1,1,1-trifluoro-4-methoxyoct-3-en-2-one | 1042447-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1-trifluoro-4-methoxyoct-3-en-2-one
• CAS: 1042447-58-4
• 化学式: C₉H₁₃F₃O₂
• 分子量: 210.196
• InChiKey: MLASLHPHLIBTSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  propyl(2-propynyl)amine 、 1,1,1-trifluoro-4-methoxyoct-3-en-2-one 以 乙腈 为溶剂， 反应 0.33h， 以93%的产率得到(E)-1,1,1-trifluoro-4-[propyl(prop-2-ynyl)amino]oct-3-en-2-one
  参考文献：
  名称：

  超声促进了N-炔丙基β-烯胺酮的合成。

  摘要：

  从β-烷氧基乙烯基三卤甲基[羧乙基]酮[R（3）C（O）CHC（R（1））OMe反应，其中R（3）= CF（3）的反应合成14种新型N-炔丙基β-烯胺），CCl（3），CO（2）Et和R（1）= Me，Et，Pr，Bu，i-Pent，CH（2）CH（2）CO（2）Me]与炔丙基胺[R（ 2）NHCH（2）CCH，其中报告了R（2）= Pr，PhCH（2）]。比较了通过微波辐射（MW），常规热加热（TH）和超声辐射（US）完成反应所需的产率，溶剂和反应时间。在US辐照下以良好至极好的收率（70-93％）获得了最佳结果。

  DOI：

  10.1016/j.ultsonch.2011.06.011

文献信息

• Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics
  作者：Marcos A. P. Martins、Paulo H. Beck、Lilian Buriol、Clarissa P. Frizzo、Dayse N. Moreira、Mara R. B. Marzari、Marcileia Zanatta、Pablo Machado、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1007/s00706-013-0930-x

  日期：2013.7

  (CX3C(O)CH=C(R1)OR, where X = F, Cl; R = Me, Et; R1 = H, Me, Et, n-Pr, i-Pr, n-Bu, i-Pent, Ph, 4-Cl-C6H4, 4-Br-C6H4, 4-F-C6H4) with pentafluorophenyl hydrazine. Pyrazoles were obtained under microwave irradiation in solvent-free conditions or under conventional heating in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM][BF4]. These procedures furnished products in moderate to good yields

  摘要1-（五氟苯基）-4,5-二氢-1 H-吡唑是根据4-烷氧基-1,1,1-三卤-3-烯丙基-2-酮的环缩合反应合成的（CX 3 C（O）CH = C（R 1）OR，其中X =氟，氯; R =甲基，乙基; R 1  = H，ME等，ñ -Pr，我-Pr，ñ -Bu，我-戊中，Ph，4- CL-C 6 H ^ 4，4 -溴-C 6 H ^ 4，4-FC 6 H ^ 4）与五氟苯基肼。吡唑是在无溶剂条件下于微波辐射下或在常规液体中于离子液体四氟硼酸1-丁基-3-甲基咪唑鎓[BMIM] [BF 4 ]中获得的。这些步骤在短的反应时间内以中等至良好的产率提供了产品。确定了在微波（MW）/无溶剂和常规热加热/ [BMIM] [BF 4 ]条件下进行的环缩合反应的原子经济性，反应质量效率（RME）和环境因子（E-factor）。RME和E因子表明，考虑到分离出的产物时，无溶剂程序的绿色始终低于[BMIM]
• Efficient preparation of novel N-propargylic β-enaminones from the reaction of β-alkoxyvinyltrihalomethyl[carboxy]ketones and propargylamines
  作者：Marcos A.P. Martins、Marcelo Rossatto、Liziê D. T. Prola、Dayse N. Moreira、Patrick T. Campos、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.3998/ark.5550190.0011.902

  日期：——

  Fifteen N-propargylic β-enaminones were synthesized from the reaction of propargyl amines [4X-PhNHCH2C≡CH, where X = H, Me] and 4-alkoxy-1,1,1-trihalo[ethoxy]-3-alken-2-ones [RC(O)CH=C(R)OMe, where R = CF3, CCl3, CO2Et and R = Me, Et, Pr, Bu, i-Pent, CH2CH2CO2Me]. The methodology described herein proceeded smoothly and furnished the products in good to high yields (70-95%).

  由炔丙胺[4X-PhNHCH2C≡CH，其中X = H，Me]和4-烷氧基-1,1,1-三卤代[乙氧基]-3-alken-2反应合成了15种N-炔丙基β-烯胺酮-ones [RC(O)CH=C(R)OMe，其中 R = CF3、CCl3、CO2Et 和 R = Me、Et、Pr、Bu、i-Pent、CH2CH2CO2Me]。本文描述的方法进行得很顺利，并以良好到高产率 (70-95%) 提供产品。
• Ionic liquid and Lewis acid combination in the synthesis of novel (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones
  作者：Dayse N. Moreira、Clarissa P. Frizzo、Kelvis Longhi、Aline B. Soares、Mara R. B. Marzari、Lilian Buriol、Sergio Brondani、Nilo Zanatta、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1007/s00706-011-0563-x

  日期：2011.12

  In this work, a new catalytic system to synthesize a series of new (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones from the cyclocondensation reaction of benzylidene cyanoacetohydrazide with 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)C(R-2) = C(R-1)(OR), where R = Me, Et; R-1 = H, Me, Pr, Bu, Ph, 4-Me-Ph, 4-F-Ph, 4-Cl-Ph, 4-Br-Ph; R-2 = H, Me and R-1,R-2 = -(CH2)(4)-] is presented. The products were obtained at room temperature in moderate to good yields (42-87%). Comparison of the catalytic system with a conventional method was not possible, because the products were obtained only when the new catalyst system-consisting of triethylamine and Lewis acid in ionic liquid [BMIM][BF4]-was used.
• Novel 4,5-bis(trifluoromethyl)-1H-pyrazoles through a concise sequential iodination-trifluoromethylation reaction
  作者：Andrizia F. Junges、Everton P. Pittaluga、Nilo Zanatta、Marcos A.P. Martins、Helio G. Bonacorso

  DOI：10.1016/j.tetlet.2019.04.031

  日期：2019.5

  An efficient protocol for the assembly of a new series of 1,3-disubstituted 4,5-bis(trifluoromethyl)-1H-pyrazoles - through a concise sequential iodination-trifluoromethylation reaction at the C-4 position of an initial series of 1-aryl-3-(alkyl/aryl)-5-trifluoromethyl-1H-pyrazoles (electronically deactivated heterocycles), using NIS and MFSDA, at good conversion yields and in short reaction times - is reported. (C) 2019 Elsevier Ltd. All rights reserved.
• Synergic Effects of Ionic Liquid and Microwave Irradiation in Promoting Trifluoromethylpyrazole Synthesis
  作者：Lilian Buriol、Clarissa P. Frizzo、Liziê D. T. Prola、Dayse N. Moreira、Mara R. B. Marzari、Elisandra Scapin、Nilo Zanatta、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1007/s10562-011-0571-9

  日期：2011.8

  The synthesis of 5-trifluoromethyl-1-phenyl-1H-pyrazoles from the reactions of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R-1)OR, where R = Me, Et; R-1 = H, Me, Bu, i-Bu, Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-IC6H4, fur-2-yl] with phenyl hydrazine in the presence of ionic liquid [BMIM][BF4] is reported. Synergic effects of ionic liquid and microwave irradiation in promoting pyrazole synthesis have been shown for the first time.