1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diol | 202074-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diol
• 英文别名: 4-(Benzenesulfonyl)-1,1,1-trifluorobut-3-ene-2,2-diol；4-(benzenesulfonyl)-1,1,1-trifluorobut-3-ene-2,2-diol
• CAS: 202074-35-9
• 化学式: C₁₀H₉F₃O₄S
• 分子量: 282.24
• InChiKey: BGEZDULKRPRIDI-UHFFFAOYSA-N

物化性质

• 沸点：
  502.1±50.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diol 在 苯硫酚 作用下， 以 乙腈 为溶剂， 以90%的产率得到phenyl β-(trifluoroacetyl)vinyl sulfide
  参考文献：
  名称：

  摘要：

  Oxidation of beta-(trifluoroacetyl)vinyl sulfides afforded a series of the corresponding sulfones. The reactions of sulfones with various alkyl- and arylthiols were studied. These reactions provide the basis for a new procedure for the synthesis of beta-(trifluoroacetyl)vinyl sulfides.

  DOI：

  10.1023/a:1021620228529
• 作为产物：
  描述：

  phenyl β-(trifluoroacetyl)vinyl sulfone 在 水 作用下， 以100%的产率得到1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diol
  参考文献：
  名称：

  摘要：

  Oxidation of beta-(trifluoroacetyl)vinyl sulfides afforded a series of the corresponding sulfones. The reactions of sulfones with various alkyl- and arylthiols were studied. These reactions provide the basis for a new procedure for the synthesis of beta-(trifluoroacetyl)vinyl sulfides.

  DOI：

  10.1023/a:1021620228529

文献信息

• A Facile Access to 2-CF₃-Imidazo[1,2-<i>a</i>]pyridines<i />
  作者：Valentine G. Nenajdenko、Arcady L. Krasovsky、Elizabeth S. Balenkova

  DOI：10.1055/s-2002-33106

  日期：——

  A new simple and efficient way to 2-CF3-imidazo[1,2-a]pyridines and 2-CF3-imidazo[1,2-a]quinolines by the reaction of 1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diols 1a,b with various 2-aminopyridines is described. The cyclization reaction proceeds diastereospecifically under mild conditions in water.

  通过1,1,1-三氟-4-(苯磺酰基)丁-3-烯-2,2-二醇1a,b与各种2-氨基吡啶的反应,描述了一种合成2-CF3-咪唑并[1,2-a]吡啶和2-CF3-咪唑并[1,2-a]喹啉的新型简单高效方法。该环化反应在温和的水溶液条件下可以立体专一性地进行。
• A Novel Efficient Synthesis of Heteroaryl Substituted α,β-Unsaturated Trifluoromethyl Ketones
  作者：Valentine Nenajdenko、Arkady Krasovsky、Mikhail Lebedev、Elizabeth Balenkova

  DOI：10.1055/s-1997-1038

  日期：——

  A synthesis of a novel electrophilic reagent 1,1,1-trifluoro-4-(phenylsulfonyl)-but-3-ene-2,2-diol 2 is described. The reaction of 2 with various electron-rich heteroaromatics such as furans, pyrroles, indoles is investigated. The addition-elimination reaction proceeds under mild conditions stereospecifically and permits a novel one-step procedure for the preparation of trifluoroacetylvinyl substituted heterocycles in high yield. In all cases only E-isomers of unsaturated CF3 ketones were obtained.

  本文介绍了一种新型亲电试剂 1,1,1-三氟-4-(苯磺酰基)-丁-3-烯-2,2-二醇 2 的合成。研究了 2 与各种富电子杂芳烃（如呋喃、吡咯、吲哚）的反应。加成-消除反应在温和的条件下立体定向地进行，并允许采用一种新颖的一步法高产率制备三氟乙酰乙烯基取代的杂环。在所有情况下，只得到了不饱和 CF3 酮的 E 异构体。
• Efficient Syntheses of New CF₃-containing Diazolopyrimidines
  作者：Valentine Nenajdenko、Arcady Krasovsky、Anton Hartulyari、Elizabeth Balenkova

  DOI：10.1055/s-2002-19313

  日期：——

  A new simple and efficient way to CF3-containing pyrimido[1,2-a]benzimidazole and pyrazolo[1,5-a]pyrimidines, by the reaction of 1,1,1-trifluoro-4-sulfonyl-but-3-ene-2,2-dioles 1a,b with aminoheterocycles is described. The influence of reaction conditions and nature of the aminoheterocycles on regiochemistry was investigated.

  本文描述了一种新的简单有效的方法，通过1,1,1-三氟-4-磺酰基-3-丁烯-2,2-二醇1a,b与氨基杂环的反应，制备含CF3的嘧啶并[1,2-a]苯并咪唑和吡唑并[1,5-a]嘧啶。研究了反应条件和氨基杂环性质对反应化学的影响。
• Diels–Alder reactions of β-trifluoroacetylvinylsulfones
  作者：Arkady L Krasovsky、Valentine G Nenajdenko、Elizabeth S Balenkova

  DOI：10.1016/s0040-4020(00)00980-7

  日期：2001.1

  Diels–Alder reactions of β-trifluoroacetylvinylsulfones with 1,3-dienes in CH2Cl2 afforded corresponding mono- and polycycloadducts. A possibility of stereo- and regioselective cycloaddition was investigated. Elimination of sulfonyl group from cycloadducts leads to α,β-unsaturated trifluoromethylketones in good yields.

  β-三氟乙酰基乙烯基砜与1,3-二烯在CH 2 Cl 2中的Diels-Alder反应得到相应的单环和多环加合物。研究了立体和区域选择性环加成的可能性。从环加合物中消除磺酰基可产生高产率的α，β-不饱和三氟甲基酮。
• Synthesis of New Fluorine Containing Triazolo- and Tetrazolopyrimidines
  作者：Arcady L. Krasovsky、Andrew M. Moiseev、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1055/s-2002-28512

  日期：——

  reaction of 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b with corresponding aminoazoles was investigated. A new simple and efficient way for the regioselective synthesis of 5-CF 3 or 7-CF 3 triazolo- and tetrazolopyrimidines is described.

  研究了 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b 与相应的氨基唑的反应。描述了一种新的简单有效的区域选择性合成 5-CF 3 或 7-CF 3 三唑并四唑嘧啶的方法。