1-(3-methylphenyl)-3-(4-methylphenyl)prop-2-yn-1-one | 1428781-54-7

• 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-(3-methylphenyl)-3-(4-methylphenyl)prop-2-yn-1-one
• 英文别名: 1-(m-tolyl)-3-(p-tolyl)prop-2-yn-1-one
• CAS: 1428781-54-7
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: DLBQRWQKCMEMOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三甲基(对甲苯乙炔)硅烷 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 1-乙酸基-1,2-苯碘酰-3-(1H)-酮 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 1-(3-methylphenyl)-3-(4-methylphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  选择性羰基-C（sp3）键裂解通过光氧化还原催化构建亚胺，壬酸酯和壬烯

  摘要：

  碳-碳键的裂解/官能化具有合成价值，选择性的羰基-C（sp 3）键的裂解/炔基化在构建酰胺，炔酸和炔酮方面提供了新的视角。这里报道的是第一个通过光氧化还原催化的烷氧基-自由基使羰基-C（sp 3）键裂解/炔基化反应。使用新型环状碘（III）试剂对于从β-羰基醇（包括具有高氧化还原电势（ 相对于MeCN中的SCE而言> 2.2 V））生成β-羰基烷氧基自由基是必不可少的。β-酰胺，β-酯和β-酮醇首次在温和的反应条件下，分别产生了酰胺，amide酸酯和炔酮，具有出色的区域选择性和化学选择性。

  DOI：

  10.1002/anie.201611897

文献信息

• Zinc‐Catalyzed Dehydrogenative Cross‐Coupling of Terminal Alkynes with Aldehydes: Access to Ynones
  作者：Shan Tang、Li Zeng、Yichang Liu、Aiwen Lei

  DOI：10.1002/anie.201509042

  日期：2015.12.21

  Because of the lack of redox ability, zinc has seldom been used as a catalyst in dehydrogenative cross‐coupling reactions. Herein, a novel zinc‐catalyzed dehydrogenative C(sp2)H/C(sp)H cross‐coupling of terminal alkynes with aldehydes was developed, and provides a simple way to access ynones from readily available materials under mild reaction conditions. Good reaction selectivity can be achieved

  由于缺乏氧化还原能力，锌很少被用作脱氢交叉偶联反应的催化剂。本文中，开发了一种新型的锌催化脱氢炔烃与醛的C（sp 2）H / C（sp）H交叉偶联，并提供了一种在温和的反应条件下从易得的材料中获得炔酮的简单方法。末端炔烃和醛的比例为1：1时，可以实现良好的反应选择性。各种末端炔烃和醛均适用于该转化。
• 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。
• Pd/BaSO₄-catalyzed cross coupling of acyl chlorides with in situ generated alkynylzinc derivatives for the synthesis of ynones
  作者：Hu Yuan、Huizi Jin、Bo Li、Yunheng Shen、Rongcai Yue、Lei Shan、Qingyan Sun、Weidong Zhang

  DOI：10.1139/cjc-2012-0444

  日期：2013.5

  An efficient and operationally simple procedure using Pd/BaSO₄-catalyzed cross coupling of acyl chlorides with in situ generated alkynylzinc derivatives was developed, giving the corresponding ynones at yields of 50%–96%.

  使用Pd/BaSO₄催化的酰氯与原位生成的炔基锌衍生物进行交叉偶联的高效简便程序已开发，产率为50%–96%，得到相应的炔酮。
• Addition of Terminal Alkynes to Aromatic Nitriles Catalyzed by Divalent Lanthanide Amides Supported by Amidates: Synthesis of Ynones
  作者：Bei Zhao、Yingming Yao、Hao Ding、Chengrong Lu、Xiaolin Hu、Bing Wu

  DOI：10.1055/s-0033-1338446

  日期：——

  An efficient protocol has been established for the synthesis of conjugated ynones via addition of terminal alkynes to aromatic nitriles, which is catalyzed by novel divalent lanthanide amide complexes. All the reactions gave the products in good to excellent yields at room temperature under solvent-free conditions without any additives. The novel lanthanide amide catalysts were also synthesized and

  已经建立了通过将末端炔烃添加到芳香腈来合成共轭炔酮的有效方案，该方法由新型二价镧系元素酰胺配合物催化。所有反应均在室温、无溶剂条件下、不含任何添加剂的情况下均以良好至极好的收率得到产物。还首次合成了新型镧系酰胺催化剂并对其进行了结构表征。
• Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of “Super-Active Esters”
  作者：Bo Yu、Huaming Sun、Zunyuan Xie、Guofang Zhang、Li-Wen Xu、Weiqiang Zhang、Ziwei Gao

  DOI：10.1021/acs.orglett.5b01466

  日期：2015.7.2

  A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a dean-and efficient synthetic protocol for a broad array Of ynone compounds under CO-, Cu-,, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron;withdrawing ability and the unique affinity of triazine On palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation.