3-fluorophenyl ethyl ketene | 1241946-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-fluorophenyl ethyl ketene
• CAS: 1241946-62-2
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: KHLWOYQSDONLRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-fluorophenyl ethyl ketene 、 2-亚硝基吡啶 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 diphenylphosphino-phenyl-ferrocenyl-ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到4-ethyl-4-(3-fluorophenyl)-2-pyridin-2-yl-1,2-oxazetidin-3-one
  参考文献：
  名称：

  铜催化的2-亚硝基吡啶与酮丁烯的对映选择性[2 + 2]环加成反应

  摘要：

  铜（I）催化的各种烯酮与[2- +亚硝基吡啶]的[2 + 2]环加成反应可提供合成上非常有价值的1,2-氧杂氮杂环丁烷-3-酮，并具有良好的对映选择性。热的未催化过程提供了不稳定的区域异构的恶唑烷酮。密度泛函理论（DFT）计算提供了证据，表明该反应是通过一致的[2 + 2]环加成途径发生的。

  DOI：

  10.1002/adsc.201000153
• 作为产物：
  描述：

  C₁₀H₁₀ClFO 在 二甲基十二/十四烷基叔胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-fluorophenyl ethyl ketene
  参考文献：
  名称：

  通过有机催化的氨甲基化形成全碳四元立体中心：精确获得β2,2-氨基酸。

  摘要：

  的β不对称合成2,2- α-氨基酸保留在有机合成一个巨大的挑战。这里有稳定且容易获得的N，O-缩醛烯酮的一种新颖的对映选择性有机催化氨基甲基报道，提供β 2,2-氨基酯轴承在高对映体比率的全碳季立体中心具有手性磷酸催化量。通常，这种转变可能是通过不对称的反阴离子导向催化进行的。其结果是，一个简洁，实用，和原子的经济朝向快速访问β协议2,2 α-氨基酸已经研制成功。

  DOI：

  10.1002/anie.202009892

文献信息

• Asymmetric Synthesis of Hydroindoles via Desymmetrizing [3+2] Annulation of p-Quinamines and Arylalkylketenes
  作者：Qianping Chen、Yan Zhang、Yanji Song、Yang Zhang、Zhishan Su、Xiaoming Feng、Xiaohua Liu

  DOI：10.1021/acs.orglett.4c00780

  日期：2024.4.26

  The asymmetric desymmetrizing [3+2] annulation reaction of p-quinamines and arylalkylketenes to synthesize hydroindoles was realized. Catalyzed by chiral bisguanidinium hemisalt via multiple hydrogen bond interactions, enantiomerically enriched products with reversal of diastereoselectivity in comparison with the racemic version were afforded in good yields under mild reaction conditions. Diaryl-substituted

  实现了对奎胺与芳烷基乙烯酮的不对称去对称[3+2]环化反应合成氢吲哚。在手性双胍半盐的多重氢键相互作用的催化下，与外消旋形式相比，对映体富集的产物具有相反的非对映选择性，在温和的反应条件下以良好的产率提供。二芳基取代的氢吲哚也可以进行弗里德尔-克来福特类型的加成，得到更复杂的多环。密度泛函理论计算表明，对映选择性和非对映选择性源于不同的氢键结合方式。
• Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones
  作者：Xiaoyu Hao、Xiaohua Liu、Wei Li、Fei Tan、Yangyang Chu、Xiaohu Zhao、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol4031217

  日期：2014.1.3

  Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.
• Competitive Activity-Based Protein Profiling Identifies Aza-β-Lactams as a Versatile Chemotype for Serine Hydrolase Inhibition
  作者：Andrea M. Zuhl、Justin T. Mohr、Daniel A. Bachovchin、Sherry Niessen、Ku-Lung Hsu、Jacob M. Berlin、Maximilian Dochnahl、María P. López-Alberca、Gregory C. Fu、Benjamin F. Cravatt

  DOI：10.1021/ja300799t

  日期：2012.3.21

  Serine hydrolases are one of the largest and most diverse enzyme classes in Nature. Most serine hydrolases lack selective inhibitors, which are valuable probes for assigning functions to these enzymes. We recently discovered a set of aza-beta-lactams (ABLs) that act as potent and selective inhibitors of the mammalian serine hydrolase protein-phosphatase methylesterase-1 (PME-1). The ABLs inactivate PME-1 by covalent acylation of the enzyme's serine nucleophile, suggesting that they could offer a general scaffold for serine hydrolase inhibitor discovery. Here, we have tested this hypothesis by screening ABLs more broadly against cell and tissue proteomes by competitive activity-based protein profiling (ABPP), leading to the discovery of lead inhibitors for several serine hydrolases, including the uncharacterized enzyme alpha,beta-hydrolase domain-containing 10 (ABHD10). ABPP-guided medicinal chemistry yielded a compound ABL303 that potently (IC50 approximate to 30 nM) and selectively inactivated ABHD10 in vitro and in living cells. A comparison of optimized inhibitors for PME-1 and ABHD10 indicates that modest structural changes that alter steric bulk can tailor the ABL to selectively react with distinct, distantly related serine hydrolases. Our findings, taken together, designate the ABL as a versatile reactive group for creating first-in-class serine hydrolase inhibitors.
• Ligand Control of Diastereodivergency in Asymmetric Inverse Electron Demand Diels–Alder Reaction
  作者：Xiaoyu Hao、Lili Lin、Fei Tan、Chengkai Yin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acscatal.5b01719

  日期：2015.10.2

  A diastereodivergent direct catalytic asymmetric inverse electron demand Diels-Alder reaction between ketenes and 3-alkylenyloxindoles was accomplished by using chiral N,N'-dioxide/gadolinium complexes. By adjusting only the substituents of the ligand and retaining other catalysis conditions, both syn- and anti-indole-fused dihydropyranones bearing two vicinal stereogenic centers were obtained in high yields with excellent ee values. Thus, by changing the configuration of the chiral ligands, all stereoisomers could be obtained from the same set of starting materials.
• [EN] AlphaZetaAlpha-beta-LACTAM COMPOUNDS AND METHODS OF USING<br/>[FR] COMPOSÉS AZA-Beta-LACTAMES ET PROCÉDÉS D'UTILISATION
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2013152272A1

  公开（公告）日：2013-10-10

  The invention is directed to methods of modulation of serine hydrolase ABHD10, which can be selective with respect to other serine hydrolases such as PME-1. The compounds of the invention, or compounds useful in practice of a method of the invention, are aza-β-lactams, of which the (R)-enantiomer is preferred, for modulation of ABHD10. Methods of preparation are provided comprising the cycloaddition of dialkylazodicarboxylates with ketenes using the catalyst PPY*. The invention provides methods of treatment of conditions in patients for which modulation of ABHD10 is indicated, including pain, inflammation, metabolic disorders, solid tumors, or obesity.