2-乙酰基-2-氟环己壬 | 74279-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基-2-氟环己壬
• 英文名称: 2-fluoro-2-acetylcyclohexanone
• 英文别名: 2-acetyl-2-fluorocyclohexanone；2-acetyl-2-fluorocyclohexan-1-one
• CAS: 74279-75-7
• 化学式: C₈H₁₁FO₂
• mdl: MFCD00215827
• 分子量: 158.173
• InChiKey: UDAGURMNBXWXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基环己酮 在 碘苯二乙酸 、 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以68%的产率得到2-乙酰基-2-氟环己壬
  参考文献：
  名称：

  使用 PhI(OAc)2 介导的亲核氟化物对 1,3-二羰基化合物的表观亲电氟化

  摘要：

  报道了使用 Et3N·3HF 作为亲核氟化物源的 1,3-二羰基化合物的表观亲电氟化。该反应需要 PhI(OAc)2 作为氧化剂，可以在标准实验室玻璃器皿中安全进行。在某些情况下，观察到了与 Selectfluor 相比的替代选择性。这种方法可以减少我们对难以处理的氟气和源自元素氟的昂贵亲电子氟化剂的依赖。介绍了与活性氟化物质和氟化物/乙酸盐交换相关的机理分析。

  DOI：

  10.1002/ejoc.201500370

文献信息

• Electrophilic fluorination with N,N′-difluoro-2,2′-bipyridinium salt and elemental fluorine
  作者：Kenji Adachi、Yutaka Ohira、Ginjiro Tomizawa、Sumi Ishihara、Satoshi Oishi

  DOI：10.1016/s0022-1139(02)00327-5

  日期：2003.4

  (MEC-31) was shown to be a highly reactive electrophilic fluorinating agent with the highest effective fluorine content in its class. We have developed the perfect recycled fluorination system with MEC-31 for the lower-cost industrial fluorination and for an environment. MEC-31 can be completely recycled including the counter-anion. We found the fluorination of 2-naphthol in liquid CO2 with MEC-31 in

  N，N′-二氟-2，2′-联吡啶双（四氟硼酸酯）（MEC-31）被证明是一种高反应性的亲电氟化剂，具有同类中最高的有效氟含量。我们已经开发出带有MEC-31的完美的循环氟化系统，可用于低成本工业氟化和环境。MEC-31可以完全回收，包括抗衡阴离子。我们发现，在催化量的NaOTf存在下，用MEC-31在液态CO 2中氟化2-萘酚是定量进行的，而没有副产物的产生。
• Direct fluorination of 1,3-dicarbonyl compounds
  作者：Richard D. Chambers、Martin P. Greenhall、John Hutchinson

  DOI：10.1016/0040-4020(95)00883-a

  日期：1996.1

  In acid media, 1,3-diketones and 1,3-ketoesters can be fluorinated in high yield and often with high conversion mainly to the corresponding 2-fluoro- compounds. Diesters such as diethyl malonate do not react with fluorine under the same reaction conditions. The mechanism of these reactions has been investigated and while the identity of the electrophilic fluorinating species is uncertain, we believe

  在酸性介质中，1,3-二酮和1,3-酮酸酯可以高产率地氟化，并且通常主要以高转化率转化为相应的2-氟化合物。在相同的反应条件下，丙二酸二乙酯等二酯不会与氟反应。已经研究了这些反应的机理，并且尽管亲电性氟化物质的身份尚不确定，但我们认为已经理解了反应途径的基本特征。
• Solvent-free fluorination of organic compounds using N–F reagents
  作者：Gaj Stavber、Marko Zupan、Stojan Stavber

  DOI：10.1016/j.tetlet.2007.02.077

  日期：2007.4

  Efficient fluorination of 1,3-dicarbonyl compounds, enol acetates of aromatic ketones, and activated aromatic compounds was achieved under solvent-free conditions using Selectfluor™ F–TEDA–BF4 or Accufluor™ NFSi.

  使用Selectfluor™F–TEDA–BF 4或Accufluor™NFSi，可在无溶剂条件下有效地氟化1,3-二羰基化合物，芳族酮的烯醇乙酸酯和活化的芳族化合物。
• Self‐Sustaining Fluorination of Active Methylene Compounds and High‐Yielding Fluorination of Highly Basic Aryl and Alkenyl Lithium Species with a Sterically Hindered <i>N</i> ‐Fluorosulfonamide Reagent
  作者：Yuhao Yang、Gerald B. Hammond、Teruo Umemoto

  DOI：10.1002/anie.202211688

  日期：2022.10.24

  By developing a sterically hindered fluorinating agent, N-fluoro-N-(tert-butyl)-tert-butanesulfonamide (NFBB), we discovered a conceptually novel base-catalyzed, self-sustaining fluorination of active methylene compounds and achieved an unprecedented high-yield fluorination of highly basic (hetero)aryl and alkenyl lithium species.

  通过开发空间位阻氟化剂N-氟-N- (叔丁基)-叔丁磺酰胺(NFBB)，我们发现了一种概念性新颖的碱催化、活性亚甲基化合物自持氟化反应，并实现了前所未有的高产率。产生高碱性（杂）芳基和烯基锂物种的氟化。
• Highly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System
  作者：Teruo Umemoto、Ginjiro Tomizawa

  DOI：10.1021/jo00125a049

  日期：1995.10

  A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium-2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium-3- and -4-sulfonates 3 and 4 were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. Thus, phenol, naphthol, phenylurethane, and the trimethylsilyl ether of phenol were exclusively or highly selectively fluorinated at the o-position with 2f-h. Conjugated enol trialkylsilyl ethers of a steroid were regioselectively fluorinated at the 6-position with moderately powerful 2b-e. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive B-fluorination was achieved. Preferential beta-stereoselective fluorination at the 6-position was observed. N-Fluoropyridinium-2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.