4-methoxy-4-phenyl-1,1,1-trichlorobut-3-en-2-one | 156519-20-9

• 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
• 英文名称: 4-methoxy-4-phenyl-1,1,1-trichlorobut-3-en-2-one
• 英文别名: 4-methoxy-4-phenyl-1,1,1-trichloro-3-buten-2-one；1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one；1,1,1-trichloro-4-methoxy-4-phenylbut-3-en-2-one
• CAS: 156519-20-9
• 化学式: C₁₁H₉Cl₃O₂
• 分子量: 279.55
• InChiKey: SDZUUSJFEZWWPU-UHFFFAOYSA-N

物化性质

• 沸点：
  311.6±42.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-4-phenyl-1,1,1-trichlorobut-3-en-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 70.0 ℃ 、220.0 kPa 条件下， 生成 3-phenyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Microwave-assisted synthesis and antimicrobial activity of 5-trihalomethyl-3-arylisoxazoles

  摘要：

  A series of twelve 5-trihalomethyl-3-arylisoxazoles was synthesized and screened for antibacterial and antifungal activities. The compounds were synthesized from the cyclondensation of 1,1,1-trihalo-4-alkoxy-3-alken-2-ones [CX C-3(O)C(R-2)=C(R-1)OR, where X = Cl and F; R=Me; R-2=H; R-1=H, Me, F, Cl, Br, and NO2] with hydroxylamine hydrochloride through a rapid one-pot reaction via microwave irradiation. Some of the 5-trihalomethyl-3-arylisoxazoles exhibited good in vitro anti-Cryptococcus activity.

  DOI：

  10.1007/s00706-007-0849-1
• 作为产物：
  描述：

  (1,1-二甲氧基乙基)苯 、 三氯乙酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 8.0h， 生成 4-methoxy-4-phenyl-1,1,1-trichlorobut-3-en-2-one
  参考文献：
  名称：

  Synthesis and Structure of Novel 1-Aryl-4,4,4-trichloro-1,3-butanediones

  摘要：

  Novel 1-aryl-4,4,4-trichloro-1,3-butanediones in good yields (80-97%) were synthesized in one pot through acetal acylation with trichloroacetyl chloride followed by acid hydrolysis. Structures of all compounds were elucidated by elemental analysis, mass spectrometry, and H-1/C-13 nuclear magnetic resonance (NMR) measurements. The H-1/C-13 NMR data showed that trichloromethyl-beta-diketones 2a-k in solution are predominantly ketoenol. However, the spectroscopic data from 4,4,4-trichloro-2-methyl-1-phenyl-1,3-butabedione (2l) with methyl substituent between carbonyls showed a bias toward the diketo form in solution. X-ray diffraction of monocrystals from 2g and 2i showed that these compounds are cis-ketoenol tautomers.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communcations (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2010.530376

文献信息

• Synthesis of pyrazolo[1,5-a]quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions
  作者：Carson Wiethan、Steffany Z. Franceschini、Helio G. Bonacorso、Mark Stradiotto

  DOI：10.1039/c6ob01407k

  日期：——

  pyrazolo[1,5-a]quinoxalin-4(5H)-ones from easily prepared 1-(2-chlorophenyl-5-ethylcarboxylate)pyrazoles and various primary alkylamines is described. The key steps involved in the synthesis of the new 5,6-fused ring system are the formation of an amide intermediate followed by an intramolecular N-arylation reaction via nucleophilic aromatic substitution.

  从容易制备的1-（2-氯苯基-5-乙基羧酸）吡唑和各种伯酸酯合成新的吡唑并[1,5 - a ]喹喔啉-4（5 H）-的有效的一锅无过渡金属方法描述了烷基胺。新的5，6-稠合环系统合成中涉及的关键步骤是形成酰胺中间体，然后通过亲核芳族取代进行分子内N-芳基化反应。
• One-pot synthesis of aryl and heteroaroyl-substituted hydroxypyrazolines from the reactions of β-alkoxyvinyl trichloromethyl ketones with heteroarylhydrazides
  作者：Helio G. Bonacorso、Marli R. Oliveira、Michelle B. Costa、Roberta L. Drekener、Letícia B. da Silva、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1002/hc.20261

  日期：——

  synthesis of a novel series of 10 trichloromethyl-, aryl-, and heteroaroyl-substituted 5-hydroxy-2-pyrazolines affords 1-(2-thenoyl)-, 1-(2-furoyl)-, and 1-(isonicotinoyl)-3-aryl-5-hydroxy-5-trichloromethyl-4,5-dihydro-1H-pyrazoles in 63–92% yields from the cyclocondensation reactions of 1,1,1-trichloro-4-methoxy-4-aryl-3-buten-2-ones (where aryl substituents are –C6H5, 4-CH3C6H4, 4-OCH3C6H4, 4-FC6H4,

