decanoyl fluoride | 334-47-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: decanoyl fluoride
• 英文别名: Decanal, 10-fluoro-
• CAS: 334-47-4
• 化学式: C₁₀H₁₉FO
• 分子量: 174.259
• InChiKey: MXNZLCWRQMCSBF-UHFFFAOYSA-N

物化性质

• 沸点：
  221.7±9.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  decanoyl fluoride 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 neat (no solvent) 为溶剂， 反应 48.0h， 以63%的产率得到1,1,1-三氟癸烷
  参考文献：
  名称：

  Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum deoxofluorinating agent with enhanced thermal stability

  摘要：

  双(2-甲氧乙基)氨基硫三氟化物（Deoxo-FluorTM）在将醇转化为烷基氟化物、将醛/酮转化为相应的双氟化物，以及将羧酸转化为其三氟甲基衍生物方面有效；它是传统的二烷基氨基硫三氟化物（DAST）脱氧氟化试剂的一个热敏感性较低、适用范围更广的替代品。

  DOI：

  10.1039/a808517j
• 作为产物：
  描述：

  癸醛 在 caesium fluoroxysulphate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以54%的产率得到decanoyl 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

• Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
  作者：Mieko Arisawa、Yui Igarashi、Haruki Kobayashi、Toru Yamada、Kentaro Bando、Takuya Ichikawa、Masahiko Yamaguchi

  DOI：10.1016/j.tet.2011.07.031

  日期：2011.10

  enzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer

  铑/膦配合物催化酰基氟，芳基酯，酰基膦硫化物和硫代酯之间的平衡酰基转移反应。使用合适的共底物来接受杂原子基团将平衡转移到所需的产物上。使用苯甲酰基五氟苯作为氟化物供体，将酰基膦硫化物和芳基酯转化为酰基氟，并使用（4-甲苯基硫代）五氟苯进行硫酯的氟化反应。分别使用二膦二硫化物和二硫化物/三苯基膦将酰氟转化为酰基膦硫化物和硫酯。在三苯基硅烷的存在下，由酰基氟和苯酚获得芳基酯。在铑配合物的存在下，芳基酯，酰基膦硫化物和硫代酯也可以相互转化。这些铑催化的酰基转移反应在中性条件下进行，无需使用酸或碱。羰基铑中间体参与这些反应是由硫代酯和炔烃的羰基硫化反应提示的。
• Friedel–Crafts reactions of acyl trifluoromethanesulfonates and cyclic acylsulfonium cations generated from acyl fluorides
  作者：K.V. Raghavendra Rao、Yannick Vallée

  DOI：10.1016/j.tet.2016.06.029

  日期：2016.7

  Reactive acyl trifluoromethanesulfonates are formed from the reaction of acyl fluorides with trimethylsilyl trifluoromethanesulfonate (TMSOTf). These electrophiles undergo Friedel–Crafts reactions with electron-rich aromatics at room temperature. When a sulfur atom is present at their γ position, their cyclization to acylsulfonium cations is observed and is followed by a rearrangement leading to benzothiepinones

  反应性酰基三氟甲磺酸盐是由酰基氟与三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）反应形成的。这些亲电试剂在室温下与富电子芳族化合物发生Friedel-Crafts反应。当硫原子存在于其γ位置时，观察到它们被环化为酰基ls阳离子，随后发生重排，生成苯并噻吩酮（或二苯并[ b，e ]噻吩酮），产率为40-85％。
• Rapid synthesis of acyl fluorides from carboxylic acids with Cu(O2CCF2SO2F)2
  作者：Bingjun Le、Hao Wu、Xiaojun Hu、Xiumiao Zhou、Yong Guo、Qing-Yun Chen、Chao Liu

  DOI：10.1016/j.tetlet.2020.152624

  日期：2020.12

  operationally simple synthetic methods for acyl fluorides has always been desirable. We report herein a rapid, simple and efficient acyl fluoride synthesis from carboxylic acids with Cu(O2CCF2SO2F)2 as a deoxofluorination reagent. Notably, Cu(O2CCF2SO2F)2 was readily prepared in large scale from inexpensive starting material, and previously used as a good trifluoromethylating reagent.

  酰基氟具有适度的亲电子性，并且在稳定性和反应性之间具有非常好的平衡。在过渡金属催化中，酰基氟作为多用途的构建基体的使用吸引了快速增长的关注，并且最近受到了极大的关注。一直期望开发快速且操作简单的酰基氟合成方法。我们在此报告了一种以Cu（O 2 CCF 2 SO 2 F）2为脱氧氟化剂的羧酸快速，简单和有效的酰氟合成方法。值得注意的是，Cu（O 2 CCF 2 SO 2 F）2 由廉价的起始原料容易地大规模制备，并且先前用作良好的三氟甲基化试剂。
• Organocatalyzed Fluoride Metathesis
  作者：Daniel Mulryan、Andrew J. P. White、Mark R. Crimmin

  DOI：10.1021/acs.orglett.0c03593

  日期：2020.12.4

  A new organocatalyzed fluoride metathesis reaction between fluoroarenes and carbonyl derivatives is reported. The reaction exchanges fluoride (F–) and alternate nucleophiles (OAc–, OCO2R–, SR–, Cl–, CN–, NCS–). The approach provides a conceptually novel route to manipulate the fluorine content of organic molecules. When the fluorination and defluorination steps are combined into a single catalytic

  报道了氟代芳烃和羰基衍生物之间新的有机催化的氟化物复分解反应。将反应交流氟化物（F - ）和亲核试剂替代的（OAC -，OCO 2 - [R -，SR - ，氯-，CN -，NCS - ）。该方法提供了一种概念上新颖的途径来控制有机分子的氟含量。当将氟化和脱氟步骤合并为一个催化循环时，可以实现无副产物且原子效率为100％的反应。
• Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations
  作者：Yi Liu、Cuihan Zhou、Meijing Jiang、Bruce A. Arndtsen

  DOI：10.1021/jacs.2c01951

  日期：2022.6.1

  We describe the development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides from aryl, heteroaryl, alkyl, and functionalized organic halides. Mechanistic analysis suggests that the reaction proceeds via the synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create

  我们描述了从芳基、杂芳基、烷基和官能化有机卤化物合成酰基氟化物的一般钯催化羰基化方法的发展。机理分析表明，反应通过Pd(0) 的可见光光激发的协同组合进行，以诱导氧化加成和配体有利的还原消除。这些共同创造了一个单向催化循环，不受一氧化碳配位的经典效应的抑制。将酰氟的催化形成与其随后的亲核反应相结合，开辟了一种以前所未有的广度进行羰基化反应的方法，包括高度官能化的含羰基产物的组装。