1-phenyl-3-(4-pentylphenyl)-2-propyn-1-one | 1616956-45-6

• 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-phenyl-3-(4-pentylphenyl)-2-propyn-1-one
• 英文别名: 3-(4-pentylphenyl)-1-phenylprop-2-yn-1-one
• CAS: 1616956-45-6
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: UFABHUYNNNEDTG-UHFFFAOYSA-N

物化性质

• 熔点：
  52.4-54.3 °C
• 沸点：
  406.1±38.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(4-pentylphenyl)-2-propyn-1-one 在 吡啶 、 四丁基溴化铵 、 palladium diacetate 、 sodium sulfate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 4-allyl-5-(4-pentylphenyl)-3-phenylisoxazole
  参考文献：
  名称：

  钯催化的烯丙基肟与烯丙基卤化物的级联环化/烯丙基化：快速获得完全取代的异恶唑

  摘要：

  已经建立了通过钯催化的炔肟肟醚与烯丙基卤化物的级联环化/烯丙基化反应合成功能化异恶唑的新颖有效方法。本协议显示温和的反应条件，良好的官能团兼容性和方便的操作。此外，进行了可扩展性并且实现了对异恶唑产物的进一步装饰。

  DOI：

  10.1021/acs.joc.9b01593
• 作为产物：
  描述：

  苯甲醛 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 0.5h， 生成 1-phenyl-3-(4-pentylphenyl)-2-propyn-1-one
  参考文献：
  名称：

  Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes

  摘要：

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

  DOI：

  10.1021/jo5008702

文献信息

• Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones
  作者：Yong Wu、Li Zeng、Haoran Li、Yue Cao、Jingcheng Hu、Minghao Xu、Renyi Shi、Hong Yi、Aiwen Lei

  DOI：10.1021/jacs.1c06036

  日期：2021.8.18

  palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism

  使用一氧化碳的氧化羰基化已发展成为对有价值的含羰基化合物有吸引力的工具，而将 CO 与化学计量量的化学氧化剂（尤其是氧气）混合是危险的，并限制了其在放大合成中的应用。通过采用阳极氧化，我们开发了一种电化学钯催化的芳基肼与炔烃的氧化羰基化，被认为是羰基化 Sonogashira 反应的替代补充。将未分割的电池与恒流模式相结合，无氧条件避免了 CO 的爆炸危险。在无铜条件下使用可接近的芳基肼和炔烃可以有效地获得多种炔酮。基于循环伏安法，电化学 Pd(0)/Pd(II) 循环的可能机制被合理化，
• Synthesis and Biological Evaluation of Acetylenic Chalcones as Novel Anti-Inflammatory Agents
  作者：Chengguang Zhao、Jianpeng Feng、Mingming Zuo、Ying Zhang、Jianfeng Zhao、Shanmei Xu、Suqing Zheng、Yali Zhang、Qinqin Tang、Zhongqiu Lu、Guang Liang、Jianmin Zhou

  DOI：10.2174/1573406411666150209122749

  日期：2015.7.24

  37 acetylenic chalcones were designed, synthesized by the Pd/Cu catalyzed Sonogashira coupling reaction, and evaluated for anti-inflammatory activities. A majority of these compounds showed remarkable inhibitions of the expression of inflammatory cytokines in LPS-stimulated macrophages. Six of them demonstrated the dose-dependent inhibition of inflammatory cytokines, and 4f is the most potent antiinflammatory compound. Our results suggest that these active acetylenic chalcones could be further developed as promising candidates for the treatment of inflammatory diseases.

  设计并合成了37种炔烃基查尔酮，采用Pd/Cu催化的Sonogashira偶联反应，并评估其抗炎活性。大多数化合物显示出对LPS刺激的巨噬细胞中炎症细胞因子表达的显著抑制。六种化合物表现出剂量依赖性的炎症细胞因子抑制，4f是最强效的抗炎化合物。我们的结果表明，这些活性炔烃基查尔酮可进一步开发为治疗炎症疾病的有前景候选药物。
• Tandem aza-Michael addition–vinylogous aldol condensation: synthesis of <i>N</i>-bridged pyridine fused quinolones
  作者：Lalitha Gummidi、Altaf Muddassar、Gangavaram V. M. Sharma、V. Murugesh、Surisetti Suresh

  DOI：10.1039/d1ob02087k

  日期：——

  addition–vinylogous aldol condensation strategy for the synthesis of N-bridged pyridine fused quinolone derivatives from quinolones and ynones. The presented tandem transformation features the construction of C–N and CC bonds in a single operation, under transition metal-free conditions. The wide substrate scope and gram scale synthesis of pyridine fused quinolone derivatives expand the synthetic value of

  在此，我们提出了一种串联氮杂-迈克尔加成-乙烯醇醛缩合策略，用于从喹诺酮类和炔诺酮类合成N-桥联吡啶稠合喹诺酮衍生物。所提出的串联转变的特点是在无过渡金属条件下，在一次操作中构建 C-N 和 C C 键。吡啶融合喹诺酮衍生物的广泛底物范围和克级合成扩大了所提出协议的合成价值。
• Regioselective benzannulation of allylic sulfur ylides with ynones: a rapid access to substituted thioanisoles
  作者：Matam Parameshwar、Maneesh Kumar Reddy Singam、Attunuri Nagireddy、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1039/d0cc05436d

  日期：——

  A novel benzannulation of allyl sulfer ylide (ASY) with alkynones is accomplished for highly regioselective formation of multi substituted thioanisoles where ASY was rarely found to be a 3C component as well as a sulphur source.

  一种新颖的烯丙基硫基亚烯（ASY）与炔酮的苯环化反应已成功实现，高度区域选择性地形成了多取代硫苯，其中ASY很少被发现是一种3C组分和硫源。
• Solvent switchable Pd/DNA catalyst in carbonylative Sonogashira coupling
  作者：M. Mart、A.M. Trzeciak

  DOI：10.1016/j.mcat.2020.111124

  日期：2020.10

  Palladium catalysts immobilized on DNA (Pd/DNA) were applied for the first time in the carbonylative Sonogashira coupling, at 1 atm of CO. Different alkynones were obtained with a high yield in DMF. In the presence of water, the selectivity completely changed and diaryl alkynes, typical Sonogashira products, were selectively formed. In addition to Pd/DNA, soluble palladium species also participated

  固定在DNA上的钯催化剂（Pd / DNA）首次在羰基化Sonogashira偶联中以1 atm的CO浓度应用。获得了不同的炔酮，在DMF中的收率很高。在水的存在下，选择性完全改变并且选择性地形成了典型的Sonogashira产物二芳基炔烃。除Pd / DNA外，可溶性钯也参与了催化过程。添加过量DNA后，催化系统的稳定性提高。