3,4-bis(trifluoromethyl)-2-furancarboxylic acid | 134429-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3,4-bis(trifluoromethyl)-2-furancarboxylic acid
• 英文别名: 3,4-bis(trifluoromethyl)furan-2-oic acid；3,4-Bis(trifluoromethyl)-2-furoic acid；3,4-Bis(trifluoromethyl)furan-2-carboxylic acid
• CAS: 134429-08-6
• 化学式: C₇H₂F₆O₃
• 分子量: 248.081
• InChiKey: NFBNUAWOZGYFLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙醇 、 3,4-bis(trifluoromethyl)-2-furancarboxylic acid 在 三甲基氯硅烷 作用下， 生成 ethyl 3,4-bis(trifluoromethyl)furan-2-oate
  参考文献：
  名称：

  Reaction of 2-lithio-3.4-bis(trifluoromethyl)furan with electrophiles

  摘要：

  2-Substituted-3,4-bis(trifluoromethyl)furans activated CH = C(CF3)C(CF3) = CR-O [R = CO2H (and hence R = CO2Me and CO2Et), CHO, CHPhOH, CHMeOH, CH(OH)CH = CH2] are obtained in good yield by treatment of the corresponding 2-lithiofuran with the appropriate electrophile. With methyl acrylate, initial attack occurs at carbonyl carbon but the resulting ketone (R = COCH = CH2) undergoes Michael addition with an excess of the lithium salt. From the reaction with dichloromaleic anhydride, 5,5-bis[3,4-bis(trifluoromethyl)-2-furyl]-3,4-dichloro-2-furanone is formed in 85% yield.

  DOI：

  10.1016/s0022-1139(00)80121-9
• 作为产物：
  描述：

  2-呋喃甲基乙酯 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 3,4-bis(trifluoromethyl)-2-furancarboxylic acid
  参考文献：
  名称：

  Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and 1,1,1,2,4,4,4-heptafluorobut-2-ene

  摘要：

  通过六氟丁-2-炔加成形成的环加成物，可以转化为双(三氟甲基)苯、苯酚和呋喃衍生物。四(三氟甲基)苯也可以合成。七氟丁-2-烯2对于与环戊二烯和呋喃的反应也非常有效。在升高的温度下，2与呋喃衍生物反应可以非常有效地实现3,4-双(三氟甲基)呋喃衍生物的“一锅”合成。

  DOI：

  10.1039/p19960001095

文献信息

• Nishida, Masakazu; Hayakawa, Yoshio; Matsui, Masaki, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 2, p. 225 - 229
  作者：Nishida, Masakazu、Hayakawa, Yoshio、Matsui, Masaki、Shibata, Katsuyoshi、Muramatsu, Hiroshige

  DOI：——

  日期：——
• NISHIDA, MASAKAZU;HAYAKAWA, YOSHIO;MATSUI, MASAKI;SHIDATA, KATSUYOSHI;MUR+, J. HETEROCYCL. CHEM., 28,(1991) N, C. 225-229
  作者：NISHIDA, MASAKAZU、HAYAKAWA, YOSHIO、MATSUI, MASAKI、SHIDATA, KATSUYOSHI、MUR+

  DOI：——

  日期：——
• Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and 1,1,1,2,4,4,4-heptafluorobut-2-ene
  作者：Richard D. Chambers、Alex J. Roche、Michael H. Rock

  DOI：10.1039/p19960001095

  日期：——

  Cycloadducts, formed by addition of hexafluorobut-2-yne, may be transformed into bis(trifluoromethyl)-benzene, -phenol and -furan derivatives. Tetrakis(trifluoromethyl)benzene may also be produced. Heptafluorobut-2-ene 2 is also a very efficient dienophile for reactions with cyclopentadiene and furan. Reaction of 2 with furan derivatives at elevated temperatures gives a very effective ‘one pot’ synthesis of 3,4-bis(trifluoromethyl)furan derivatives.

  通过六氟丁-2-炔加成形成的环加成物，可以转化为双(三氟甲基)苯、苯酚和呋喃衍生物。四(三氟甲基)苯也可以合成。七氟丁-2-烯2对于与环戊二烯和呋喃的反应也非常有效。在升高的温度下，2与呋喃衍生物反应可以非常有效地实现3,4-双(三氟甲基)呋喃衍生物的“一锅”合成。
• Reaction of 2-lithio-3.4-bis(trifluoromethyl)furan with electrophiles
  作者：Aliyu B. Abubakar、Brian L. Booth、Anthony E. Tipping

  DOI：10.1016/s0022-1139(00)80121-9

  日期：1991.12

  2-Substituted-3,4-bis(trifluoromethyl)furans activated CH = C(CF3)C(CF3) = CR-O [R = CO2H (and hence R = CO2Me and CO2Et), CHO, CHPhOH, CHMeOH, CH(OH)CH = CH2] are obtained in good yield by treatment of the corresponding 2-lithiofuran with the appropriate electrophile. With methyl acrylate, initial attack occurs at carbonyl carbon but the resulting ketone (R = COCH = CH2) undergoes Michael addition with an excess of the lithium salt. From the reaction with dichloromaleic anhydride, 5,5-bis[3,4-bis(trifluoromethyl)-2-furyl]-3,4-dichloro-2-furanone is formed in 85% yield.