β-ethyloxyvinyl bromodifluoromethyl ketone | 216431-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-ethyloxyvinyl bromodifluoromethyl ketone
• 英文别名: 1-bromo-4-ethoxy-1,1-difluorobut-3-en-2-one；β-ethyloxyvinyl bromodifluoromethyl enone
• CAS: 216431-81-1
• 化学式: C₆H₇BrF₂O₂
• 分子量: 229.021
• InChiKey: IJKFVLQFHXEEEK-UHFFFAOYSA-N

物化性质

• 沸点：
  157.6±40.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-ethyloxyvinyl bromodifluoromethyl ketone 在 吡啶 、 一氯化碘 作用下， 以 氯仿 为溶剂， 生成 (Z)-1-bromo-4-ethoxy-1,1-difluoro-3-iodobut-3-en-2-one
  参考文献：
  名称：

  Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones

  摘要：

  beta-Alkoxyvinyl bromodifluoromethyl ketones 1a, 1b and 1c were synthesized by the reaction of bromodifluoroacetic anhydride with appropriate vinyl ethers in high yields. The acyclic enone 1a reacted with amines to give the corresponding beta-aminovinyl bromodifluoromethyl ketones 2 in good yields. The reaction of la with electrophilic reagent ICI yielded alpha-iodoenone 4. The substitution reaction of the cyclic enones 1b and 1c with thio-nucleophiles gave the corresponding difluoromethylene thioethers 6. The three-component reactions of 2 with primary amines and formaldehyde gave multifunctional 1,2,3,4-tetrahydropyrimidine 3 in moderate yields. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.09.001
• 作为产物：
  描述：

  溴(二氟)乙酰氯 、 乙烯基乙醚 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到β-ethyloxyvinyl bromodifluoromethyl ketone
  参考文献：
  名称：

  Regioselective Synthesis of Rare 3-Halomethylphenols Based on Formal [3+3] Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes

  摘要：

  1,3-双(trimethylsilyloxy)-1,3-丁二烯与卤取代烯酮的环化反应，得到了3-二氟氯甲基、3-二氟溴甲基、3-二氯甲基和3-三氯甲基酚，具有很好的区域选择性。对二氯甲基的水解生成了功能化的3-甲酰基酚，这些化合物通过其他方法不容易获得。

  DOI：

  10.1055/s-2008-1077877

文献信息

• Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov
  作者：Karen V. Tarasenko、Igor I. Gerus、Valery P. Kukhar、Vitaly V. Polovinko

  DOI：10.1135/cccc2008095

  日期：——

  New bromodifluoromethyl enaminones 1a–1f and γ-bromo-β-morpholinopropenyl fluoromethyl ketones 2a, 2b were synthesized. N-Substituted bromodifluoromethyl enaminones 1a–1d do not react with triethyl or diethyl phosphites, whereas N-acylated enaminones 1e, 1f gave difluorodienyl phosphates 4a, 4b as Perkow rearrangement products. Fluoroketone 2a reacts easily with triethyl phosphite according to the Arbuzov protocol and a perspective building block – trifluoromethyl-containing phosphonate 7a is formed.

  合成了新的溴二氟甲基烯酮1a-1f和γ-溴-β-吗啡基丙烯基氟甲基酮2a、2b。N-取代的溴二氟甲基烯酮1a-1d不与三乙基或二乙基膦酸酯反应，而N-酰基化的烯酮1e、1f则形成了二氟二烯基磷酸酯4a、4b作为Perkow重排产物。氟酮2a根据Arbuzov协议容易与三乙基膦酸酯反应，形成了一个前景建筑模块-三氟甲基含磷酸酯7a。
• Regioselective Synthesis of Rare 3-Halomethylphenols Based on Formal [3+3] Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes
  作者：Peter Langer、Mathias Lubbe、Constantin Mamat

  DOI：10.1055/s-2008-1077877

  日期：——

  The cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with halo-substituted enones afforded 3-difluorochloromethyl-, 3-difluorobromomethyl-, 3-dichloromethyl-, and 3-trichloro-methylphenols with very good regioselectivity. The hydrolysis of the dichloromethyl group gave functionalized 3-formylphenols, which are not readily available by other methods.

  1,3-双(trimethylsilyloxy)-1,3-丁二烯与卤取代烯酮的环化反应，得到了3-二氟氯甲基、3-二氟溴甲基、3-二氯甲基和3-三氯甲基酚，具有很好的区域选择性。对二氯甲基的水解生成了功能化的3-甲酰基酚，这些化合物通过其他方法不容易获得。
• Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones
  作者：Xiang Fang、Yang Chen、Daming He、Xianjin Yang、Fanhong Wu

  DOI：10.1016/j.jfluchem.2008.09.001

  日期：2008.12

  beta-Alkoxyvinyl bromodifluoromethyl ketones 1a, 1b and 1c were synthesized by the reaction of bromodifluoroacetic anhydride with appropriate vinyl ethers in high yields. The acyclic enone 1a reacted with amines to give the corresponding beta-aminovinyl bromodifluoromethyl ketones 2 in good yields. The reaction of la with electrophilic reagent ICI yielded alpha-iodoenone 4. The substitution reaction of the cyclic enones 1b and 1c with thio-nucleophiles gave the corresponding difluoromethylene thioethers 6. The three-component reactions of 2 with primary amines and formaldehyde gave multifunctional 1,2,3,4-tetrahydropyrimidine 3 in moderate yields. (c) 2008 Elsevier B.V. All rights reserved.