(S)-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: (S)-2-fluorocyclohexanone
• 英文别名: 2-fluorocyclohexan-1-one；2e,-2-Fluorcyclohexanon；(2S)-2-Fluorocyclohexan-1-one
• CAS: 694-82-6
• 化学式: C₆H₉FO
• 分子量: 116.135
• InChiKey: VQYOFTVCYSPHPG-YFKPBYRVSA-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

• 作为产物：
  描述：

  2-氟-环己醇 在 Pt/Al₂O₃ jones' reagent 、 氢气 、 溶剂黄146 、 辛可尼丁 作用下， 以 四氢呋喃 、 丙酮 为溶剂， -0.15~23.85 ℃ 、4.0 MPa 条件下， 生成 (S)-2-fluorocyclohexanone
  参考文献：
  名称：

  Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst

  摘要：

  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.

  DOI：

  10.1016/j.jcat.2006.09.006

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。
• [EN] CHOLINE METABOLISM INHIBITORS<br/>[FR] INHIBITEURS DU MÉTABOLISME DE LA CHOLINE
  申请人：HARVARD COLLEGE

  公开号：WO2020117942A1

  公开（公告）日：2020-06-11

  The present disclosure relates to compounds, compositions and methods for inhibiting choline metabolism, e.g., conversion of choline to trimethylamine. Disclosed herein are compounds, compositions, and methods for inhibiting choline metabolism, e.g., conversion of choline to TMA. Also disclosed herein are compounds, methods and compositions for inhibiting choline metabolism by gut microbiota resulting in reduction in the formation of trimethylamine (TMA) and trimethylamine N-oxide (TMAO).

  本公开涉及抑制胆碱代谢的化合物、组合物和方法，例如抑制胆碱转化为三甲胺的过程。本文披露了用于抑制胆碱代谢的化合物、组合物和方法，例如抑制胆碱转化为TMA。本文还披露了通过肠道微生物抑制胆碱代谢的化合物、方法和组合物，从而减少三甲胺（TMA）和三甲胺N-氧化物（TMAO）的形成。
• 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.
• 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.