophenolate | 3328-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: sodium 4-cyanophenolate
• 英文别名: sodium p-cyanophenoxide；sodium 4-cyanophenoxide；Natrium-4-cyanophenolat；sodium;4-cyanophenolate
• CAS: 3328-57-2
• 化学式: C₇H₄NO*Na
• 分子量: 141.105
• InChiKey: TXKSMBDQKVGNIZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.36
• 重原子数：
  10
• 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：
  46.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  sodium 4-cyanophenolate 在 ((pentafluorosulfanyl)imino)difluorosulfane 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以42.8%的产率得到S,S-Bis(p-cyanophenoxy)-N-pentafluorosulfanylsulfilimine
  参考文献：
  名称：

  Reactions of pentafluorosulfanyliminodihalosulfanes, SF5NSX2, with nucleophiles. Preparation and characterization of pentafluorosulfanylsulfinylamine, SF5NSO.

  摘要：

  DOI：

  10.1016/s0022-1139(00)82671-8
• 作为产物：
  描述：

  (4-氰基苯基)硫酸氢盐 以 various solvent(s) 为溶剂， 生成 sodium 4-cyanophenolate
  参考文献：
  名称：

  Do Electrostatic Interactions with Positively Charged Active Site Groups Tighten the Transition State for Enzymatic Phosphoryl Transfer?

  摘要：

  The effect of electrostatic interactions on the transition-state character for enzymatic phosphoryl transfer has been a subject of much debate. In this work, we investigate the transition state for alkaline phosphatase (AP) using linear free-energy relationships (LIFERs). We determined k(cat)/K-M for a series of aryl sulfate ester monoanions to obtain the Bronsted coefficient, beta(lg)., and compared the value to that obtained previously for a series of aryl phosphorothioate ester dianion substrates. Despite the difference in substrate charge, the observed Bronsted coefficients for AP-catalyzed aryl sulfate and aryl phosphorothioate hydrolysis (-0.76 +/- 0.14 and -0.77 +/- 0.10, respectively) are strikingly similar, with steric effects being responsible for the uncertainties in these values. Aryl sulfates and aryl phosphates react via similar loose transition states in solution. These observations suggest an apparent equivalency of the transition states for phosphorothioate and sulfate hydrolysis reactions at the AP active site and, thus, negligible effects of active site electrostatic interactions on charge distribution in the transition state.

  DOI：

  10.1021/ja0480421

文献信息

• Importance of Open Structure of Nonmetal Based Catalyst in Hydrogen Bond Promoted Methanolysis of Activated Amide: Structure Dynamics between Monomer and Dimer Enabling Recombinant Covalent, Dative, and Hydrogen Bonds
  作者：Shunsuke Oishi、Junichi Yoshimoto、Susumu Saito

  DOI：10.1021/ja9029494

  日期：2009.7.1

  aminoorganoboron (AOB) compounds that involved a recombinant of covalent, dative, and hydrogen bonds. A combination process occurred via reorganizing elements and bonds between the two major structures (open and closed), which were chemically switchable through precise adjustment of either acidic or basic conditions. The structural dynamics favoring an open structure seem to be more important for catalysis, as represented

  我们揭示了隐藏在一系列氨基有机硼 (AOB) 化合物背后的结构动力学，这些化合物涉及共价键、配位键和氢键的重组。通过重组两个主要结构（开放和封闭）之间的元素和键，发生了一个组合过程，这两个主要结构可以通过精确调整酸性或碱性条件进行化学切换。有利于开放结构的结构动力学似乎对催化更为重要，如活化酰胺的甲醇分解。
• New Synthesis of Optically Active<i>O</i>-Aryl<i>O</i>-Ethyl Phenylphosphonothionates
  作者：Hiromichi YOSHIKAWA

  DOI：10.1271/bbb.63.424

  日期：1999.1

  The mixed anhydride method was applied to synthesize O-aryl O-ethyl phenylphosphonothionate. The reaction of O, O-diethyl phosphorochloridate with O-ethyl phenylphosphonothioic acid afforded O, O-diethyl phosphoric O-ethyl phenylphosphonothioic anhydride in a good yield. This anhydride was converted to O-aryl O-ethyl phenylphosphonothionates by reacting with the appropriate sodium phenoxide. This esterification

