(R)-2-fluorocyclohexanone | 694-82-6

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酮(含烯醇)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-fluorocyclohexanone
• 英文别名: (2R)-2-fluorocyclohexan-1-one
• CAS: 694-82-6
• 化学式: C₆H₉FO
• 分子量: 116.135
• InChiKey: VQYOFTVCYSPHPG-RXMQYKEDSA-N

物化性质

• 沸点：
  111-110 °C/70 mmHg
• 密度：
  1.040 g/mL at 25 °C
• 闪点：
  78°C/17mm

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn,Xi
• 安全说明：
  S26,S36/37,S61
• 危险类别码：
  R22,R36,R52/53,R43
• WGK Germany：
  3
• 海关编码：
  2914700090
• 危险标志：
  GHS07
• 危险性描述：
  H302,H317,H319
• 危险性防范说明：
  P280,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  苯基溴化镁 、 (R)-2-fluorocyclohexanone 以 四氢呋喃 、 乙醚 为溶剂， 以128 mg的产率得到(1R,2R)-2-fluoro-1-phenylcyclohexan-1-ol
  参考文献：
  名称：

  Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

  摘要：

  The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.

  DOI：

  10.1021/ja111163u
• 作为产物：
  描述：

  (R)-3-Cyclohex-1-enyl-4-phenyl-oxazolidin-2-one 在 水 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 N-氟代双苯磺酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (R)-2-fluorocyclohexanone
  参考文献：
  名称：

  通过手性烯酰胺的氟化高度区域和立体选择性合成 α-氟化酰亚胺

  摘要：

  描述了手性烯酰胺的高度π面选择性和区域选择性氟化。该反应涉及使用 N-F 试剂（例如 Selectflu 和N-氟苯磺酰亚胺 [NFSI] ）仅在富电子烯酰胺烯烃上进行对映选择性氟化，同时用水捕获 β-氟亚胺阳离子中间体。所得的N,O -半缩醛可以使用戴斯-马丁高碘烷氧化，从而产生用于合成手性 α-氟酰亚胺和光学富集的 α-氟酮的不对称序列。

  DOI：

  10.1021/ol503591d

文献信息

• Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
  作者：Sudipta Ponra、Jianping Yang、Sutthichat Kerdphon、Pher G. Andersson

  DOI：10.1002/anie.201903954

  日期：2019.7

  chiral fluorine‐containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is based on the iridium‐catalyzed asymmetric hydrogenation of trisubstituted alkenyl fluorides. This catalytic asymmetric process enables the synthesis of chiral fluorine molecules with or without carbonyl substitution

  合成手性含氟分子的新通用方法的开发对于一些科学学科而言非常重要。我们在此公开了一种简单的制备手性有机氟分子的方法，该方法基于铱取代的三取代链烯基氟化物的铱催化不对称氢化。该催化不对称过程使得能够合成具有或不具有羰基取代的手性氟分子。由于氮杂双环噻唑-膦铱催化剂具有可调节的空间和电子特性，因此可以优化该立体选择性反应，发现该立体选择性反应可与具有各种官能团的各种芳族，脂族和杂环体系兼容，从而提供了非常理想的产品具有优异的收率和对映选择性。
• Diastereoselective Electrophilic Fluorination of Enantiopure α-Silylketones Using N-Fluoro-benzosulfonimide: Regio- and Enantioselective Synthesis of α-Fluoroketones
  作者：Dieter Enders、Sophie Faure、Marcus Potthoff、Jan Runsink

  DOI：10.1055/s-2001-18449

  日期：——

  synthesized in good yields and high enantiomeric excesses (ee = 87– 96%) from the corresponding simple cyclic and acyclic ketone precursors. The procedure involves a regioand diastereoselective electrophilic fluorination of enantiopure -silylketones 2 (de = 37– 98%) using commercially available N-fluorobenzosulfonimide as fluorinating agent, followed by a racemization–free cleavage of the silyl directing

  Synthesis 2001, No. 15, 12 11 2001。文章标识符：1437-210X,E;2001,0,15,2307,2319,ftx,en;Z10001SS.pdf。© Georg Thieme Verlag Stuttgart · 纽约 ISSN 0039-7881 摘要： - 氟代酮 6 由相应的简单环状和非环状酮前体以高产率和高对映体过量（ee = 87–96%）合成。该过程包括使用市售的 N-氟苯磺酰亚胺作为氟化剂对对映体纯-甲硅烷基酮 2 (de = 37–98%) 进行区域和非对映选择性亲电氟化，然后以几乎定量的产率对甲硅烷基导向基团进行无消旋化裂解。
• Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst
  作者：K SZORI、G SZOLLOSI、M BARTOK

  DOI：10.1016/j.jcat.2006.09.006

  日期：2006.12.10

  The first example of enantioselective heterogeneous catalytic hydrogenation of an a-fluoro ketone is reported. The hydrogenation of racemic 2-fluorocyclohexanone over cinchonidine- or methoxycinchonidine-modified Pt/Al2O3 resulted in diastereoselective and enantioselective formation of the cis-(1R, 2S)-2-fluorocyclohexanol. Due to the preferential hydrogenation of the S enantiomer, the kinetic resolution of the substrate was possible; the unreacted R enantiomer was accumulated in the reaction mixture. Under our experimental conditions, high diastereoselectivities (up to 85%) and good enantioselectivities (up to 59%) were obtained, demonstrating that activation of a ketone by a single alpha fluorine atom is efficient for obtaining enantiodiscrimination in this heterogeneous catalytic system. (c) 2006 Elsevier Inc. All rights reserved.
• Regio- and Enantioselective Synthesis ofα-Fluoroketones by Electrophilic Fluorination ofα-Silylketone Enolates withN-Fluorobenzosulfonimide
  作者：Dieter Enders、Marcus Potthoff、Gerhard Raabe、Jan Runsink

  DOI：10.1002/anie.199723621

  日期：1997.11.14
• Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
  作者：Piotr Kwiatkowski、Teresa D. Beeson、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja111163u

  日期：2011.2.16

  The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.