ethyl 2-fluoro-3-oxo-3-tert-butylpropanoate | 118460-47-2

• 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-fluoro-3-oxo-3-tert-butylpropanoate
• 英文别名: ethyl 4,4-dimethyl-2-fluoro-3-oxopentanoate；ethyl 2-fluoro-4,4-dimethyl-3-oxopentanoate
• CAS: 118460-47-2
• 化学式: C₉H₁₅FO₃
• 分子量: 190.215
• InChiKey: HLQMJVMMMPTQEG-UHFFFAOYSA-N

物化性质

• 沸点：
  56-61 °C(Press: 2 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-fluoro-3-oxo-3-tert-butylpropanoate 在 三氟乙酸 、 N,N-diisopropyldibenzo[d,f][1,3,2]dioxaphosphepin-6-amine 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 二氯甲烷 为溶剂， 反应 19.67h， 生成 ethyl 2-tert-butyl-3-fluoro-5-methylidene-4,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  氟化N-杂环的Pd催化[4 + 2]环化方法

  摘要：

  3-氟和三氟甲硫基哌啶是发现化学的重要组成部分。我们报告了一种简单有效的方法，可访问具有丰富功能的这些化合物的类似物，从而可以通过非对映异构体的高度化学控制对其进行化学选择性衍生化。

  DOI：

  10.1021/acs.orglett.1c00752
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 ethyl 2-fluoro-3-oxo-3-tert-butylpropanoate
  参考文献：
  名称：

  An expedient synthesis of α-fluoro-β-ketoesters

  摘要：

  DOI：

  10.1016/s0040-4039(01)93318-0

文献信息

• Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles
  作者：Xiao Han、Jie Luo、Chen Liu、Yixin Lu

  DOI：10.1039/b823184b

  日期：——

  Organocatalytic asymmetric Michael reactions of fluorinated nucleophiles with nitroolefins catalyzed by Cinchona alkaloid-derived thiourea catalysts generated the desired Michael products containing vicinal fluorinated quaternary and tertiary chiral centers with exceptional enantioselectivity.

  由金鸡纳生物碱衍生的硫脲催化剂催化的氟化亲核试剂与硝基烯烃的有机催化不对称迈克尔反应生成了所需的迈克尔产物，该产物含有邻位氟化的季铵和叔手性中心，并具有出色的对映选择性。
• Acylation of fluorocarbethoxy-substituted ylides: a simple and general route to .alpha.-fluoro .beta.-keto esters
  作者：Alagappan Thenappan、Donald J. Burton

  DOI：10.1021/jo00001a052

  日期：1991.1

  (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.
• Oxidation of fluoroalkyl-substituted carbinols by the Dess-Martin reagent
  作者：Russell J. Linderman、David M. Graves

  DOI：10.1021/jo00264a029

  日期：1989.2
• Consecutive catalytic electrophilic fluorination/amination of β-keto esters: toward α-fluoro-α-amino acids?
  作者：Dominique Pascal Huber、Kyrill Stanek、Antonio Togni

  DOI：10.1016/j.tetasy.2006.01.035

  日期：2006.2

  Monofluorination of beta-keto esters with Selectfluor (R) (1-chlorometliyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)) using CpTiCl3 as a catalyst, followed by amination with diazodicarboxylates using a Cu/Ph-Box catalyst leads to alpha-fluoro-alpha-hydrazino-beta-keto esters in good yields and good selectivities (ee up to 94%). (c) 2006 Elsevier Ltd. All rights reserved.
• 2-Aminopyrimidin-4(1H)-one as the novel bioisostere of urea: Discovery of novel and potent CXCR2 antagonists
  作者：Hongfu Lu、Ting Yang、Zhongmiao Xu、Paul B. Wren、Yueting Zhang、Xin Cai、Metul Patel、Kelly Dong、Qing Zhang、Wei Zhang、Xiaoming Guan、Jianing Xiang、John D. Elliott、Xichen Lin、Feng Ren

  DOI：10.1016/j.bmcl.2014.10.003

  日期：2014.12

  2-Aminopyrimidin-4(1H)-one was proposed as the novel bioisostere of urea. Bioisosteric replacement of the reported urea series of the CXCR2 antagonists with 2-aminopyrimidin-4(1H)-ones led to the discovery of the novel and potent CXCR2 antagonist 3e. 2-Aminopyrimidin-4(1H)-one derivative 3e demonstrated a good developability profile (reasonable solubility and high permeability) and superior chemical stability especially in simulated gastric fluid (SGF) compared with ureas. (C) 2014 Elsevier Ltd. All rights reserved.