3-nitrophenyl acetate | 1523-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-nitrophenyl acetate
• 英文别名: m-Nitrophenyl acetate；(3-nitrophenyl) acetate
• CAS: 1523-06-4
• 化学式: C₈H₇NO₄
• mdl: MFCD01314157
• 分子量: 181.148
• InChiKey: HRMRLUUZPLAPAS-UHFFFAOYSA-N

物化性质

• 保留指数：
  1348

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitrophenyl acetate 在 modified cyclodextrin 水 作用下， 以 正庚烷 为溶剂， 生成 间硝基苯酚
  参考文献：
  名称：

  Hydrolysis of nitrophenyl esters catalyzed by modified cyclodextrin in water pools in reversed micelles.

  摘要：

  由于环糊精的催化作用和胶束效应，溶解在有机介质（如含水反向胶束）中的双三甲基氨-β-环糊精二碘化物（2）可催化硝基苯酯的水解，并具有显著的速率加速和/或底物选择性。

  DOI：

  10.1248/cpb.32.4682
• 作为产物：
  描述：

  乙酰溴 、 1-硝基-3-苯基甲氧基苯 在 lithium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40%的产率得到3-nitrophenyl acetate
  参考文献：
  名称：

  Counterattack Mode Differential Acetylative Deprotection of Phenylmethyl Ethers: Applications to Solid Phase Organic Reactions

  摘要：

  A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.

  DOI：

  10.1021/jo801659g

文献信息

• Silver Triflate Catalyzed Acetylation of Alcohols, Thiols, Phenols, and Amines
  作者：Debashis Chakraborty、Rima Das

  DOI：10.1055/s-0030-1259999

  日期：2011.5

  variety of alcohols, thiols, phenols, and amines were subjected to acetylation reaction using acetic anhydride in the presence of catalytic quantity of silver triflate. The method described has a wide range of applications, proceeds under mild conditions, does not involve cumbersome workup, and the resulting products are obtained in high yields within a reasonable time. acetylation - silver triflate -

  在催化量的三氟甲磺酸银存在下，使用乙酸酐对各种醇，硫醇，酚和胺进行乙酰化反应。所描述的方法具有广泛的应用，在温和的条件下进行，不涉及繁琐的后处理，并且在合理的时间内以高收率获得了所得产物。 乙酰化-三氟甲磺酸银-醇-苯酚-硫醇-胺
• Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances
  作者：Santosh Kumar Giri、Rajesh Gour、K. P. Ravindranathan Kartha

  DOI：10.1039/c6ra28882k

  日期：——

  protecting groups such as TBDMS/TBDPS/Tr ethers and isopropylidene/benzylidene acetals present on a substrate unaffected. Regioselective hydroxyl protection in partially protected carbohydrate derivatives/polyhydroxylic compounds was possible and was proved to be a convenient time-saving alternative to the conventional synthesis of such compounds. Easy preparation of the catalyst, mild reaction conditions

  高氯二氮杂嗪，一种具有优异稳定性的基本中性的有机盐，已被发现非常适用于游离的以及部分保护的糖，酚，硫酚，硫醇和其他醇以及胺的乙酰化。高氯酸二氮杂pin鎓催化的乙酰化反应温和，无有机和无溶剂，并且不影响底物上存在的对酸敏感的保护基团，例如TBDMS / TBDPS / Tr醚和异亚丙基/亚苄基乙缩醛。在部分受保护的碳水化合物衍生物/多羟基化合物中进行区域选择性羟基保护是可行的，并被证明是常规合成此类化合物的一种省时的简便方法。容易制备催化剂，温和的反应条件和对环境有益的方案是该反应的显着特征。苯酚和苯硫酚的乙酰化反应所获得的结果可以通过DFT计算获得的局部亲核指数来合理化。
• Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
  作者：Abdol Reza Hajipour、Hirbod Karimi、Morteza Karimzadeh

  DOI：10.1007/s00706-014-1222-9

  日期：2014.9

  AbstractAn efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated

  摘要在无溶剂条件下，以磷酸锌锆为催化剂，研究了一种有效的方法，可在无溶剂条件下以乙酸酐良好且优异的产率对多种醇和酚进行乙酰化。用XRD，电感耦合等离子体发射光谱和扫描电子显微镜对催化剂进行了表征。与现有方法相比，产品易于分离，并且操作流程温和绿色。 图形概要
• Metal ion promoted transesterifications of carboxylate esters. A structure/activity study of the efficacy of Zn2+ and La3+ to catalyze the methanolysis of some aryl and aliphatic esters
  作者：Alexei A. Neverov、N. E. Sunderland、R. Stan Brown

  DOI：10.1039/b414763d

  日期：——

  The methanolysis of various aryl and aliphatic carboxylate esters promoted by methoxide, 1,5,9-triazacyclododecane : Zn2+(-OCH3) and La3+(-OCH3), were studied and the derived rate constants (kOCH3, kcat3:Zn(OCH3) and kcatLa(OCH3)) correlated in various ways. The metal ion catalyzed reactions are very much faster than the background reactions in some cases reaching up to 7 x 10(6)-fold acceleration

  研究了甲醇，1,5,9-三氮杂环十二烷：Zn2 +（-OCH3）和La3 +（-OCH3）促进的各种芳基和脂族羧酸酯的甲醇分解，并得出了速率常数（kOCH3，kcat3：Zn（OCH3）和kcatLa（OCH3））以各种方式相关。当存在浓度为5 mmol dm（-3）时，金属离子催化的反应比背景反应快得多，在某些情况下可达到7 x 10（6）倍的加速。两种金属的数据均显示出与离去基团的pKa呈非线性布朗斯台德相关性，并根据随着pKa增加到大于约14.7的值而从金属配位四面体中间体的形成到分解的速率限制步骤的变化进行了分析。 。对数kOCH3反应对vs的曲线图。每个金属离子的log kcat值表示对芳基酯的敏感性较低，而对脂族酯的敏感性较高。提出了观察的机械原理。
• Montmorillonite K-10 and KSF as remarkable acetylation catalysts
  作者：Ai-Xiao Li、Tong-Shuang Li、Tian-Hui Ding

  DOI：10.1039/a703389c

  日期：——

  Montmorillonite K-10 and KSF catalyse the acetylation of alcohols, thiols, phenols and amines with acetic anhydride in excellent yield.

  蒙脱土K-10与KSF催化醇类、硫醇、酚类及胺类与乙酸酐的乙酰化反应，产率极佳。

表征谱图