Ethyl 2-chloro-2-fluoroacetoacetate | 135664-26-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Ethyl 2-chloro-2-fluoroacetoacetate
• 英文别名: ethyl 2-chloro-2-fluoro-3-oxobutanoate
• CAS: 135664-26-5
• 化学式: C₆H₈ClFO₃
• 分子量: 182.579
• InChiKey: VSGIDAWRTVCNLF-UHFFFAOYSA-N

物化性质

• 沸点：
  184.5±35.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯乙酰乙酸乙酯 在 甲酸 、 fluorine 作用下， 以62%的产率得到Ethyl 2-chloro-2-fluoroacetoacetate
  参考文献：
  名称：

  Microreactors for elemental fluorine

  摘要：

  一种微反应器已被设计用于与元素氟结合使用，既用于选择性氟化，也用于有机化合物的全氟化。

  DOI：

  10.1039/a901473j

文献信息

• 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。
• Reactions of trifluoroamine oxide: a new method for selective fluorination of 1,3-diketones and β-ketoesters
  作者：Om D Gupta、Jean'ne M Shreeve

  DOI：10.1016/s0040-4039(03)00467-2

  日期：2003.3

  Fluorination of 1,3-diketones and β-ketoesters with trifluoroamine oxide in the presence of tetrabutylammonium hydroxide (TBAH) provides a one step route to mono- and difluoro-products selectively fluorinated at the α-position in good yields.

  在氢氧化四丁铵（TBAH）存在下，用三氟氧化胺氟化1,3-二酮和β-酮​​酸酯提供了一种一步路线，以高收率选择性地在α位氟化的单氟和二氟产品。
• Elemental fluorine. Part 9
  作者：Richard D. Chambers、John Hutchinson

  DOI：10.1016/s0022-1139(98)00254-1

  日期：1998.10

  Catalysis of the reaction between fluorine and a range of 2-substituted carbonyl compounds has been investigated. Most notably, the preparation of diethyl-2-fluoromalonate has been achieved in high yield by fluorination of diethylmalonate in the presence of hydrated copper nitrate. Reactions between fluorine and carbanions derived from 2-substituted carbonyl compounds, including phosphonates, sulphones

  已经研究了氟与一定范围的2-取代的羰基化合物之间反应的催化作用。最值得注意的是，通过在水合硝酸铜存在下氟化二乙基丙二酸二乙酯，可以高产率地制备2-氟丙二酸二乙酯。还讨论了氟与衍生自2-取代羰基化合物（包括膦酸酯，砜和腈）的碳负离子之间的反应。
• N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the .alpha.-fluorination of functionalized carbonyl compounds
  作者：Giuseppe Resnati、Darryl D. DesMarteau

  DOI：10.1021/jo00016a022

  日期：1991.8

  The N-fluorobis[(trifluoromethyl)sulfonyl]imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones. The corresponding alpha-fluorocarbonyl compounds have been obtained in good yields. The alpha-fluorination of beta-diesters, beta-diamides, beta-keto esters, and beta-diketones has been performed either on the neutral compounds or on the metal enolates. In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields. Also some alpha-keto esters and acids have been selectively monofluorinated in the beta-position by simple treatment of the neutral compound with 1.
• CATALYSED FLUORINATION OF CARBONYL COMPOUNDS
  申请人：F2 Chemicals Ltd.

  公开号：EP0996606A1

  公开（公告）日：2000-05-03