4-硝基苄基水杨酸酯 | 85303-65-7

• 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: 4-硝基苄基水杨酸酯
• 英文名称: salicylic acid 4-nitrobenzyl ester
• 英文别名: salicylic acid-(4-nitro-benzyl ester)；Salicylsaeure-(4-nitro-benzylester)；(4-Nitro-benzyl)-salicylat；Chembrdg-BB 5235286；(4-nitrophenyl)methyl 2-hydroxybenzoate
• CAS: 85303-65-7
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: SZSSFMAYGDWSBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  水杨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 4-硝基苄基水杨酸酯
  参考文献：
  名称：

  Caged plant hormones

  摘要：

  The syntheses of 2-nitrobenzyl and 1(2-nitrophenyl)ethyl esters of the plant hormones, gibberellin A(4), abscisic acid, jasmonic acid, 1-naphthylacetic acid and salicylic acid are described. These esters are readily photolysed to the corresponding free acids and, thus, are suitable for the photo-release of these hormones after loading into plant cells.

  DOI：

  10.1016/0031-9422(94)00662-d

文献信息

• Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (<i>o</i>-NosylOXY): A Recyclable Coupling Reagent for Racemization-Free Synthesis of Peptide, Amide, Hydroxamate, and Ester
  作者：Dharm Dev、Nani Babu Palakurthy、Kishore Thalluri、Jyoti Chandra、Bhubaneswar Mandal

  DOI：10.1021/jo500292m

  日期：2014.6.20

  byproducts that can be easily recovered and reused for the synthesis of the same reagent, making the method more environmentally friendly and cost-effective. The synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. The synthesis of the difficult sequences, for example, the islet amyloid polypeptide (22–27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH2)

  酰胺和酯官能团的普遍存在使偶联反应极为重要。尽管可获得许多偶联试剂，但是制备常用且有效的试剂的方法繁琐。这些试剂会产生大量化学废物，并且缺乏可回收性。2-氰基-2-（2-硝基苯磺酰氧基亚氨基）乙酸乙酯（o-NosylOXY）是新一代偶联试剂的第一成员，可产生副产物，这些副产物可以轻松回收并再利用以合成同一试剂，从而使该方法更加环保且具有成本效益。描述了使用该试剂合成酰胺，异羟肟酸酯，肽和酯。困难序列的合成，例如，胰岛淀粉样多肽（22–27）片段（具有C末端Gly，H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH 2）和酰基载体蛋白（65-74）片段（H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH），遵循固相肽合成（SPPS）协议和淀粉样蛋白β（39–42）肽（Boc-Val-Val-IIe-Ala-OMe），遵循溶液相策略得到证明。
• Esterification of Salicylic Acid Using Brønsted Acidic Ionic Liquid based on Keggin Heteropoly Acid
  作者：Fatemeh F. Bamoharram、Majid M. Heravi、Javad Ebrahimi、Nilofar Tavakoli-Hoseini

  DOI：10.1080/15533174.2013.768639

  日期：2014.1.2

  For the first time, a new water stable BrOnsted acidic ionic liquid based on Keggin heteroployacid (HPA) was used as environmentally benign catalytic medium in the esterfication of salicylic acid with aliphatic alcohols, CnH2n+1OH (n = 1-5) and benzylic alcohols, RC6H4CH2OH (R = H, NO2, OCH3). This ionic liquid (IL) afforded excellent yield in both thermal conditions and microwave irradiation. Maximum yields were observed under microwave irradiation. Different reaction runs were conducted by varying the reaction parameters such as molar ratio of reactants, weight of the IL, and reaction period in order to optimize the reaction. The IL was easily recovered and reused many times. No significant loss in catalytic activity was observed on recycling.
• Blicke; Smith, Journal of the American Chemical Society, 1929, vol. 51, p. 1949
  作者：Blicke、Smith

  DOI：——

  日期：——
• Lyman; Reid, Journal of the American Chemical Society, 1917, vol. 39, p. 709
  作者：Lyman、Reid

  DOI：——

  日期：——
• Caged plant hormones
  作者：Jane L. Ward、Michael H. Beale

  DOI：10.1016/0031-9422(94)00662-d

  日期：1995.3

  The syntheses of 2-nitrobenzyl and 1(2-nitrophenyl)ethyl esters of the plant hormones, gibberellin A(4), abscisic acid, jasmonic acid, 1-naphthylacetic acid and salicylic acid are described. These esters are readily photolysed to the corresponding free acids and, thus, are suitable for the photo-release of these hormones after loading into plant cells.