salicylic acid pentafluorophenyl ester | 187806-42-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: salicylic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 2-hydroxybenzoate
• CAS: 187806-42-4
• 化学式: C₁₃H₅F₅O₃
• 分子量: 304.173
• InChiKey: NRGOQNHEFSENRY-UHFFFAOYSA-N

物化性质

• 沸点：
  381.9±42.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  salicylic acid pentafluorophenyl ester 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1.2.3.4-Tetrahydro-3.9-dioxo-xanthen
  参考文献：
  名称：

  一种通过一锅克莱森缩合/环化反应合成 1,2-二氢氧杂蒽酮的有效方法

  摘要：

  1,2-二氢氧杂蒽酮 (DHX) 是天然产物的核心结构，也是有机合成中有用的组成部分。到目前为止，它们的研究较少。在本报告中，通过克莱森缩合和O-环化，在废物诱导的中继催化下，在最少有机溶剂的情况下，开发了一种温和、高效、绿色的 1,2-二羟基蒽酮合成方法。副产品（HMDS 或 NH 3 ·H 2第一步的 O) 被证明是第二步的促进剂，它可以在水性介质中有效地进行，而无需添加其他催化剂。使用水杨酸三氟乙酯的反应可以在温和的条件下进行，以确保以高产率生成易受攻击的 DHX。无论取代基类型及其在结构上的位置如何，底物范围都非常广泛。具体来说，DHX 的多功能性通过它们转化为氧杂蒽酮和其他复杂结构来证明。

  DOI：

  10.1039/d1ob00470k
• 作为产物：
  描述：

  五氟苯酚 、 水杨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 以50%的产率得到salicylic acid pentafluorophenyl ester
  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

文献信息

• Hydrazide-Containing Inhibitors of HIV-1 Integrase
  作者：He Zhao、Nouri Neamati、Sanjay Sunder、Huixiao Hong、Shaomeng Wang、George W. A. Milne、Yves Pommier、Terrence R. Burke

  DOI：10.1021/jm960755+

  日期：1997.3.1

  Inhibitors of HIV integrase are currently being sought as potential new therapeutics for the treatment of AIDS. A large number of inhibitors discovered to date contain the o-bis-hydroxy catechol structure. In an effort to discover structural leads for the development of new HIV integrase inhibitors which do not rely on this potentially cytotoxic catechol substructure, NSC 310217 was identified using

  目前正在寻找HIV整合酶抑制剂作为治疗艾滋病的潜在新疗法。迄今为止发现的大量抑制剂含有邻-双-羟基邻苯二酚结构。为了找到开发不依赖于这种潜在的细胞毒性儿茶酚亚结构的新型HIV整合酶抑制剂的结构性线索，基于其指定的结构N-（2-羟基苯甲酰基）-使用三点药效团搜索方法鉴定了NSC 310217 N-（2-羟基-3-苯氧基丙基）肼（1）。从NCI资料库中获得NSC 310217的样品时，它显示出对HIV-1整合酶的有效抑制作用（3'处理IC50 = 0.6微克/ mL）。在本文报道的工作中，我们证明了NSC 310217而不是包含1，它对HIV-1整合酶没有抑制作用，大约由N-（2-羟基苯甲酰基）-N'-（2-羟基-3-苯氧基丙基）肼（6）和N，N'-双水杨基肼7的1：1混合物组成，所有抑制能力都存在化合物7（链转移的IC50 = 0.7 microM）。在随后的关于7的结构活性研究中，研究表明
• Tetra‐Substituted <i>p‐Tert</i> ‐Butylcalix[4]Arene with Phosphoryl and Salicylamide Functional Groups: Synthesis, Complexation and Selective Extraction of f‐Element Cations
  作者：Florian Glasneck、Quirina I. Roode‐Gutzmer、Thorsten Stumpf、Berthold Kersting

  DOI：10.1002/chem.202104301

  日期：2022.2.21

  The tetra-substituted bifunctional calixarene ligand H2L is an effective extraction agent for selective removal of uranyl salts from aqueous rare-earth containing solutions. As the separation factor ßU/Ln is ∼100 in a weakly acidic pH range, a complete separation of uranyl from aqueous trivalent lanthanide solutions is expected to be achieved with few separation steps. The separation factors at pH 6

  四取代双官能杯芳烃配体H 2 L是一种有效的萃取剂，用于从含稀土的水溶液中选择性去除铀酰盐。由于在弱酸性 pH 范围内分离因子ß U/Ln约为 100，因此预计只需很少的分离步骤即可实现铀酰与三价镧系元素水溶液的完全分离。 pH 6.0 时的分离因子为 121 (UO 2 2+ /La 3+ ) 和 70 (UO 2 2+ /Yb 3+ )！
• 2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors
  作者：Xue Zhi Zhao、Elena A. Semenova、B. Christie Vu、Kasthuraiah Maddali、Christophe Marchand、Stephen H. Hughes、Yves Pommier、Terrence R. Burke

  DOI：10.1021/jm070715d

  日期：2008.1.1

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.
• Pentafluorophenyl ester activation for the preparation of N,N′-diaroylhydrazines
  作者：He Zhao、Terrence R. Burke

  DOI：10.1016/s0040-4020(97)00149-x

  日期：1997.3

  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.
• An efficient approach for the synthesis of 1,2-dihydroxanthones enabled by one-pot Claisen condensation/cyclization reactions
  作者：Huaimo Wu、Song Liu、Youyi Wang、Man Yuan、Hong Zhang、Hua Zhou、Lianbo Xiao、Changwu Zheng、Hongxi Xu

  DOI：10.1039/d1ob00470k

  日期：——

  of natural products and useful building blocks in organic synthesis. So far, they have been less studied. In this report, a mild, efficient and green method for the synthesis of 1,2-dihydroxanthones has been developed in one pot through Claisen condensation and O-cyclization under waste-induced relay catalysis with minimum organic solvents. The by-product (HMDS or NH3·H2O) of the first step turned

  1,2-二氢氧杂蒽酮 (DHX) 是天然产物的核心结构，也是有机合成中有用的组成部分。到目前为止，它们的研究较少。在本报告中，通过克莱森缩合和O-环化，在废物诱导的中继催化下，在最少有机溶剂的情况下，开发了一种温和、高效、绿色的 1,2-二羟基蒽酮合成方法。副产品（HMDS 或 NH 3 ·H 2第一步的 O) 被证明是第二步的促进剂，它可以在水性介质中有效地进行，而无需添加其他催化剂。使用水杨酸三氟乙酯的反应可以在温和的条件下进行，以确保以高产率生成易受攻击的 DHX。无论取代基类型及其在结构上的位置如何，底物范围都非常广泛。具体来说，DHX 的多功能性通过它们转化为氧杂蒽酮和其他复杂结构来证明。