反式,反式-1,5-双[4-(三氟甲基)苯基]-1,4-戊二烯-3-酮 | 103836-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 反式,反式-1,5-双[4-(三氟甲基)苯基]-1,4-戊二烯-3-酮
• 英文名称: 1,5-bis-(4'-trifluoromethylphenyl)-penta-1E,4E-dien-3-one
• 英文别名: 1,5-bis(4-trifluoromethylphenyl)-1,4-pentadien-3-one；(1E,4E)-1,5-di(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-one；(1E,4E)-1,5-bis(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-one；trans,trans-bis(4-trifluoromethylbenzal)acetone；1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadiene-3-one；1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadien-3-one；Trans,trans-1,5-Bis[4-(trifluoromethyl)phenyl]-1,4-pentadien-3-one；(1E,4E)-1,5-bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one
• CAS: 103836-71-1
• 化学式: C₁₉H₁₂F₆O
• 分子量: 370.294
• InChiKey: OIUBVYQZMUKRRF-YDWXAUTNSA-N

物化性质

• 熔点：
  129-130 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  402.2±45.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  388nm(THF)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P301+P310
• 危险品运输编号：
  2811
• 危险性描述：
  H301
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  反式,反式-1,5-双[4-(三氟甲基)苯基]-1,4-戊二烯-3-酮 在 吡啶 、 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 0.08h， 生成 N-((1E,4E)-1,5-bis(4-(trifluoromethyl)phenyl)penta-1,4-dien-3-ylidene)aniline oxide
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated N-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free N-Arylation Process

  摘要：

  An efficient transition-metal-free method for the preparation of alpha,beta-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.

  DOI：

  10.1021/acs.joc.5b01716
• 作为产物：
  描述：

  Hydramethylnon 生成 反式,反式-1,5-双[4-(三氟甲基)苯基]-1,4-戊二烯-3-酮
  参考文献：
  名称：

  MALLIPUDI N. MOORTHY; STOUT S. J.; LEE AN-HORNG; ORLOSKI E. J., J. AGR. AND FOOD CHEM., 34,(1986) N 6, 1050-1057

  摘要：

  DOI：

文献信息

• Regioselective mono-aza-Michael additions of divinyl ketones with 3-(arylimino)indolin-2-ones: Synthesis of N-enone-functionalized 3-(arylimino)indolin-2-ones
  作者：Xiao Chen、Zheng Li

  DOI：10.1177/1747519820920179

  日期：2020.11

  Selective mono-aza-Michael additions of divinyl ketones with 3-(arylimino)indolin-2-ones in the presence of cesium carbonate are described. N-Enone-functionalized 3-(arylimino)indolin-2-ones were efficiently synthesized in satisfactory yield. The salient features of this protocol are high regioselectivity, high yield, and mild conditions.

  描述了在碳酸铯存在下二乙烯基酮与 3-(芳基亚氨基)indolin-2-ones 的选择性单氮杂-迈克尔加成。N-烯酮官能化的 3-(芳基亚氨基) indolin-2-ones 以令人满意的产率有效合成。该协议的显着特点是高区域选择性、高产率和温和的条件。
• Palladium(II)-Catalyzed Substituted Pyridine Synthesis from α,β-Unsaturated Oxime Ethers via a C–H Alkenylation/Aza-6π-Electrocyclization Approach
  作者：Takahiro Yamada、Yoshimitsu Hashimoto、Kosaku Tanaka、Nobuyoshi Morita、Osamu Tamura

  DOI：10.1021/acs.orglett.1c00061

  日期：2021.3.5

  for multisubstituted pyridines from β-aryl-substituted α,β-unsaturated oxime ethers and alkenes via Pd-catalyzed C–H activation has been developed. Systematic optimization of catalyst ligands revealed that sterically hindered pyridines increased the reactivity. Mechanistic studies suggested that the products are formed by Pd-catalyzed β-alkenylation of α,β-unsaturated oxime followed by aza-6π-electrocyclization