  采用混合酸酐法合成了O-芳基O-乙基苯基膦酸酯。O，O-二乙基磷酰氯与O-乙基苯基膦酰硫代酸的反应以良好的收率得到了O，O-二乙基磷酸O-乙基苯基膦酰硫代酸酐。通过与适当的苯甲酸钠反应，将该酸酐转化为O-芳基O-乙基苯基膦酸酯。该酯化反应没有外消旋作用，产生了光学纯的O-乙基O-（4-硝基苯基）苯基膦酰硫酸酯（EPN）和O-（4-氰基苯基）O-乙基苯基膦酸酯（氰基磷）。
• Novel Synthesis, Reactivity, and Stereochemistry of Substituted 3-Trifluoromethyl- and 3-Perfluoroalkyl-3-phenoxyprop-2-enal
  作者：Salem El Kharrat、Philippe Laurent、Hubert Blancou

  DOI：10.1021/jo060764i

  日期：2006.9.1

  Substituted 3-phenoxy-3-perfluoroalkylprop-2-enals 3a−s are synthesized in high yields starting from a gem-iodoacetoxy derivative 1 and phenoxides 2. Then efficient syntheses of push−pull derivatives 4, 5, 8a,b, and nonconjugated analogues 6 and 7 illustrate the synthetic potentialities of 3. Stereochemical studies of these perfluoroalkyl-containing trisubstituted olefinic derivatives 3−8b revealed

  取代的3-苯氧基-3-全氟烷基丙-2-烯醛3a - s从宝石-碘乙酰氧基衍生物1和酚盐2开始高收率地合成。然后推挽衍生物的有效合成4，5，图8a，b，和非共轭类似物6和7示出的合成潜力3。这些含全氟烷基三取代的烯烃衍生物的立体化学研究，3 -图8b显示，4 Ĵ CF在13 C NMR光谱中观察到的偶合常数对于确定它们在溶液中的构型和构象至关重要。上推挽的立体化学溶剂极性效应的化合物3 - 5和图8a，b进行了研究。观察到异常的中等极性对亚氨基烯醇醚衍生物4的立体化学的影响。
• 1,2,3,4-Heterohexatrienes as New Tools for Michael-Type Additions Usable for the Synthesis of Phosphorus Dendrimers
  作者：Anne-Marie Caminade、Jean-Pierre Majoral、Valérie Maraval、Régis Laurent、Bruno Donnadieu

  DOI：10.1055/s-2003-37356

  日期：——

  Linear 1,2,3,4-heterohexatrienes of type H2C=CHP(R)2=NP(R′)2=X (X = O, S) are used in Michael-type additions of various primary or secondary amines and hydrazines. The use of functionalized amines allowed the grafting of other functions, such as a double or a triple bond, a sulfide, an imidazole, or a phenol, and various types of NH2 groups. These groups were used in condensation reactions, leading to the grafting of new functions such as phenols. Thus, the P(R)2=NP(R′)2=X group appears as a new electron withdrawing group, very easily tunable by changing the R′ or X substituents.

  线性1,2,3,4-异构六炔烃的类型H2C=CHP(R)2=NP(R′)2=X（X = O, S）在各种初级或次级胺和肼的迈克尔反应中被使用。功能化胺的使用允许其他功能的接枝，如双键或三键、硫化物、咪唑或酚，以及各种类型的NH2基团。这些基团被用于缩合反应，导致新的功能接枝，例如酚。因此，P(R)2=NP(R′)2=X基团作为一种新的电子吸引基团出现，通过改变R′或X取代基非常容易调节。
• Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism beyond the Protein Matrix
  作者：Alexander Hoffmann、Cooper Citek、Stephan Binder、Arne Goos、Michael Rübhausen、Oliver Troeppner、Ivana Ivanović-Burmazović、Erik C. Wasinger、T. Daniel P. Stack、Sonja Herres-Pawlis

  DOI：10.1002/anie.201301249

  日期：2013.5.10

  structure) hydroxylates phenols with O2 via a stable side‐on peroxide complex, which is similar to the active site of tyrosinase in terms of the ligand environment and its spectroscopic properties. The catalytic oxidation of phenols to quinones proceeds at room temperature in the presence of NEt3 and even non‐native substrates can be oxidized catalytically. The reaction mechanism is analogous to that

  一种新的催化剂（见结构）通过稳定的侧向过氧化物络合物将酚与 O 2羟基化，在配体环境及其光谱特性方面类似于酪氨酸酶的活性位点。在室温下，在 NEt 3存在下，苯酚催化氧化为醌，甚至非天然底物也可以催化氧化。反应机理类似于酶催化反应。