2-乙基-2,4,4,4-四氟-3-氧代丁酸酯 | 685-69-8

• 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
• 中文名称: 2-乙基-2,4,4,4-四氟-3-氧代丁酸酯
• 英文名称: ethyl 2,4,4,4-tetrafluoro-3-oxobutanoate
• 英文别名: ethyl 3-oxo-2,4,4,4-tetrafluoro-butyrate
• CAS: 685-69-8
• 化学式: C₆H₆F₄O₃
• mdl: MFCD09839527
• 分子量: 202.105
• InChiKey: JQGQFCBRPKXRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-乙基-2,4,4,4-四氟-3-氧代丁酸酯 在 正丁基锂 作用下， 以 正己烷 为溶剂， 生成
  参考文献：
  名称：

  含四氟酮和乙酰乙酸酯：合成和机理研究

  摘要：

  将三氟乙酸三甲基甲硅烷基酯加入到 α-氟苄基膦酸酯 (3) 或二异丙基(氟代甲氧基甲基) 膦酸酯 (9) 的碳负离子中，形成相应的中间体 [CF 3 C(O)CFPh] - Li + (10) 和 [CF 3 C( O)CFCO 2 Et]Li + (11)，分别。随后对 10 和 11 进行质子化、烷基化或烯丙基化，得到三氟甲基氟苄基酮 12 和 2,4,4,4-四氟乙酰乙酸乙酯 13。基于所得结果，提出了一种合理的机理。

  DOI：

  10.1002/jccs.200700107
• 作为产物：
  描述：

  2-(Diethoxy-phosphoryl)-2,4,4,4-tetrafluoro-3-oxo-butyric acid ethyl ester 在 碳酸氢钠 作用下， 反应 6.0h， 生成 2-乙基-2,4,4,4-四氟-3-氧代丁酸酯
  参考文献：
  名称：

  Acylation of fluorocarbethoxy-substituted ylides: a simple and general route to .alpha.-fluoro .beta.-keto esters

  摘要：

  (Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salts 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields. The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides. Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt. Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts. However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with R(F)COCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives R(F)COCFHCOOEt.

  DOI：

  10.1021/jo00001a052

文献信息

• APPLICATION OF FLUOROCARBETHOXY-SUBSTITUTED PHOSPHONATE: A FACILE ENTRY TO SUBSTITUTED 2-FLUORO-3-OXOESTERS
  作者：Hou-Jen Tsai

  DOI：10.1080/10426509708043541

  日期：1997.7.1

  Abstract Diethyl(fluorocarbethoxymethyl)phosphonate 1a or diisopropyl(fluorocarbethoxymethyl)phosphonate 1b, prepared from triethyl phosphite or triisopropyl phosphite with ethyl bromofluoroacetate, react with n-butyllithium in THF to give the corresponding phosphonate carbanions [(RO)2P(O)CFCO2Et]−Li+ 2a (R=Et) and 2b (R=i-Pr). Addition of trimethylsilyltrifluoroacetate CF3C(O)OSiMe3 to a THF solution

  摘要 由亚磷酸三乙酯或亚磷酸三异丙酯与溴氟乙酸乙酯制备的二乙基（氟碳乙氧基甲基）膦酸酯 1a 或二异丙基（氟碳乙氧基甲基）膦酸酯 1b 与正丁基锂在 THF 中反应得到相应的膦酸酯碳负离子 [(RO)2P(O)CFCO2Et]- Li+ 2a (R=Et) 和 2b (R=i-Pr)。将三甲基甲硅烷基三氟乙酸酯 CF3C(O)OSiMe3 添加到膦酸酯碳负离子的 THF 溶液中，形成三氟乙酰氟乙酸乙酯 [CF3C(O)CFCO2Et]-Li+3 的烯醇化物。随后烯醇化物的质子化、烷基化或烯丙基化得到取代的 2,4,4,4 -四氟-3-氧代酯 CF3C(O)CFR1CO2Et 10
• One-Pot Reactions for Modular Synthesis of Polysubstituted and Fused Pyridines
  作者：Zhidong Song、Xin Huang、Wenbin Yi、Wei Zhang

