pentafluorobenzoyl fluoride | 1478-07-5

• 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: pentafluorobenzoyl fluoride
• 英文别名: Pentafluorbenzoylfluorid；2,3,4,5,6-pentafluorobenzoyl fluoride
• CAS: 1478-07-5
• 化学式: C₇F₆O
• 分子量: 214.067
• InChiKey: UJIMKBIIBQNAOC-UHFFFAOYSA-N

物化性质

• 沸点：
  140-141 °C
• 密度：
  1.634±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pentafluorobenzoyl fluoride 在 盐酸 、 sodium borohydrid 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 五氟苯甲醇
  参考文献：
  名称：

  Process for the preparation of halogenated benzoyl fluorides

  摘要：

  一种制备卤代苯甲酰氟的方法，包括将式为##STR1##的卤代苯三氟化物与至少一种硫化合物接触，其中m和n分别独立地表示0到5的整数，m和n的和为5，所述硫化合物的式为##STR2##，其中X表示氟、氯或羟基，Y表示羟基，或者X和Y一起表示通过双键与硫原子连接的氧原子，在升高温度下反应后，从反应混合物中以##STR3##的化合物形式去除硫化合物，其中X具有给定的含义，Hal表示氟或氯，反应产物进一步在升高温度和增加压力下与氟化钾反应。

  公开号：

  US04330366A1
• 作为产物：
  描述：

  五氟苯甲醛 在 caesium fluoroxysulphate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以12.5%的产率得到pentafluorobenzoyl fluoride
  参考文献：
  名称：

  Reactions of aldehydes with cesium fluoroxysulfate

  摘要：

  Various aromatic and aliphatic aldehydes reacted at 35-40-degrees-C in CH3CN with CsSO4F giving acid fluorides in a good yield. In some cases formation of fluorohydrocarbons was also observed. Hammett correlation analysis of the transformation of various substituted benzaldehydes (p-OCH3, p-CH3, p-F, p-CF3, m-NO2) gave the reaction constant rho+ = -0.38. Solvent polarity strongly influenced the conversion of aldehydes into acid fluorides, being in acetonitrile almost quantitative and completely halted in CH2Cl2, n-hexane, or tetrahydrofuran. The presence of nitrobenzene, often used as a radical scavenger, considerably reduced the acid fluoride formation. Based on experimental observations was concluded that the main intermediates involved in the conversion of aldehydes into acid fluorides With CsSO4F must be of a radical nature.

  DOI：

  10.1021/jo00046a013

文献信息

• Formation and reactions of carbanions from α-substituted perfluoroacyl fluorides
  作者：L.S. Chen、K.C. Eapen

  DOI：10.1016/s0022-1139(00)81257-9

  日期：1991.11

  acetonitrile with alkali metal fluorides. Other products identified in hydrolyzed reaction mixtures include perfluoroolefins and monohydroperfluoro compounds. A mechanism involving the formation of a carbanion intermediate is proposed. Evidence for the formation of carbanions has been obtained by carrying out the reaction in the presence of bromine and also in the presence of other substrates.

  在乙腈中与碱金属氟化物一起回流时，脂肪族α-取代的全氟酰基氟以低至中等的产率转化为受阻酮。在水解反应混合物中鉴定出的其他产物包括全氟烯烃和单氢全氟化合物。提出了涉及碳负离子中间体形成的机理。通过在溴的存在下以及在其他底物的存在下进行反应，获得了形成碳负离子的证据。
• Visible‐Light‐Induced Cycloaddition of α‐Ketoacylsilanes with Imines: Facile Access to β‐Lactams
  作者：Jian‐Heng Ye、Peter Bellotti、Tiffany O. Paulisch、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1002/anie.202102451

  日期：2021.6.7

  report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory

  我们报告了由 α-酮酰基硅烷和亚胺合成 β-内酰胺，该合成通过正式的 [2+2] 光化学环加成反应进行，并原位生成甲硅烷氧基乙烯酮。这种温和且操作简单的反应以原子经济方式进行，底物范围广泛，包括醛亚胺、酮亚胺、腙和稠氮杂环，在大多数情况下提供各种具有令人满意的非对映选择性的重要 β-内酰胺。该反应还具有良好的官能团耐受性、易于扩展和产品多样化。实验和计算研究表明，α-酮酰基硅烷可以通过 1,3 硅转移到远端羰基作为光化学前体。
• Hydrogen Bond Directed Photocatalytic Hydrodefluorination and Methods of Use Thereof
  申请人：The Board of Regents for Oklahoma State University

  公开号：US20200399196A1

  公开（公告）日：2020-12-24

  Methods of synthesizing compounds comprising fluorinated aryl groups are disclosed, wherein said methods utilize hydrogen bond directed photocatalytic hydrodefluorination.

  揭示了合成含氟芳基化合物的方法，其中所述方法利用氢键定向的光催化脱氟化反应。
• COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR
  申请人：HUMAN BIOMOLECULAR RESEARCH INSTITUTE

  公开号：US20160038641A1

  公开（公告）日：2016-02-11

  Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of osteogenic materials that were administered to cells or co-cultured with cells are represented by compounds of Formula II, IV, and VI independently or preferably in combination with a matrix to afford bone cells. Small molecule-stimulated cells were also combined with a matrix, placed with a cellular adhesive or material carrier and implanted to a site in an animal for bone repair. Matrix pretreated with compounds of Formula II, IV, and VI were also used to cause cells to migrate to the matrix that is of use for therapeutic purposes.

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。
• New method of preparation of fluoro compounds via utilisation of ammonium and phosphonium perfluorocyclobutane ylides as fluorination reagents
  作者：Sergej V. Pasenok、Marijn E. de Roos、Wolfgang K. Appel

  DOI：10.1016/0040-4020(96)00019-1

  日期：1996.2

  Ammonium- and phosphoniumperfluorocyclobutane ylides (7–11), easily prepared from perfluorocyclobutene (1) and tertiary amines (2–4) or phosphines (5,6), smoothly react with primary or secondary alcohols (12–18) and carboxylic acids (19,20) with formation of alkyl fluorides (21–26) or acyl fluorides (27,28), respectively. A mechanism for the reaction is proposed.

  由全氟环丁烯（1）和叔胺（2-4）或膦（5,6）容易制得的全氟环丁烷铵盐和磷鎓盐（7-11），可以与伯醇或仲醇（12-18）和羧酸（平稳地）反应19,20）分别形成烷基氟化物（21–26）或酰基氟（27,28）。提出了反应机理。