  10 个三氯甲基-、芳基-和杂芳酰基-取代的 5-羟基-2-吡唑啉的新型系列的一步区域特异性合成提供 1-(2-thenoyl)-、1-(2-furoyl)-和 1 -(异烟酰基)-3-芳基-5-羟基-5-三氯甲基-4,5-二氢-1H-吡唑，1,1,1-三氯-4-甲氧基-4的环缩合反应产率为63-92% -芳基-3-丁烯-2-酮（其中芳基取代基为-C6H5、4-CH3C6H4、4-OCH3C6H4、4-FC6H4、4-ClC6H4、4-BrC6H4）与2-噻吩甲酰肼、呋喃酰肼和异烟酸分别为酰肼。两种 2-吡唑啉与 P2O5 的脱水反应以低产率 (21-29%) 提供相应的 1H-吡唑。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:685–691, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI
• New efficient approach for the synthesis of 2-alkyl(aryl) substituted 4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidin-4-ones
  作者：Helio G. Bonacorso、Fernando J. Righi、Isadora R. Rodrigues、Cleber A. Cechinel、Michelle B. Costa、Arci D. Wastowski、Marcos A. P. Martins、Nilo Zanatta

  DOI：10.1002/jhet.5570430136

  日期：2006.1

  A new, efficient and easy route for the preparation of a series of 2-alkyl(aryl) substituted 4-oxo-4H-pyrido-[1,2-a]pyrimidines, where alkyl = CH3; aryl = C6H5, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-CH3C6H4, 4-OCH3C6H4, 4-NO2C6H4 in 45–80 % yield from the reaction of β-alkoxyvinyl trichloromethyl ketones with 2-aminopyridine under mild conditions, is then reported.

  一系列2-烷基（芳基）的制备一种新的，有效的和简单的路线被取代的4-氧代-4- ħ -pyrido- [1,2一]嘧啶类，其中烷基= CH 3 ; 芳= C 6 H ^ 5，4-FC 6 H ^ 4，4-CLC 6 ħ 4，4- BRC 6 ħ 4，4-CH 3 C ^ 6 ħ 4，4-OCH 3 C ^ 6 ħ 4，4-NO 2 C 6高4 据报道，在温和的条件下，β-烷氧基乙烯基三氯甲基酮与2-氨基吡啶的反应收率为45-80％。
• Haloacetylated enol ethers.<b>13</b>. Synthesis of<i>N</i>-[1-aryl(alkyl)-3-oxo-4,4,4-trichloro-1-buten-1-yl]-<i>o</i>-phenylenediamines and 2-trichloromethyl-4-aryl-3<i>H</i>-1,5-benzodiazepines
  作者：Helio Gauze Bonacorso、Sandra R. T. Bittencourt、Arci D. Wastowski、Alexandre P. Wentz、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1002/jhet.5570360108

  日期：1999.1

  The synthesis and isolation of the intermediates N-[1-aryl(alkyl)-3-oxo-4,4,4-trichloro-1-buten-1-yl]-o-phenylenediamines 2a-f and the corresponding 2-trichloromethyl-4-aryl-3H-1,5-benzodiazepines 3c-g or benzimidazoles 4a-b derivatives obtained from the intramolecular cyclization of 2a-f or from direct cyclo-condensation reaction of β-alkoxyvinyl trichloromethyl ketones 1a-g with o-phenylenediamine

  中间体N- [1-芳基（烷基）-3-氧代-4,4,4-三氯-1-丁烯-1-基]-邻苯二胺2a-f和相应的2-三氯甲基的合成和分离-4-芳基-3- ħ -1,5-苯二氮3C-克或苯并咪唑4a-b中从分子内环化得到的衍生物2A-F或从β-烷氧基乙烯基三氯甲基酮的直接环缩合反应1A-G与ö -报道了苯二胺。取决于β-烷氧基乙烯基三氯甲基酮或N- [1-芳基（烷基）-3-氧代-4,4,4-三氯丁烯-1-基] -o的结构获得了苯二胺和反应条件，苯并咪唑或3 H -1,5-苯并二氮杂s。
• New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues
  作者：Helio G. Bonacorso、Maiara C. Moraes、Fábio M. Luz、Pedro S. Quintana、Nilo Zanatta、Marcos A.P. Martins

  DOI：10.1016/j.tetlet.2014.11.125

  日期：2015.1

  This work presents a new synthesis of the antiepileptic drug rufinamide—1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide) in chemical form—and some analogue compounds, through a one-pot reaction employing a solventless, metal-free catalysis and without any reducing reagent. The great novelty presented is the synthesis of 4-trichloroacetyl-1-(2,6-difluorobenzyl/benzyl/4-methoxybenzyl)-5-methyl(phenyl)-1H-1

  这项工作提出了一种抗癫痫药芦丁酰胺的新合成形式-化学形式的1-（2,6-二氟苄基）-1 H -1,2,3-三唑-4-羧酰胺）和一些类似的化合物，锅式反应采用无溶剂，无金属的催化，不需任何还原剂。提出的一个新奇的东西是从苯甲酸合成新的前体物4-三氯乙酰-1-（2,6-二氟苄基/苄基/ 4-甲氧基苄基）-5-甲基（苯基）-1 H -1,2,3-三唑。 1,1,1-三氯-4-烷氧基烷-3-en-2-ones和一些苄基叠氮化物之间的区域选择性1,3-偶极环加成反应，通过与水溶液的加成-消除反应转化为芦丁酰胺和类似物NH 4溶液OH的收率很高（42–52％）。