pentafluorophenyl-furan-2-carboxylate | 188837-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentafluorophenyl-furan-2-carboxylate
• 英文别名: 2,3,4,5,6-pentafluorophenyl furoate；2-furancarboxylic acid pentafluorophenyl ester；2-Furoic acid, pentafluorophenyl ester；(2,3,4,5,6-pentafluorophenyl) furan-2-carboxylate
• CAS: 188837-55-0
• 化学式: C₁₁H₃F₅O₃
• 分子量: 278.135
• InChiKey: UIHCMTCYMQANRT-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±42.0 °C(Predicted)
• 密度：
  1.574±0.06 g/cm3(Predicted)
• 保留指数：
  1385

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  pentafluorophenyl-furan-2-carboxylate 在 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到N,N'-bis-2-furoylhydrazine
  参考文献：
  名称：

  Pentafluorophenyl ester activation for the preparation of N,N′-diaroylhydrazines

  摘要：

  Procedures are reported for the preparation of N,N'-diaroylhydrazines using pentafluorophenyl (Pfp) ester activation of aryl carboxylic acids. Mild conditions which avoid intermediate protection of ring substituents, allows the synthesis of both symmetrical and unsymmetrical diaroylhydrazines in high yields. The recent discovery of potent HIV-1 integrase inhibition by N,N'-bis-salicylhydrazine (1) highlights the potential importance of this class of compounds. The stability of pre-activated Pfp ester intermediates and the facility with which N,N'-diaroylhydrazines can be synthesized using this procedure (stirring at room temperature in DMF) may make the method particularly attractive for synthesis of hydrazide libraries.

  DOI：

  10.1016/s0040-4020(97)00149-x
• 作为产物：
  描述：

  五氟苯酚 在 4-二甲氨基吡啶 、 palladium diacetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.17h， 生成 pentafluorophenyl-furan-2-carboxylate
  参考文献：
  名称：

  使用醛作为酰基供体通过C–H和C–O键活化进行酯基合成的酯交换反应

  摘要：

  已经开发了一种通过CH和C-O键活化在芳基，杂芳基，烷基N-杂芳基-2-羧酸酯和各种醛之间进行新型酯交换的方法，用于合成多种羧酸酯。提出了一种可能的机理，其中包括母体酯中酰基-O键的氧化加成和醛中sp 2 C-H键的自由基裂解。

  DOI：

  10.1021/jo3012573

文献信息

• Aminolysis of Aryl Ester Using Tertiary Amine as Amino Donor via C–O and C–N Bond Activations
  作者：Yong-Sheng Bao、Bao Zhaorigetu、Bao Agula、Menghe Baiyin、Meilin Jia

  DOI：10.1021/jo4023974

  日期：2014.1.17

  aminolysis reaction between various aryl esters and inert tertiary amines by C–O and C–N bond activations has been developed for the selective synthesis of a broad scope of tertiary amides under neutral and mild conditions. The mechanism may undergo the two key steps of oxidative addition of acyl C–O bond in parent ester and C–N bond cleavage of tertiary amine via an iminium-type intermediate.

  已开发出各种芳基酯与惰性叔胺之间通过C-O和C-N键激活进行的氨解反应，可在中性和温和条件下选择性合成各种叔酰胺。该机理可能经历了两个关键步骤：在母体酯中氧化加成酰基C–O键和通过亚胺基型中间体裂解叔胺的C–N键。
• 1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis
  作者：Sara Cesarini、Nicoletta Colombo、Maurizio Pulici、Eduard R. Felder、Wolfgang K.-D. Brill

  DOI：10.1016/j.tet.2006.08.016

  日期：2006.10

  Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.

  使用TFAA作为脱水剂，通过与2-酰基酰肼通过其N原子之一结合到聚合物载体上的脱水环化反应，生成恶二唑。
• Method for cross-linking peptides
  申请人：Madder Annemieke

  公开号：US09290537B2

  公开（公告）日：2016-03-22

  The present invention relates to a method for cross-linking peptides using an activated furan-moiety. In particular, the present invention provides a method for cross-linking peptides comprising the steps of: a) providing a composition comprising furan-peptides, said furan-peptides comprising at least one amino acid comprising a furan-moiety; b) contacting said composition comprising furan-peptides with second peptides, thereby obtaining a mixture comprising furan-peptides and second peptides; c) adding an activation signal to said mixture of step b), thereby activating said furan-peptides to activated furan-peptides, and d) reacting said activated furan-peptides with said second peptides, thereby cross-linking said activated furan-peptides with said second peptides.

  本发明涉及一种使用活化呋喃基团交联肽的方法。具体而言，本发明提供了一种交联肽的方法，包括以下步骤：a)提供包含呋喃肽的组合物，所述呋喃肽包括至少一种含有呋喃基团的氨基酸；b)将包含呋喃肽的组合物与第二肽接触，从而获得包含呋喃肽和第二肽的混合物；c)向步骤b)的混合物中添加激活信号，从而激活呋喃肽为活化呋喃肽；d)将活化呋喃肽与第二肽反应，从而将活化呋喃肽与第二肽交联。
• Heterogeneous recyclable nano-palladium catalyzed amidation of esters using formamides as amine sources
  作者：Yong-Sheng Bao、Lili Wang、Meilin Jia、Aiju Xu、Bao Agula、Menghe Baiyin、Bao Zhaorigetu

  DOI：10.1039/c5gc02985f

  日期：——

  Catalyzed by supported palladium nanoparticles, a decarbonylative amidation reaction between various aryl esters and formamides by C-O bond activation has been developed for the synthesis of amides.

  在负载的钯纳米颗粒的催化下，已经开发了通过CO键活化的各种芳基酯和甲酰胺之间的脱羰基酰胺化反应，用于酰胺的合成。
• METHOD FOR CROSS-LINKING PEPTIDES
  申请人：Madded Annemieke

  公开号：US20130289239A1

  公开（公告）日：2013-10-31

  The present invention relates to a method for cross-linking peptides using an activated furan-moiety. In particular, the present invention provides a method for cross-linking peptides comprising the steps of: a) providing a composition comprising furan-peptides, said furan-peptides comprising at least one amino acid comprising a furan-moiety; b) contacting said composition comprising furan-peptides with second peptides, thereby obtaining a mixture comprising furan-peptides and second peptides; c) adding an activation signal to said mixture of step b), thereby activating said furan-peptides to activated furan-peptides, and d) reacting said activated furan-peptides with said second peptides, thereby cross-linking said activated furan-peptides with said second peptides.

  本发明涉及一种使用活化的呋喃基团交联肽的方法。具体而言，本发明提供了一种交联肽的方法，包括以下步骤：a）提供包含呋喃肽的组合物，所述呋喃肽包括至少一种含有呋喃基团的氨基酸；b）将包含呋喃肽的组合物与第二肽接触，从而获得包含呋喃肽和第二肽的混合物；c）向步骤b）的混合物中添加激活信号，从而将呋喃肽激活为活化呋喃肽；d）将活化呋喃肽与第二肽反应，从而将活化呋喃肽与第二肽交联。