2,2,2-三氟-1-(2-甲氧基-1-环己烯-1-基)乙酮 | 158432-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2,2-三氟-1-(2-甲氧基-1-环己烯-1-基)乙酮
• 英文名称: 2-trifluoroacetyl-1-methoxycyclohexene
• 英文别名: 2,2,2-Trifluoro-1-(2-methoxycyclohex-1-en-1-yl)ethan-1-one；2,2,2-trifluoro-1-(2-methoxycyclohexen-1-yl)ethanone
• CAS: 158432-45-2
• 化学式: C₉H₁₁F₃O₂
• 分子量: 208.18
• InChiKey: DQDMBFWSWBXMGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-1-(2-甲氧基-1-环己烯-1-基)乙酮 在 盐酸 、 硫酸 、 盐酸羟胺 作用下， 反应 13.0h， 生成 3-Trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]isoxazole
  参考文献：
  名称：

  Martins, Marcos A. P.; Flores, Alex F. C.; Freitag, Rogerio, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 731 - 734

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 2,2,2-三氟-1-(2-甲氧基-1-环己烯-1-基)乙酮
  参考文献：
  名称：

  Eco-friendly synthesis and antioxidant activity of new trifluoromethyl-substituted N -(pyrimidin-2-yl)benzo[ d ]thiazol-2-amines and some N-derivatives

  摘要：

  AbstractA convenient and environmentally benign procedure for the synthesis of a new series of trifluoromethyl-substituted N-(pyrimidin-2-yl)benzo[d]thiazol-2-amines by the cyclocondensation reaction of (benzo[d]thiazolyl)guanidine with either 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones or 2,2,2-trifluoro-1-(2-methoxycyclohexen-1-en-1-yl)ethanone is described. The main reactions

  DOI：

  10.1007/s00706-016-1829-0

文献信息

• New one-pot, efficient, and regioselective method for the synthesis of 3-Trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs
  作者：Helio G. Bonacorso、Michele S. Correa、Liliane M.F. Porte、Everton P. Pittaluga、Nilo Zanatta、Marcos A.P. Martins

  DOI：10.1016/j.tetlet.2012.07.119

  日期：2012.10

  An efficient and regioselective procedure for the synthesis of a series of alkyl(aryl/heteroaryl) substituted 3-trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs, from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones [CX3C(O)CR2=CR1(OMe/OEt), where R1 = H, Me, Ph, 2-Furyl; R2 = H; R1-R2 = -C4H8- and X = F, Cl] and 1-phenylsemicarbazide in an acidified alcoholic

  从4-烷氧基-1,1,1的环缩合反应合成一系列烷基（芳基/杂芳基）取代的3-三氟甲基-1 H -1-苯基吡唑和3-羧酸烷基酯类似物的有效和区域选择性程序-trihaloalk-3-en-2-ones [CX 3 C（O）CR 2 = CR 1（OMe / OEt），其中R 1 = H，Me，Ph，2-呋喃基；R 2＝ H；在酸性醇介质（R 3 OH / H 2 SO 4）中，R 1 -R 2 = -C 4 H 8-和X = F，Cl]和1-苯基氨基脲，其中R 3 = Me，Et，Pr i 已成功应用，并在此处进行了详细说明。
• Haloacetylated enol ethers.<b>14</b>[6]. Reaction of β-alkoxyvinyl trifluoromethyl ketones with<i>N</i>-methylhydroxylamine
  作者：Marcos A. P. Martins、Alex F. C. Flores、Giovani P. Bastos、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1002/jhet.5570360402

  日期：1999.7

  The reaction of a series of β-methoxyvinyl trifluoromethyl ketones [CF3COC(R2)C(OMe)R1, where R1 = Me, -(CH2)3-C3, -CH2)4-C3, Ph and R2 = H, Me, -(CH2)3-C4, -(CH2)4-C4] with N-methylhydroxylamine is reported. The regiochemistry of the reaction are explained by MO calculation data.

  一系列β-甲氧基乙烯基三氟甲基酮[CF 3 COC（R 2）C（OMe）R 1的反应，其中R 1 = Me，-（CH 2）3 - C 3，-CH 2）4 - C 3中，Ph和R 2 = H，Me中， - （CH 2）3 - ç 4， - （CH 2）4 - C ^ 4] ñ -methylhydroxylamine报道。反应的区域化学由MO计算数据解释。
• General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues
  作者：Helio G. Bonacorso、Rosália Andrighetto、Nícolas Krüger、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.3390/molecules16042817

  日期：——

  A convenient and general method for the synthesis in 26–73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, where R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild

  从 4-烷氧基-的直接环缩合反应合成新系列 7-烷基（芳基/杂芳基）-2-氨基-5-三氟甲基-1,8-萘啶的简便通用方法，产率为 26-73% 1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, 其中 R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4描述了 -BrPh、4-NO2Ph、2-呋喃基、2-噻吩基和 R = Me, Et] 与 2,6-二氨基吡啶 (2,6-DAP) 在温和条件下的反应。另一种合成路线还允许从五、六和七的直接或间接环缩合反应合成 2-氨基-5-三氟甲基-环烷[b][1,8]萘啶，产率为 33-36%。 2-三氟乙酰基-1-甲氧基-环烯烃与 2,6-DAP。
• ClickEnam. 1. Synthesis of novel 1,4-disubsituted-[1,2,3]-triazole-derived β-aminovinyl trifluoromethylated ketones and their copper(II) complexes
  作者：Nicolas Chopin、Sophie Decamps、Aude Gouger、Maurice Médebielle、Stéphane Picot、Anne-Lise Bienvenu、Guillaume Pilet

  DOI：10.1016/j.jfluchem.2011.05.011

  日期：2011.10

  The copper(I) catalyzed cycloaddition reaction of N-Boc propargyl amine (dipolarophile) 1 with benzyl azide (1,3-dipole) 2 was found to proceed smoothly in t-BuOH/H2O at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]-triazole-derived N-Boc amine 3 in good yield. Deprotection of 3 with trifluoroacetic acid and addition of the trifluoroacetate salt 4 in the presence of triethylamine, with a series of methoxyvinyl(trifluoromethyl)ketones 10-14, gave the corresponding beta-aminovinyl trifluormethylated ketones 15-19 in moderate to good yields. Two copper(II) complexes, one monomer and one dimer with chlorine double bridge, 20 and 21, respectively, were also prepared and their crystal structure determined. beta-Aminovinyl trifluoromethylated ketones 15-17 and complexes 20 and 21 have been screened as potential antifungal agents and the antimalarial activity of 15 and 16 were tested against two Plasmodium falciparum strains (3D7 and W2). (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis of Tetrahydro‐2(1<i>H</i>)quinazolinones, Cyclopenta[<i>d</i>]‐2(1<i>H</i>)pyrimidinones, and Their Thioxo Analogs from 2‐Trifluoroacetyl‐1‐methoxycycloalkenes
  作者：Helio G. Bonacorso、Michelle B. Costa、Itamar S. Lopes、Marlí R. Oliveira、Roberta L. Drekener、Marcos A. P. Martins、Nilo Zanatta、Alex F. C. Flores

  DOI：10.1080/00397910500278818

  日期：2005.12

  A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1H)pyrimidinones, and their thioxo analogs from the reaction of five beta-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield.