1t-ethoxy-5,5,5-trifluoro-4-trifluoromethyl-pent-1-en-3-one | 25631-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1t-ethoxy-5,5,5-trifluoro-4-trifluoromethyl-pent-1-en-3-one
• 英文别名: (E)-1-ethoxy-5,5,5-trifluoro-4-(trifluoromethyl)pent-1-en-3-one
• CAS: 25631-66-7
• 化学式: C₈H₈F₆O₂
• mdl: MFCD28133003
• 分子量: 250.141
• InChiKey: KGQZOWDBTNLUIK-ONEGZZNKSA-N

物化性质

• 沸点：
  92-93 °C(Press: 19 Torr)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3,3-三氟-2-(三氟甲基)丙-1-烯-1-酮 、 1t-ethoxy-5,5,5-trifluoro-4-trifluoromethyl-pent-1-en-3-one 生成 3,3,3-Trifluoro-2-trifluoromethyl-propionic acid 1-((E)-2-ethoxy-vinyl)-3,3,3-trifluoro-2-trifluoromethyl-propenyl ester
  参考文献：
  名称：

  Fluoroketenes. V. Cycloadditions to the bis(trifluoromethyl)ketene carbonyl group

  摘要：

  DOI：

  10.1021/jo00835a029
• 作为产物：
  描述：

  3,3,3-trifluoro-2-trifluoromethylpropionyl chloride 、 乙烯基乙醚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以56%的产率得到1t-ethoxy-5,5,5-trifluoro-4-trifluoromethyl-pent-1-en-3-one
  参考文献：
  名称：

  Synthesis and Properties of β-Ethoxyvinyl Polyfluoroalkyl Ketones

  摘要：

  通过含有不同组成和结构的聚氟烷基酸氯与乙烯基乙醚的酰基化反应，合成了一系列β-乙氧基乙烯基聚氟烷基酮。进行了这些标题化合物与胺类的一些典型亲核反应。通过β-乙氧基乙烯基聚氟烷基酮与脲的反应，合成了两种新的含氟嘧啶烷醇。

  DOI：

  10.1055/s-2000-6386

文献信息

• Halogenation of β-Alkoxyvinyl Polyhaloalkyl Ketones: A Convenient Route for the Synthesis of α-Chloro- or α-Bromo-β-alkoxyvinyl Polyhaloalkyl Ketones
  作者：Igor I. Gerus、Liliya M. Kacharova、Sergei I. Vdovenko

  DOI：10.1055/s-2001-11435

  日期：——

  A number of α-chloro- and α-bromo-β-alkoxyvinyl polyhaloalkyl ketones 4 and 5 were synthesized in high yields by halogenation of β-alkoxyvinyl polyhaloalkyl ketones 1 with chlorine or bromine and further dehydrohalogenation of dihalo-intermediates 2 and 3 with pyridine. The Z configuration of ketones 4 and 5 was deduced from X-ray analysis and NMR spectra. Some typical nucleophilic reactions of the title compounds 4 and 5 with amines were carried out to check their reactivity.

  通过氯或溴对δ-烷氧基乙烯基多卤烷基酮 1 进行卤化，并进一步用吡啶对二氢中间体 2 和 3 进行脱氢卤化，高产率地合成了一些δ-氯和δ-溴烷氧基乙烯基多卤烷基酮 4 和 5。根据 X 射线分析和核磁共振光谱推断出了酮 4 和酮 5 的 Z 构型。标题化合物 4 和 5 与胺进行了一些典型的亲核反应，以检验它们的反应活性。
• β-Ethoxyvinyl polyfluoroalkyl ketones — versatile synthones in fluoroorganic chemistry
  作者：I.I. Gerus、M.G. Gorbunova、V.P. Kukhar

  DOI：10.1016/0022-1139(94)03130-4

  日期：1994.12

  material for the synthesis of various fluoro-containing compounds such as heterocycles, enones, enaminones and chelate complexes. The 4,4,4-trifluoro-3-oxo-l-butenyl group formed by β-ethoxyvinyl trifluoromethyl ketone is a suitable protecting group for the N-H terminal of amino acids in peptide synthesis. The formation of peptides using these protected amino acids occurs without racemization.

  我们已经发现，容易获得的β-乙氧基乙烯基三氟甲基酮是合成各种含氟化合物（例如杂环，烯酮，烯胺酮和螯合物）的方便和全面的起始原料。由β-乙氧基乙烯基三氟甲基酮形成的4,4,4-三氟-3-氧-1-丁烯基是肽合成中氨基酸NH末端的合适保护基。使用这些受保护的氨基酸形成肽时不会发生外消旋作用。
• Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones
  作者：Igor S. Kruchok、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/s0040-4020(00)00603-7

  日期：2000.8

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in beta-position of alpha,beta-enone is the important condition for realization of 1,4-addition. Ambient temperature (25 degrees C) or base catalyst (NEt3) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I-2) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated fluorine-containing ketones containing CN- and ethoxy groups at the beta-position. (C) 2000 Published by Elsevier Science Ltd.
• Synthesis and Properties of β-Ethoxyvinyl Polyfluoroalkyl Ketones
  作者：Marine G. Gorbunova、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1055/s-2000-6386

  日期：——

  A number of β-ethoxyvinyl polyfluoroalkyl ketones were synthesized by acylation of ethyl vinyl ether with acid chlorides containing polyfluoroalkyl groups of different composition and structure. Some typical nucleophilic reactions of the title compounds with amines were carried out. Two new fluoro-containing pyrimidinoles were synthesized by the reaction of β-ethoxyvinyl polyfluoroalkyl ketones with urea.

  通过含有不同组成和结构的聚氟烷基酸氯与乙烯基乙醚的酰基化反应，合成了一系列β-乙氧基乙烯基聚氟烷基酮。进行了这些标题化合物与胺类的一些典型亲核反应。通过β-乙氧基乙烯基聚氟烷基酮与脲的反应，合成了两种新的含氟嘧啶烷醇。
• Fluoroketenes. V. Cycloadditions to the bis(trifluoromethyl)ketene carbonyl group
  作者：David C. England、Carl G. Krespan

  DOI：10.1021/jo00835a029

  日期：1970.10