benzyl 2-(4-nitrophenyl)acetate | 6035-06-9

• 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: benzyl 2-(4-nitrophenyl)acetate
• 英文别名: Benzyl p-nitrophenylacetate
• CAS: 6035-06-9
• 化学式: C₁₅H₁₃NO₄
• mdl: MFCD20132535
• 分子量: 271.273
• InChiKey: PVOLVGFQIIACPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  benzyl 2-(4-nitrophenyl)acetate 以 正己烷 、 氯仿 为溶剂， 生成 对硝基苯乙酸 、 苯甲醇
  参考文献：
  名称：

  The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance

  摘要：

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.

  DOI：

  10.1021/ja00113a001
• 作为产物：
  描述：

  苯甲醇 、 2-(4-硝基苯基)乙酰氯 在 吡啶 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 benzyl 2-(4-nitrophenyl)acetate
  参考文献：
  名称：

  苄氧基（4-取代苄氧基）卡宾。恶二唑啉的生成和溶液中自由基对的裂解

  摘要：

  2,2-二苄氧基-5,5-二甲基-Δ3-1,3,4-恶二唑啉在苯中在 110°C 下的热解产生二苄氧基卡宾。用叔丁醇捕获卡宾，得到原甲酸二苄基叔丁酯。在没有卡宾捕获剂的情况下，它会分裂为苄氧羰基和苄基自由基，如用 TEMPO 捕获后者所示。在不存在 TEMPO 和叔丁醇的情况下，自由基在与苯乙酸苄酯偶联和脱羧之间分配，随后形成联苄。通过比较两种可能的酯 ArCH2O(CO)CH2Ph 和 PhCH2O(CO)CH2Ar 的产率，确定了类似的卡宾从苄氧基-(p-取代的-苄氧基)卡宾的优选断裂意义。发现对位的吸电子基团有利于裂解为含有该基团的苄基。数据的哈米特图与 σ- 取代基常数 (r = 0.994, ρ(PhH, 110°C) = 0.7) 给出了最佳拟合，表明 ...

  DOI：

  10.1139/v00-078

文献信息

• Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts
  作者：Kazuaki Ishihara、Masaya Nakayama、Suguru Ohara、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(02)00966-3

  日期：2002.10

  either carboxylic acids or alcohols are normally needed. We found that the direct condensation of equimolar amounts of carboxylic acids and alcohols could be achieved using hafnium(IV) or zirconium(IV) salts. These metal salts are highly effective as catalysts for the selective esterification of primary alcohols with carboxylic acids in the presence of secondary alcohols or aromatic alcohols. The present

  为了提高合成中的原子效率并避免产生环境废物，应避免使用化学计量的缩合试剂或过量的底物。在酯化中，通常需要过量的羧酸或醇。我们发现，使用ha（IV）或锆（IV）盐可以实现等摩尔量的羧酸和醇类的直接缩合。这些金属盐在仲醇或芳族醇的存在下作为伯醇与羧酸选择性酯化的催化剂非常有效。本发明的方法可以用于直接聚酯化并且可以适用于大规模操作。
• Enantioselective organocatalytic Michael addition of 2-arylacetates and 2-arylacetonitriles having an electron-withdrawing group to α,β-unsaturated aldehydes
  作者：Seung Woo Seo、Sung-Gon Kim

  DOI：10.1016/j.tetlet.2012.03.102

  日期：2012.6

  The asymmetric organocatalytic Michael addition reaction of 2-arylacetates and 2-arylacetonitriles having an electron-withdrawing group to α,β-unsaturated aldehydes has been established using diphenylprolinol trimethylsilyl (TMS) ether as organocatalyst. The 2-arylacetates and 2-arylacetonitriles having NO2-, CO2Me-, and CN-functional groups on the aromatic ring can be used in this reaction. The desired

  使用二苯基脯氨醇三甲基甲硅烷基（TMS）醚作为有机催化剂，建立了具有吸电子基团的2-芳基乙酸酯和2-芳基乙腈对α，β-不饱和醛的不对称有机催化迈克尔加成反应。在该反应中可以使用在芳环上具有NO 2-，CO 2 Me-和CN-官能团的2-芳基乙酸酯和2-芳基乙腈。获得所需产物，具有良好至优异的产率和高对映选择性（高达97％ee）。
• Process for producing esterificated condensate
  申请人：——

  公开号：US20040015005A1

  公开（公告）日：2004-01-22

  The present invention provides a method for preparing ester or thioester that can conduct catalytic esterification reaction with an equimolar amount of carboxylic acid and alcohol, or catalytic thioesterification reaction with carboxylic acid and an equimolar amount or small amount of thiol, and can be expected as an industrial method that needs an enormous amount of synthesis in the light of green chemistry. By using hafnium chloride (IV), especially tetravalent hafnium compounds represented by hafnium chloride (IV)•(THF) 2 or hafnium (IV)t-butoxide as a (poly) condensation catalyst, direct condensation reaction is conducted from carboxylic acid and an equimolar amount of alcohol or a little smaller amount of thiol, in the nonpolar solvent such as toluene and the like, in a deoxidization atmosphere and under heating reflux, and the reaction synthesizes ester monomer or thioester monomer, polyester or polythioester. When heating reflux is conducted by using a nonpolar solvent, it is preferable to remove azeotropic water from the reaction system.

  本发明提供了一种制备酯或硫酯的方法，该方法可以与等摩尔量的羧酸和醇进行催化酯化反应，或者与羧酸和等摩尔量或少量硫醇进行催化硫酯化反应，可望作为一种需要大量合成的工业方法，符合绿色化学的原则。通过使用四氯化铪（IV），特别是以四氯化铪（IV）•（THF）2或四氯化铪（IV）t-丁氧基表示的四价铪化合物作为（聚）缩聚催化剂，可以从羧酸和等摩尔量的醇或稍微较少量的硫醇，在非极性溶剂如甲苯等中，在脱氧环境和加热回流下进行直接缩聚反应，合成酯单体或硫酯单体，聚酯或聚硫酯。当使用非极性溶剂进行加热回流时，最好从反应系统中去除共沸水。
• Photoinduced Palladium‐Catalyzed Negishi Cross‐Couplings Enabled by the Visible‐Light Absorption of Palladium–Zinc Complexes
  作者：Irini Abdiaj、Lena Huck、José Miguel Mateo、Antonio de la Hoz、M. Victoria Gomez、Angel Díaz‐Ortiz、Jesús Alcázar

  DOI：10.1002/anie.201808654

  日期：2018.10

  A visible‐light‐induced Negishi cross‐coupling is enabled by the activation of a Pd0–Zn complex. With this photocatalytic method, the scope of deactivated aryl halides that can be employed in the Negishi coupling was significantly expanded. NMR experiments conducted in the presence and absence of light confirmed that the formation of the palladium–zinc complex is key for accelerating the oxidative

  通过激活Pd 0 -Zn络合物，可以实现可见光诱导的Negishi交叉耦合。通过这种光催化方法，可用于Negishi偶联的失活芳基卤化物的范围大大扩大。在有光和无光条件下进行的NMR实验证实，钯锌络合物的形成是加速氧化加成步骤的关键。
• CCCCIII.—Experiments on the synthesis of phenolic aporphines. Part II. The protection of hydroxyls by the carbethoxyl group, and the action of benzyl chloride on nitrophenylacetic acids
  作者：John Masson Gulland、Katherine Isobel Ross、Cyril Joseph Virden

  DOI：10.1039/jr9310002881

  日期：——