1,1,1-三氟-4-甲氧基-4-(萘-2-基)丁-3-烯-2-酮 | 1262322-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 1,1,1-三氟-4-甲氧基-4-(萘-2-基)丁-3-烯-2-酮
• 英文名称: 1,1,1-trifluoro-4-methoxy-4-(naphthalen-2-yl)but-3-en-2-one
• CAS: 1262322-08-6
• 化学式: C₁₅H₁₁F₃O₂
• 分子量: 280.246
• InChiKey: IBLVJJMBDLKDLG-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-4-甲氧基-4-(萘-2-基)丁-3-烯-2-酮 在 硫酸 作用下， 以 水 为溶剂， 反应 16.0h， 以74%的产率得到4,4,4-三氟-1-2-萘-1,3-丁烷二酮
  参考文献：
  名称：

  合成1-叔丁基-3(5)-三氟甲基-1H-吡唑的区域选择性和反应介质的比较研究

  摘要：

  介绍了从 4-烷氧基-1,1,1-三氟-3-烯烃-2 反应合成一系列 1-叔丁基-3(5)-(三氟甲基)-1H-吡唑的研究-ones [CF3C(O)CH=C(R1)(OR)，其中 R = Et 且 R1 = H 或 R = Me 且 R1 = Me、Ph、4-Me-C6H4、4-MeO-C6H4、4- F-C6H4、4-Cl-C6H4、4-Br-C6H4、4-I-C6H4、fur-2-yl、thien-2-yl或naphth-2-yl]与叔丁基肼盐酸盐。当[BMIM][BF4]（1-丁基-3-甲基咪唑四氟硼酸盐）和吡啶用作反应介质时，我们得到了1-叔丁基-3（5）-三氟甲基吡唑的混合物。当反应在乙醇中的 NaOH 中进行时，会形成具有高区域选择性的 5-三氟甲基-1-叔丁基-1H-吡唑。4-烷氧基-1,1水解后，生成1-叔丁基-3-三氟甲基-1H-吡唑，

  DOI：

  10.1002/ejoc.201201111

文献信息

• Trifluoromethyl-substituted 2,8-diaryl-imidazo[1,2-a][1,8]naphthyridines: Synthesis, remarkable optical emission, and redox and thermal properties
  作者：Steffany Z. Franceschini、Yuri G. Kappenberg、Fábio M. Luz、Jean C.B. Vieira、Marcos A.P. Martins、Nilo Zanatta、Clarissa P. Frizzo、Bernardo A. Iglesias、Helio G. Bonacorso

  DOI：10.1016/j.dyepig.2023.111514

  日期：2023.10

  of thirteen examples of 2,8-diaryl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridines (6) was synthesized at 21–96% yields, in which 2,8-diaryl = C6H5, 4-BrC6H4, 4-OMeC6H4, 4-CF3C6H4, and 2-naphtyl by intermolecular and regioselective [3+2] cyclocondensation reaction of a series of selected 7-aryl-2-amino-5-(trifluoromethyl)-[1,8]naphthyridines (3) with 1-aryl-2-bromo-ethanones (5). Aromatic amines

  一系列新颖的 2,8-二芳基-4-(三氟甲基)咪唑并[1,2- a ][1,8]萘啶 ( 6 ) 的十三个实例以 21–96% 的产率合成，其中 2,8-二芳基=C 6 H 5、4-BrC 6 H 4、4-OMeC 6 H 4、4-CF 3 C 6 H 4和2-萘基通过分子间和区域选择性的[3+2]环缩合反应一系列选定7-芳基-2-氨基-5-(三氟甲基)-[1,8]萘啶( 3 )与1-芳基-2-溴-乙酮( 5 )。芳香胺3和溴乙酮5通过先前报道的方法获得，该方法使2,6-二氨基-吡啶( 2 )与4-芳基-4-甲氧基-1,1,1-三氟丁-3-en-2-酮( 1 )反应得到3和一些苯乙酮4与元素溴合成5。所有新化合物6均由1 H-、13 C、19完全表征F NMR 和 IR 光谱、SC-XRD 和 HRMS 方法。通过 UV-Vis、稳态和时间分辨荧光发射（溶液和固态）、TD-DFT 计算和氧
• Ionic liquid/HCl catalyzed synthesis of 4-(trifluoromethyl)-2(1H)-pyrimidinones
  作者：Clarissa P. Frizzo、Mara R. B. Marzari、Caroline R. Bender、Izabelle M. Gindri、Jefferson Trindade、Lilian Buriol、Guilherme S. Caleffi、Helio G. Bonacorso、Nilo Zanata、Marcos A. P. Martins

  DOI：10.1007/s00706-013-1126-0

  日期：2014.5

  4-(Trifluoromethyl)-2(1H)-pyrimidinones were synthesized from the reaction between 1,1,1-trifluoro-4-methoxy-3-buten-2-ones [CF3C(O)C(R-2)C(R-1)(OCH3) where R-1 = Ph, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH3-C6H4, naphth-2-yl, 4-OCH3-C6H4, thien-2-yl and R-2 = H, CH3] and urea in the presence of ionic liquid [BMIM][BF4] combined with HCl. The results demonstrate that [BMIM][BF4]/HCl catalyzed the reaction in the absence of molecular solvents. Use of ionic liquid combined with HCl allowed the reaction temperatures to be increased to 100 A degrees C and decreased the reaction times from 48-72 to 3-6 h. The products were obtained in good yields (70-97 %).
• Resourceful synthesis of pyrazolo[1,5-a]pyrimidines under ultrasound irradiation
  作者：Lilian Buriol、Taiana S. München、Clarissa P. Frizzo、Mara R.B. Marzari、Nilo Zanatta、Helio G. Bonacorso、Marcos A.P. Martins

  DOI：10.1016/j.ultsonch.2013.02.006

  日期：2013.9

  Pyrazolo[1,5-a]pyrimidines were synthesized via the ultrasonic sonochemical method using the cyclo-condensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3(C)(O)CH = C(R)(OMe) - where R = Me, Bu, i-Bu, Ph, 4-Me-C6H4, 4-F-C6H4, 4-CI-C6H4, 4-Br-C6H4, naphth-2-yl and biphen-4-yl] - with 3-amino-5-methyl-1H-pyrazole in the presence of EtOH for 5 min. This methodology has several advantages, for example, it is a simple procedure, it has an easy work-up, Mild conditions, short reaction times (5 min) and produces satisfactory yields (61-98%). (C) 2013 Elsevier B.V. All rights reserved.
• An E-factor minimized solvent-free protocol for the preparation of 4,5-dihydro-5-(trifluoromethyl)-1H-pyrazoles
  作者：Lilian Buriol、Clarissa P. Frizzo、Dayse N. Moreira、Liziê D. T. Prola、Mara R. B. Marzari、Taiana S. München、Nilo Zantta、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1007/s00706-011-0464-z

  日期：2011.5

  The efficient synthesis of 4,5-dihydro-1H-pyrazoles from the reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R-1)(OR), where R = Me, Et and R-1 = H, Me, Et, Pr, i-Bu, Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, fur-2-yl, Naphth-2-yl, biphenyl-4-yl] and ethyl 3-hydrazino-3-oxopropionate [NH2NHC(O)CH2C(O)OEt] is reported. The products were obtained in good yields (72-87%). Two protocols were developed: (1) conventional thermal heating using EtOH as solvent and under solvent-free conditions, and (2) a microwave-assisted method using EtOH as solvent and under solvent-free conditions. The E-factor was determined for all protocols, and the results showed that the microwave-assisted method under solvent-free conditions results in a greener process.