(Z)-3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one | 341527-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one
• 英文别名: 3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-2-one；(Z)-3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-2-one
• CAS: 341527-27-3
• 化学式: C₆H₆BrF₃O₂
• 分子量: 247.012
• InChiKey: ONAMOZNIUGKDIK-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one 在 叔丁基锂 、 sodium amide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 生成 (E)-1-ethoxy-3-trifluoromethyl-1,3-butadiene
  参考文献：
  名称：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and Congeners as Diels−Alder Components Opening an Entry to Functionalized (Trifluoromethyl)benzenes and -pyridines

  摘要：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifIuoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with dimethyl acetylenedicarboxylate and methyl propiolate to provide trifluoromethyl-substituted phthalates (2, 6 and 10) or benzoates (3, 7, 8 and 11). Satisfactory yields [of 4-(trifluoromethyl)pyridinecarboxylic acids 4 and 12] can even be achieved with methyl cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200205)2002:9<1490::aid-ejoc1490>3.0.co;2-1
• 作为产物：
  描述：

  1-乙氧基-3-三氟甲基-1,3-丁二烯 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(Z)-3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one
  参考文献：
  名称：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and Congeners as Diels−Alder Components Opening an Entry to Functionalized (Trifluoromethyl)benzenes and -pyridines

  摘要：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifIuoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with dimethyl acetylenedicarboxylate and methyl propiolate to provide trifluoromethyl-substituted phthalates (2, 6 and 10) or benzoates (3, 7, 8 and 11). Satisfactory yields [of 4-(trifluoromethyl)pyridinecarboxylic acids 4 and 12] can even be achieved with methyl cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200205)2002:9<1490::aid-ejoc1490>3.0.co;2-1

文献信息

• A new synthetic route to 3-polyfluoroalkyl-containing pyrroles
  作者：Elena N. Shaitanova、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/j.tetlet.2007.12.048

  日期：2008.2

  A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1,2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.

  据报导一种基于逐步反应的3-多氟烷基吡咯的新颖方法：将Me 3 SiCN 1，2-加成至β-烷氧基乙烯基多氟烷基酮，用LiAlH 4还原并随后通过分子内环化进行水解。在吡咯环的3位上的各种多氟烷基的水解不稳定性是明显的，并提出了水解的途径。
• 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。
• Reaction of α-halogen substituted β-ethoxyvinyl trifluoromethyl ketones with 2-aminopyridine: new route to trifluoroacetyl-containing heterocycles
  作者：Liliya M Kacharova、Igor I Gerus、Alexey D Kacharov

  DOI：10.1016/s0022-1139(02)00190-2

  日期：2002.10

  The reaction of α-halosubstituted β-ethoxyvinyl trifluoromethyl ketones with 2-aminopyridine gives 3-trifluoroacetyl imidazo[1,2-a]pyridine and 3-halo-1,1,1-trifluoro-4-(2-pyridinylamino)-3-buten-2-ones. The product ratio depends on the nature of the α-halogen atom and the solvent.

  α-卤代β-乙氧基乙烯基三氟甲基酮与2-氨基吡啶的反应得到3-三氟乙酰基咪唑并[1,2- a ]吡啶和3-卤代-1,1,1-三氟-4-（2-吡啶基氨基）-3 -丁2个。产物比率取决于α-卤素原子和溶剂的性质。
• Regioselective synthesis of 1-aryl-4-bromo-5-trifluoromethylpyrazoles
  作者：V. G. Nenajdenko、A. L. Reznichenko、E. S. Balenkova

  DOI：10.1007/s11172-006-0233-z

  日期：2006.1

  A novel regioselective route to 1-aryl-4-bromo-5-trifluoromethylpyrazoles involves reactions of arylhydrazines with 3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-2-one.

  一种新颖的1-芳基-4-溴-5-三氟甲基吡唑的位点选择性合成路线涉及芳基肼与3-溴-4-乙氧基-1,1,1-三氟丁-3-烯-2-酮的反应。
• .beta.-fluoroacyl-.beta.-halovinyl alkyl ethers
  申请人：Bayer Aktiengesellschaft

  公开号：US04876393A1

  公开（公告）日：1989-10-24

  Novel .beta.-fluoroacyl-.beta.-halogenovinyl alkyl ethers of the formula ##STR1## in which R.sup.1 is a fluorinated alkyl group having 1 to 9 carbon atoms, Hal is a halogen atom, and R.sup.2 is an alkyl group having 1 to 7 carbon atoms, useful as insecticide intermediates, are produced by reacting a .beta.-fluoroacylvinyl ether of the formula R.sup.1 --CO--CH.dbd.CH--OR.sup.2 (II) with a halogenating agent at a temperature of -70.degree. C. to +80.degree. C., to produce a halogenation product of the formula ##STR2## and dehydrohalogenating (III) at a temperature of -20.degree. C. to +100.degree. C.

  公式为##STR1##的新型.beta.-氟酰基-.beta.-卤代乙烯基烷基醚，其中R.sup.1是具有1到9个碳原子的氟化烷基，Hal是卤素原子，R.sup.2是具有1到7个碳原子的烷基，可用作杀虫剂中间体。通过在温度为-70°C至+80°C下，将公式R.sup.1-CO-CH.dbd.CH-OR.sup.2(II)的.beta.-氟酰基乙烯醚与卤化剂反应，以产生公式##STR2##的卤化产物，然后在温度为-20°C至+100°C下进行脱卤反应(III)。