4-[5-Oxo-2-phenyl-oxazol-(4E)-ylidenemethyl]-benzoic acid methyl ester | 329023-63-4

• 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: 4-[5-Oxo-2-phenyl-oxazol-(4E)-ylidenemethyl]-benzoic acid methyl ester
• 英文别名: Methyl 4-[(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]benzoate
• CAS: 329023-63-4
• 化学式: C₁₈H₁₃NO₄
• mdl: MFCD00487506
• 分子量: 307.306
• InChiKey: OWDXJHGXQNRJKT-UHFFFAOYSA-N

物化性质

• 沸点：
  462.3±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[5-Oxo-2-phenyl-oxazol-(4E)-ylidenemethyl]-benzoic acid methyl ester 在 palladium on activated charcoal 盐酸 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 生成 (+/-)-2-氨基-3-(4-羧基苯基)丙酸
  参考文献：
  名称：

  Synthesis of a New Diaminodithiol Bifunctional Chelator for Radiolabeling Biomolecules with Indium(III)

  摘要：

  The synthesis of a new bifunctional ligand 1-(p-carboxybenzyl)-N,N'-bis-[1,1-dimethyl-1-(p-methoxybenzylthio)ethyl]-ethylenediamine-N,N'-diacetic acid, di-t-butyl ester (1, nbi6ss) is described. It consists of a carboxybenzyl group substituted on a carbon atom of the ethylenediamine moiety of a hexadentate ligand, which has been found to have a very high affinity for In(III). The gem-dimethylthiol groups and the carboxylic acid groups of the ligand were protected by groups that can be removed under mild conditions after conjugation to a peptide or protein. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00424-5
• 作为产物：
  描述：

  马尿酸乙酯 、 对甲酰基苯甲酸甲酯 生成 4-[5-Oxo-2-phenyl-oxazol-(4E)-ylidenemethyl]-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of a New Diaminodithiol Bifunctional Chelator for Radiolabeling Biomolecules with Indium(III)

  摘要：

  The synthesis of a new bifunctional ligand 1-(p-carboxybenzyl)-N,N'-bis-[1,1-dimethyl-1-(p-methoxybenzylthio)ethyl]-ethylenediamine-N,N'-diacetic acid, di-t-butyl ester (1, nbi6ss) is described. It consists of a carboxybenzyl group substituted on a carbon atom of the ethylenediamine moiety of a hexadentate ligand, which has been found to have a very high affinity for In(III). The gem-dimethylthiol groups and the carboxylic acid groups of the ligand were protected by groups that can be removed under mild conditions after conjugation to a peptide or protein. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00424-5

文献信息

• Asymmetric Trienamine Catalysis for the Construction of Structurally Rigid Cyclic α,α-Disubstituted Amino Acid Derivatives
  作者：Hao Jiang、Björn Gschwend、Łukasz Albrecht、Signe Grann Hansen、Karl Anker Jørgensen

  DOI：10.1002/chem.201101539

  日期：2011.8.8

  stereoselective Diels–Alder reactions with olefinic azlactones by asymmetric trienamine catalysis. The obtained cycloadducts are easily transformed into the corresponding cyclic α,α‐disubstituted N‐protected amino acid methyl esters under mild reaction conditions. Furthermore, it is demonstrated that in situ ligation of the crude cycloaddition products with amino acid hydrochloride salts leads to the

  通过不对称的三烯胺催化，显示2,4-二烯醛与烯烃氮杂内酯发生高度立体选择性的狄尔斯-阿尔德反应。在温和的反应条件下，将获得的环加合物轻松转化为相应的环状α，α-二取代的N-保护的氨基酸甲基酯。此外，已证明粗制环加成产物与氨基酸盐酸盐的原位连接导致以单罐方式形成非天然二肽基序。
• Khan, Saadia Razi; Ghouri, Nida; Karim, Aneela, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 5, p. 980 - 985
  作者：Khan, Saadia Razi、Ghouri, Nida、Karim, Aneela、Naz, Farzana、Fakhri, Muhammad Imran、Perveen, Shahnaz、Khan, Khalid Mohammed、Taha, Muhammad、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——
• Cross-trienamines in Asymmetric Organocatalysis
  作者：Kim Søholm Halskov、Tore Kiilerich Johansen、Rebecca L. Davis、Marianne Steurer、Frank Jensen、Karl Anker Jørgensen

  DOI：10.1021/ja3068269

  日期：2012.8.8

  Cross-conjugated trienamines are introduced as a new concept in asymmetric organocatalysis. These intermediates are applied in highly enantioselective Diels-Alder and addition reactions, providing functionalized bicyclo[2.2.2]octane compounds and gamma'-addition products, respectively. The nature of the transformations and the intermediates involved are investigated by computational calculations and NMR analysis.
• Synthesis of a New Diaminodithiol Bifunctional Chelator for Radiolabeling Biomolecules with Indium(III)
  作者：Yizhen Sun、Arthur E. Martell、Michael J. Welch

  DOI：10.1016/s0040-4020(00)00424-5

  日期：2000.7

  The synthesis of a new bifunctional ligand 1-(p-carboxybenzyl)-N,N'-bis-[1,1-dimethyl-1-(p-methoxybenzylthio)ethyl]-ethylenediamine-N,N'-diacetic acid, di-t-butyl ester (1, nbi6ss) is described. It consists of a carboxybenzyl group substituted on a carbon atom of the ethylenediamine moiety of a hexadentate ligand, which has been found to have a very high affinity for In(III). The gem-dimethylthiol groups and the carboxylic acid groups of the ligand were protected by groups that can be removed under mild conditions after conjugation to a peptide or protein. (C) 2000 Elsevier Science Ltd. All rights reserved.