(E)-1-(4-硝基苯基)戊-1-烯-3-酮 | 54951-55-2

• 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: (E)-1-(4-硝基苯基)戊-1-烯-3-酮
• 英文名称: (E)-1-(p-Nitrophenyl)-1-penten-3-on
• 英文别名: (E)-1-(4-nitrophenyl)pent-1-en-3-one；1t-(4-nitro-phenyl)-pent-1-en-3-one；1t-(4-Nitro-phenyl)-pent-1-en-3-on
• CAS: 54951-55-2
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: UXKOHIVGWGOZBF-VMPITWQZSA-N

物化性质

• 熔点：
  107 °C
• 沸点：
  335.1±17.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-硝基苯基)戊-1-烯-3-酮 生成 (+/-)-5-dimethylamino-4-methyl-1t-(4-nitro-phenyl)-pent-1-en-3-one; hydrochloride
  参考文献：
  名称：

  Mannich Bases from Benzalacetones

  摘要：

  DOI：

  10.1021/ja01154a107
• 作为产物：
  描述：

  对硝基苯甲醛 在 乙醇 、 对甲苯磺酸 、 苯 作用下， 生成 (E)-1-(4-硝基苯基)戊-1-烯-3-酮
  参考文献：
  名称：

  Catalyst Selectivity in the Reactions of Unsymmetrical Ketones; Reaction of Butanone with Benzaldehyde and p-Nitrobenzaldehyde

  摘要：

  DOI：

  10.1021/ja01512a031

文献信息

• Palladium-Catalysed Heck Reactions of Alk-1-en-3-ones with Aryl Bromides: A Very Simple Access to (<i>E</i>)-1-Arylalk-1-en-3-ones
  作者：Mhamed Lemhadri、Yacoub Fall、Henri Doucet、Maurice Santelli

  DOI：10.1055/s-0028-1087976

  日期：——

  When appropriate reaction conditions are used, very high yields of (E)-1-arylalk-1-en-3-one derivatives can be obtained by palladium-catalysed reactions of alk-1-en-3-ones with aryl bromides. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 was found to be a very efficient catalyst for this reaction. In general, higher reaction rates were observed with electron-poor aryl bromides, but the electron-rich aryl bromides 1-bromo-4-(dimethylamino)benzene and 4-bromoanisole also led to the arylated enones in high yields. Even with sterically very congested aryl bromides such as 9-bromoanthracene, 1-bromo-2,4,6-trimethylbenzene or 1-bromo-2,4,6-triisopropylbenzene, the expected (E)-1-arylalk-1-en-3-ones were obtained in moderate to good yields. These enones appear to be unstable under the reaction conditions, and the addition of a small amount of hydroquinone to the reaction mixture was found to be crucial, especially for the vinylation of electron-deficient aryl bromides. A variety of alk-1-en-3-ones has been employed, and better results in terms of substrate/catalyst ratios were obtained when oct-1-en-3-one or hex-1-en-3-one was used than when but-1-en-3-one or pent-1-en-3-one was used. It should be noted that several reactions can be performed with as little as 0.1-0.001 mol% catalyst.

  在适当的反应条件下，通过钯催化的alk-1-en-3-ones与芳基溴化物的反应，可以获得高产率的(E)-1-芳基烯-1-烯-3-酮衍生物。铑催化剂中发现四膦配体顺，顺，顺-1,2,3,4-四(二苯膦甲基)环戊烷与[Pd(C3H5)Cl]2结合是一种非常高效的催化剂。通常情况下，电子贫乏的芳基溴化物显示出更高的反应速率，但电子富集的芳基溴化物1-溴-4-(二甲基氨基)苯和4-溴苯甲醚也能导致高产率的芳基化烯酮。即使在空间位阻很大的芳基溴化物如9-溴蒽、1-溴-2,4,6-三甲基苯或1-溴-2,4,6-三异丙基苯的情况下，期望的(E)-1-芳基烯-1-烯-3-酮也能在中等至良好的产率下获得。这些烯酮在反应条件下似乎是不稳定的，在反应混合物中加入少量的氢醌被发现是至关重要的，特别是对于电子缺乏的芳基溴化物的乙烯基化。已使用了多种alk-1-en-3-ones，当使用辛-1-烯-3-酮或己-1-烯-3-酮时，相对于底物/催化剂比例，得到了更好的结果，而不是丁-1-烯-3-酮或戊-1-烯-3-酮。值得注意的是，有几种反应可以在仅0.1-0.001 mol%催化剂的情况下进行。
• Evaluation of Nuclear‐substituted Styryl Ketones and Related Compounds for Antitumor and Cytotoxic Properties
  作者：J.R. Dimmock、W.G. Taylor

  DOI：10.1002/jps.2600640210

  日期：1975.2

  A number of nuclear-substituted styryl ketones, the related Mannich bases, and allyl alcohols were synthesized and evaluated for antitumor activity, principally in the L-1210 lymphoid leukemia and P-388 lymphocytic leukemia screening tests. The cytotoxicity of some of these compounds assessed in Eagle's 9KB carcinoma cell culture system was also recorded. Two of the Mannich bases showed promising levels

  合成了许多核取代的苯乙烯基酮，相关的曼尼希碱和烯丙醇，并主要在L-1210淋巴白血病和P-388淋巴细胞白血病筛选试验中评估了其抗肿瘤活性。还记录了在Eagle的9KB癌细胞培养系统中评估的某些化合物的细胞毒性。曼尼希（Mannich）的两个碱基在P-388筛选中显示出令人鼓舞的活性水平。在迄今为止获得的结果中，超过三分之一的衍生物在1-3 ppm的剂量水平下显示出细胞毒性。简要报告了这些化合物的其他药理结果。
• One-Pot Synthesis of α,β-Unsaturated Ketones
  作者：Kilsung Lee、Dong Young Oh

  DOI：10.1055/s-1991-26423

  日期：——

  The preparation of α,β-unsaturated ketones is performed in a one-pot procedure by subsequent treatment of diethyl lithiomethyl-phosphonate with nitriles, followed by addition of carbonyl compounds and hydrolysis.

  通过一步法操作，通过随后处理二乙基锂甲基膦酸酯与腈，接着加入羰基化合物并进行水解，完成了α,β-不饱和酮的制备。
• One single catalyst, Pd(OAc)2, for two sequential very different steps: allylic alcohol oxidation–Heck reaction. Access to functionalised α,β-unsaturated ketones
  作者：Frédéric Batt、Christel Gozzi、Fabienne Fache

  DOI：10.1039/b810538c

  日期：——

  A single addition of the catalyst, Pd(OAc)2, was realised to mediate two transformations as different as allylic alcohol oxidation under O2 and C–C bond formation of the Heck type, to give substituted α,β-unsaturated ketones without intermediate purification.

  催化剂 Pd(OAc)2 的单次添加可介导两种不同的转化，如 O2 下烯丙醇氧化和 Heck 型 C-C 键形成，从而得到取代的 α,β-不饱和酮，而无需中间纯化。
• VISHNYAKOVA G. M.; SMIRNOVA T. V., D1-ZH. BCEC. XIM. O-BA IM. D. I. MENDELEEVA, 1978, 23, HO 2, 235-236
  作者：VISHNYAKOVA G. M.、 SMIRNOVA T. V.

  DOI：——

  日期：——