9-anthroyl fluoride | 175407-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-anthroyl fluoride
• 英文别名: anthracene-9-carbonyl fluoride
• CAS: 175407-20-2
• 化学式: C₁₅H₉FO
• 分子量: 224.234
• InChiKey: XPRYNDMUQAGJKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  9-anthroyl fluoride 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 96.0h， 生成 1-O-(2-anthroyl)-3-S-(9-anthroyl)-3-sulfanyl-1-hexanol
  参考文献：
  名称：

  使用CD激子手性法对无环2和3硫烷基-1-烷醇进行立体化学分配的一种新的一步策略。

  摘要：

  使用CD激子手性方法描述了一种新的一步策略，用于无环2和3硫烷基-1-烷醇的立体化学分配。使用9-邻苯二甲酸盐生色团将两个官能团衍生化，生成的双符号CD曲线明确地允许从单个CD测量值确定立体化学。使用合成的光学纯的3-硫烷基-1-己醇和2-硫烷基-1-己醇作为模型化合物证明了该新方法的有效性。发达的微型方法也可用于1,2-和1,3-二醇的立体化学分配。据我们所知，这是CD激子手性方法在无环2-和3-硫烷基-1-链烷醇上的首次应用。

  DOI：

  10.1021/jo010768h
• 作为产物：
  描述：

  9-蒽甲酸 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到9-anthroyl fluoride
  参考文献：
  名称：

  来自蓝细菌Nostoc PCC 6720的两个具有无环戊醇侧链的类细菌类胡萝卜素的结构

  摘要：

  从蓝细菌Nostoc PCC 6720中分离出两种细菌杂戊戊醇2和3。通过1 H，13 C-NMR和质谱分析了它们的结构。无环的1,2-和1,2- / 1,3-混合的戊醇侧链的绝对构型通过双色激子偶联的二色性在微克级上测定。还描述了两步衍生化中改进的第一步邻氨基苯甲酸酯化。

  DOI：

  10.1016/0040-4020(96)00013-0

文献信息

• Nickel-catalysed decarbonylative borylation of aroyl fluorides
  作者：Zhenhua Wang、Xiu Wang、Yasushi Nishihara

  DOI：10.1039/c8cc08504h

  日期：——

  The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.

  已经建立了第一个Ni（cod）2 / PPh 3催化剂体系，用于芳酰氟与双（频哪醇）二硼的脱羰基硼酸酯化反应。底物中的多种官能团均具有良好的耐受性。容易获得起始的芳酰氟表明，这些结果可能成为现有脱羰事件的替代方法。
• Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction
  作者：Qiang Chen、Zhenyao Li、Yasushi Nishihara

  DOI：10.1021/acs.orglett.1c04060

  日期：2022.1.14

  In this Letter, the palladium/copper-cocatalyzed arylsilylation of internal alkynes with acyl fluorides and silylboranes is described. This is the first example in which acyl fluorides have been utilized for the three-component coupling reaction via decarbonylation, yielding a variety of tetrasubstituted alkenylsilanes in moderate to good yields.

  在这封信中，描述了内部炔烃与酰基氟和甲硅烷基硼烷的钯/铜共催化芳基硅烷化。这是第一个使用酰基氟通过脱羰基进行三组分偶联反应的例子，以中等至良好的收率产生各种四取代的烯基硅烷。
• Phosphine‐Catalyzed Acyl‐Group Exchange Reaction of Carboxylic Acids and an Aroyl Fluoride
  作者：Hiroyuki Hattori、Kento Ishida、Yohei Ogiwara、Norio Sakai

  DOI：10.1002/ejoc.202201118

  日期：2022.12.12

  A phosphine-catalyzed acyl-group exchange reaction between carboxylic acids and an aroyl fluoride has been developed. A variety of acyl fluorides are directly obtained from carboxylic acids through a catalytic system composed of tricyclohexylphosphine (PCy3) and 2,6-difluorobenzoyl fluoride as a novel deoxyfluorination reagent.

  已经开发了膦催化的羧酸和芳酰氟之间的酰基交换反应。以三环己基膦（PCy 3）和2,6-二氟苯甲酰氟为新型脱氧试剂，通过催化体系由羧酸直接制得多种酰基氟。
• Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C–OMe Bond Cleavage under Metal-Free Conditions
  作者：Xiu Wang、Zhenhua Wang、Takumi Ishida、Yasushi Nishihara

  DOI：10.1021/acs.joc.0c00640

  日期：2020.6.5

  Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp(2))-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.
• Synthesis and inclusion ability of anthracene appended β-cyclodextrins: unexpected effect of triazole linker
  作者：Isabelle Mallard、David Landy、Nadia Bouchemal、Sophie Fourmentin

  DOI：10.1016/j.carres.2010.09.031

  日期：2011.1

  A new fluorescent beta-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole. (C) 2010 Elsevier Ltd. All rights reserved.