  已经开发了一种有效的合成方法，可通过Pd催化的CH活化从β-芳基取代的α，β-不饱和肟醚和烯烃中合成多取代的吡啶。催化剂配体的系统优化表明，位阻吡啶可提高反应活性。机理研究表明，产物是由Pd催化α，β-不饱和肟的β-烯基化，然后进行aza-6π-电环化而形成的。可以使用各种肟和烯烃来提供具有完全区域选择性的多取代吡啶。该方法的有用性通过4-芳基取代的吡啶衍生物的合成得到了证明，这是以前报道的用烯烃进行的Rh催化方法难以获得的。
• The Elusive Structure of Pd₂(dba)₃. Examination by Isotopic Labeling, NMR Spectroscopy, and X-ray Diffraction Analysis: Synthesis and Characterization of Pd₂(dba-Z)₃Complexes
  作者：Anant R. Kapdi、Adrian C. Whitwood、David C. Williamson、Jason M. Lynam、Michael J. Burns、Thomas J. Williams、Alan J. Reay、Jordan Holmes、Ian J. S. Fairlamb

  DOI：10.1021/ja403259c

  日期：2013.6.5

  differential catalytic performance in an eclectic array of cross-coupling reactions. The precise structure of these types of complexes has been confounding, since early studies in 1970s to the present day. In this study the solution and solid-state structures of Pd(0)2(dba)3 and Pd(0)2(dba-Z)3 have been determined. Isotopic labeling ((2)H and (13)C) has allowed the solution structures of the freely

  Pd(0)2(dba)3（dba = E,E-二亚苄基丙酮）是 Pd 介导的转化中使用最广泛的 Pd(0) 源。Pd(0)2(dba-Z)3（Z = dba 芳基取代基）配合物在一系列不拘一格的交叉偶联反应中表现出显着且差异化的催化性能。从 1970 年代的早期研究到现在，这些类型的复合物的精确结构一直令人困惑。在这项研究中，已经确定了 Pd(0)2(dba)3 和 Pd(0)2(dba-Z)3 的溶液和固态结构。同位素标记 ((2)H 和 (13)C) 允许在高场 (700 MHz) 下确定 Pd(0)2(dba)3 的自由交换主要和次要异构体的溶液结构。DFT 计算支持实验确定的主要和次要异构结构，这表明 Pd(0)2(dba)3 的主要异构体具有仅在 s-cis,s-trans 构象中发现的桥连 dba 配体。对于次要异构体，发现 dba 配体之一仅在 s-trans,s-trans
• Lewis acid mediated diastereoselective synthesis of fused fluorinated spiroketal as potential biologically active compounds
  作者：Oluropo C. Agbaje、Olugbeminiyi O. Fadeyi、Cosmas O. Okoro

  DOI：10.1016/j.tetlet.2011.08.004

  日期：2011.10

  A series of substituted dibenzalacetones prepared using standard procedures were condensed with 5-methyl, 5-phenyl, and 5-trifluoromethyl-1,3-cyclohexanediones respectively, in toluene containing BF3·OEt as the Lewis acid catalyst. The reaction was found to be highly diastereoselective (dr, 9:1). The resulting spiroketals 1a–r were formed in moderate to good yields. In addition, a synthetically and

  在含有BF 3 ·OEt作为路易斯酸催化剂的甲苯中，将按标准方法制备的一系列取代的二苯甲丙酮分别与5-甲基，5-苯基和5-三氟甲基-1,3-环己烷二酮缩合。发现该反应是高度非对映选择性的（dr，9：1）。形成的螺帽1a – r以中等至良好的产量形成。另外，观察到鉴定为色酮7的合成和生物学上有用的副产物。
• COMPOUNDS USEFUL AGAINST KINETOPLASTIDEAE PARASITES
  申请人：Davioud-Charvet Elisabeth

  公开号：US20120214996A1

  公开（公告）日：2012-08-23

  Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.

  二苄基亚烷和杂二苄基亚烷乙酮衍生物，相关的4-哌啶酮，相关的4-噻opyranones以及相应的亚磺酰基和磺酰基类似物，用于预防或治疗锥虫病和利什曼病。