2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-6-phenyl-2,4-cyclohexadienone | 152342-45-5

• 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: 2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-6-phenyl-2,4-cyclohexadienone
• 英文别名: 6-phenyl-3-pentafluorophenoxy-2,4,5,6-tetrafluoro-2,4-cyclohexadienone；3-(pentafluorophenoxy)tetrafluoro-6-phenylcyclohexa-2,4-dienone；2,4,5,6-Tetrafluoro-3-(pentafluorophenoxy)-6-phenylcyclohexa-2,4-dien-1-one；2,4,5,6-tetrafluoro-3-(2,3,4,5,6-pentafluorophenoxy)-6-phenylcyclohexa-2,4-dien-1-one
• CAS: 152342-45-5
• 化学式: C₁₈H₅F₉O₂
• 分子量: 424.222
• InChiKey: VMDOAGVHQZDDSM-UHFFFAOYSA-N

物化性质

• 沸点：
  307.8±42.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-6-phenyl-2,4-cyclohexadienone 以 正己烷 为溶剂， 反应 48.0h， 以63%的产率得到3-pentafluorophenoxy-1,2,4-trifluorodibenzofuran
  参考文献：
  名称：

  Photochemical cyclization of polyfluorinated aryloxo-1,2-dihydronaphthalenes and 6-phenyl-3-phenoxy-2,4-cyclohexadienone

  摘要：

  On irradiation of solutions of polyfluorinated aryloxo-1,2-dihydronaphthalenes and 6-phenyl-3-phenoxy-2,4-cyclohexadienone, the main reaction pathway is cyclization leading to polyfluorinated benzonaphtho- and dibenzo-furans.

  DOI：

  10.1016/0022-1139(93)02947-d
• 作为产物：
  描述：

  phenyllead(IV) triacetate 、 五氟苯酚酸钠 以 四氯化碳 为溶剂， 生成 2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-6-phenyl-2,4-cyclohexadienone
  参考文献：
  名称：

  A new method of organophosphorus (III) compounds oxidative fluorination by fluorinated alkylazides

  摘要：

  DOI：

  10.1016/s0022-1139(00)83821-x

文献信息

• Reactions of polyfluorinated cyclohexadienones with diazoalkanes. Part 1. Formation of cyclopropanes from polyfluorinated cyclohexa-2,4-dienones with diazomethane and phenyldiazomethane
  作者：Vladimir N. Kovtonyuk、Ljubov S. Kobrina、Yurij V. Gatilov、Irina Yu. Bagryanskaya、Roland Fröhlich、Günter Haufe

  DOI：10.1039/b001618g

  日期：——

  The reaction of 6-chloro-2,3,4,5,6-pentafluorocyclohexa-2,4-dienone (1) with diazomethane gives a mixture of two diastereoisomers of 6-chloro-3a,4,5,6,7a-pentafluoro-3,3a,6,7a-tetrahydrospiro[indazole-7,2′-oxirane] 2a and 2b. In contrast phenyldiazomethane reacts with polyfluorinated cyclohexa-2,4-dienones 1, 9, and 10 in acetonitrile to form the fluorinated 7-phenylbicyclo[4.1.0]hept-4-en-2-ones 4a

  的反应 6-氯-2,3,4,5,6-五氟环己-2,4-二烯酮（1）与重氮甲烷得到6-氯-3a，4、5、6、7a-五氟-3,3a，6,7a-四氢螺[吲唑-7,2'-环氧乙烷] 2a和2b的两种非对映异构体的混合物。相比之下苯基重氮甲烷与多氟化环己-2,4-二烯酮进行反应1，9和10中乙腈形成氟化的7-苯基双环[4.1.0]庚-4-烯-2-酮4a，b，11a，b和12a，b作为主要产物。该反应显示出对电极极性的显着依赖性。溶剂。虽然形成了复杂的产品混合物戊烷，反应在 乙腈继续以高立体选择性进行，仅给出两种内聚异构体。
• Diels–Alder reactions of polyfluorinated 2,4-cyclohexadienones with α- and β-fluorostyrenes
  作者：A.A. Bogachev、L.S. Kobrina、O.G.J. Meyer、G. Haufe

  DOI：10.1016/s0022-1139(99)00040-8

  日期：1999.7

  proceed as [4+2]-cycloadditions with inverse electron demand. In contrast, a polyfluorinated 2,4-cyclohexadienone with a methoxy group in the three-position shows no reaction with either α- or β-fluorostyrene, but does undergo rearrangement to give a polyfluorinated 2,5-cyclohexadienone. 4-Fluorooct-4-en-3-one is inert to all polyfluorinated 2,4-cyclohexadienones.

  在碳3上带有一个额外的吸电子基团的多氟2,4-环己二酮与α-和β-氟代苯乙烯的热反应产生非对映Diels–Alder产物的混合物。假定过程是协调一致的，这些反应将以[4 + 2]-环加成进行，且电子反需求。相反，在三位具有甲氧基的多氟2,4-环己二酮与α-或β-氟苯乙烯均不发生反应，但会发生重排而得到多氟2,5-环己二酮。4-氟八-4-烯-3-酮对所有多氟2,4-环己二酮均呈惰性。
• ——
  作者：V. N. Kovtonyuk、L. S. Kobrina

  DOI：10.1023/a:1015597112943

  日期：——
• Bogachev; Bagryanskaya; Rybalova, Russian Journal of General Chemistry, 1996, vol. 66, # 8, p. 1284 - 1293
  作者：Bogachev、Bagryanskaya、Rybalova、Gatilov、Kobrina

  DOI：——

  日期：——
• Novel phosphabicyclo[2.2.2]-octa-2,5-dienes from iPr2N-C  P or tBu-C  P and a polyfluorinated cyclohexadienone
  作者：Joseph Grobe、Duc Le Van、Burkhardt Broschk、Lioubov S. Kobrina

  DOI：10.1016/s0040-4039(00)60639-1

  日期：1993.9

  The reaction of the phosphaalkyne iPr2N-C=P (1) with 6-phenyl-3-pentafluorophenoxy-tetrafluorocyclohexa2,4-dien-1-one (2) affords the novel [4+2] cycloadduct 3 in quantitative yield. The same reaction carried out with t-butylphosphaethyne (4) only takes place at 60-degrees-C giving a mixture of isomers of the Diels-Alder compounds 5a to 5c in the ratio 90:4:6. 5a can be isolated in pure form but - dissolved in chloroform - at 20-degrees-C unexpectedly converts into the 1-phospha-tetracyclo[4.2.0.0.2.8.05,7]octane 6 via an intramolecular [2+2] cycloaddition reaction.