1-[4-(dimethylamino)phenyl]-3-phenylprop-2-yn-1-one | 112539-33-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-[4-(dimethylamino)phenyl]-3-phenylprop-2-yn-1-one
• CAS: 112539-33-0
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: APFNNJQWMHTJPU-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  414.2±47.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(dimethylamino)phenyl]-3-phenylprop-2-yn-1-one 在 叠氮基三甲基硅烷 作用下， 以 三氯乙烯 为溶剂， 反应 12.0h， 以70%的产率得到N,N-dimethyl-4-(3-phenylisoxazol-5-yl)aniline
  参考文献：
  名称：

  A direct access to isoxazoles from ynones using trimethylsilyl azide as amino surrogate under metal/catalyst free conditions

  摘要：

  描述了一种从易得的炔酮中使用三甲基硅基叠氮作为氨代用体，在异常简单的条件下获得异噁唑并具有出色的官能团兼容性的一般方法。

  DOI：

  10.1039/c6cc02047j
• 作为产物：
  描述：

  1-(4-(dimethylamino)phenyl)-3-phenylprop-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以2.13 g的产率得到1-[4-(dimethylamino)phenyl]-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  亲电环化合成高取代异恶唑：一种有效合成伐地昔布

  摘要：

  大量官能取代的 2-alkyn-1-one O-甲基肟在温和的反应条件下在 ICl 存在下环化，以中等至极好的收率得到相应的 4-碘异恶唑。所得的 4-碘异恶唑经过各种钯催化反应生成 3,4,5-三取代的异恶唑，包括伐地考昔。

  DOI：

  10.1021/jo701942e

文献信息

• A General and Convenient Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides
  作者：Xiao-Feng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201001864

  日期：2010.10.25

  Convenient carbonylations: An efficient methodology for the carbonylative Sonogashira reaction of aryl bromides has been developed (see scheme). Contrary to known procedures, inexpensive aryl bromides can be applied as substrates to give the desired compounds in moderate to good yields (47–88 %).

  方便的羰基化：已开发出一种有效的方法用于芳基溴的羰基化Sonogashira反应（请参见方案）。与已知方法相反，廉价的芳基溴化物可以用作底物，以中等至良好的收率（47–88％）得到所需化合物。
• Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1<i>H</i>-pyridines by Michael addition–cyclocondensation sequences
  作者：Natascha Breuer、Irina Gruber、Christoph Janiak、Thomas J J Müller

  DOI：10.3762/bjoc.15.262

  日期：——

  Starting from substituted alkynones, α-pyrones and/or 1H-pyridines were generated in a Michael addition–cyclocondensation with ethyl cyanoacetate. The peculiar product formation depends on the reaction conditions as well as on the electronic substitution pattern of the alkynone. While electron-donating groups furnish α-pyrones as main products, electron-withdrawing groups predominantly give the corresponding 1H-pyridines. Both heterocycle classes fluoresce in solution and in the solid state. In particular, dimethylamino-substituted α-pyrones, as donor–acceptor systems, display remarkable photophysical properties, such as strongly red-shifted absorption and emission maxima with daylight fluorescence and fluorescence quantum yields up to 99% in solution and around 11% in the solid state, as well as pronounced emission solvatochromism. Also a donor-substituted α-pyrone shows pronounced aggregation-induced emission enhancement.

  从取代炔酮出发，通过乙基氰乙酸酯的Michael加成-环缩合反应生成α-吡喃酮和/或1H-吡啶。独特的产物形成取决于反应条件以及炔酮的电子取代模式。虽然电子给予基团提供α-吡喃酮作为主要产物，但电子提取基团主要给出相应的1H-吡啶。这两类杂环在溶液和固态中均发出荧光。特别是二甲氨基取代的α-吡喃酮作为给体-受体系统，显示出显著的光物理性质，如强烈的红移吸收和发射最大值，具有日光荧光和溶液中高达99%的荧光量子产率，固态中约为11%，以及明显的发射溶剂致色变。此外，给体取代的α-吡喃酮显示出明显的聚集诱导发射增强。
• Novel Fluorescent Aluminum Complexes Based on<i>N</i>-Hydroxy-3,6-diaryl-4-phenyl-2-pyridone Ligands
  作者：Satoshi Minakata、Hiroshi Inada、Mitsuo Komatsu、Hirotake Kajii、Yutaka Ohmori、Manabu Tsumura、Kiyoyuki Namura

  DOI：10.1246/cl.2008.248

  日期：2008.3.5

  Novel fluorescent aluminium complexes of N-hydroxy-3,6-diaryl-4-phenyl-2-pyridone derivatives were synthesized and their fluorescent properties were investigated. The complexes having a trifluoromethyl group and a methoxy group at the para-position on the 3- and 6-phenyl groups exhibit purple fluorescence in the solid state.

  合成了N-羟基-3,6-二芳基-4-苯基-2-吡啶酮衍生物的新型荧光铝复合物，并研究了它们的荧光特性。这些在3-和6-苯基的对位上具有三氟甲基和甲氧基的复合物在固态下表现出紫色荧光。
• Synthesis and Spectroscopic Properties of New Fluorescent 3,6-Diaryl-4-phenyl-2-pyridone Derivatives
  作者：Satoshi Minakata、Shouta Moriwaki、Hiroshi Inada、Mitsuo Komatsu、Hirotake Kajii、Yutaka Ohmori、Manabu Tsumura、Kiyoyuki Namura

  DOI：10.1246/cl.2007.1014

  日期：2007.8.5

  Novel fluorescent 3,6-diaryl-4-phenyl-2-pyridone derivatives were synthesized and their fluorescent properties were investigated. These compounds emit intense brilliant blue fluorescence only in the solid state, not in solution. An electron-donating substituent on the 6-phenyl group caused a red-shift in fluorescence maxima.

  合成了新型荧光3,6-二芳基-4-苯基-2-吡啶酮衍生物，并研究了它们的荧光性质。这些化合物仅在固态时发射强烈的鲜蓝色荧光，而在溶液中则不发射。6-苯基上的电子供体取代基会导致荧光最大值红移。
• Room Temperature ICl-Induced Dehydration/Iodination of 1-Acyl-5-hydroxy-4,5-dihydro-1<i>H</i>-pyrazoles. A Selective Route to Substituted 1-Acyl-4-iodo-1<i>H</i>-pyrazoles
  作者：Jesse P. Waldo、Saurabh Mehta、Richard C. Larock

  DOI：10.1021/jo800789p

  日期：2008.9.1

  functionally substituted 1-acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles have been prepared in moderate to excellent yields from the corresponding 2-alkyn-1-ones. The resulting dihydropyrazoles undergo dehydration and iodination in the presence of ICl and Li2CO3 at room temperature to provide 1-acyl-4-iodo-1H-pyrazoles.

  已经从相应的 2-alkyn-1-ones 以中等至极好的收率制备了许多新的功能取代的 1-acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles。所得二氢吡唑在室温下在 ICl 和 Li2CO3 存在下进行脱水和碘化，以提供 1-酰基-4-碘-1H-吡唑。