  DOI：10.1021/acs.orglett.6b02883

  日期：2016.11.4

  3-dicarbonyl-initiated one-pot Michael addition/[5 + 1] annulation/dehydrofluorinative aromatization reaction sequence is introduced for regioselective synthesis of di-, tri-, tetra-, and pentasubstituted pyridines as well as fused pyridines. This simple and modular synthesis is performed using readily available starting materials and under transition-metal catalyst-free conditions.

  引入2-氟-1,3-二羰基引发的一锅迈克尔加成反应/ [5 +1]环化/脱氟化氢芳构化反应顺序，用于区域选择性合成二，三，四和五取代的吡啶以及吡啶。使用容易获得的原料并在无过渡金属的条件下进行这种简单而模块化的合成。
• Herbicidal heterocyclic compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US04812164A1

  公开（公告）日：1989-03-14

  The invention is concerned with novel C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl and C.sub.3 or 4 -alkynyl enol ethers of 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X are as defined in the specification, their manufacture, weed control compositions which contain such enol ethers as the active substance and the use of the active substances or compositions for the control of weeds. The invention is also concerned with certain novel intermediates, some of which possess herbicidal activity, and with weed control compositions containing such active substances.

  这项发明涉及新颖的3-芳基尿嘧啶的C.sub.1-4-烷基，C.sub.2-4-烯基和C.sub.3或4-炔基烯醇醚，其化学式如下所示：其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5和X如规范中定义，它们的制造，含有这种烯醇醚作为活性物质的除草剂组合物，以及利用这些活性物质或组合物来控制杂草。该发明还涉及某些新颖的中间体，其中一些具有除草活性，并且含有这种活性物质的除草剂组合物。
• 3-(5-carboxy-4-substituted-phenyl)-(thio)uracil-esters and salts
  申请人：Hoffmann-La Roche Inc.

  公开号：US04746352A1

  公开（公告）日：1988-05-24

  The disclosure is concerned with novel 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the significances given in the description, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as active ingredients and the use of the active ingredients or compositions for the control of weeds. The disclosure also concerns certain herbicidally active starting materials and weed control compositions containing these as active ingredients.

  本公开涉及新颖的3-芳基尿嘧啶，其化学式为##STR1##其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和X的含义如描述中所示，以及它们的盐和制备方法，含有这些化合物作为活性成分的除草剂组合物，以及利用这些活性成分或组合物来控制杂草。本公开还涉及某些具有除草活性的起始材料和含有这些起始材料作为活性成分的除草剂组合物。
• One‐Pot Mannich, Aza‐Wittig and Dehydrofluorinative Aromatization Reactions for Direct Synthesis of 2,3‐Disubstituted 4‐Aminoquinolines
  作者：Xiaofeng Zhang、Xiaoming Ma、Weiqi Qiu、JohnMark Awad、Jason Evans、Wei Zhang

  DOI：10.1002/adsc.202000734

  日期：2020.12.8

  One‐pot synthesis of 2,3‐disubstituted 4‐aminoquinolines is developed through a three‐component reaction of 2‐azidobenzaldehydes, α‐fluoro‐β‐ketoesters and amines involving cascade Mannich, aza‐Wittig and dehydrofluorinative aromatization. The method is applicable to other functionalized quinolines. It is a pot, atom and step economy (PASE) synthesis of biologically interesting 4‐aminoquinolines relevant

  通过2-叠氮苯甲醛，α-氟-β-酮酸酯和胺的三组分反应（包括级联曼尼希，氮杂-维蒂希和脱氟化氢芳构化）开发了2，3-二取代的4-氨基喹啉的一锅合成方法。该方法适用于其他官能化喹啉。这是一种与羟氯喹和氯喹相关的，具有生物学意义的4-氨基喹啉的锅，原子和步经济（PASE）合成。