3-(4-methoxyphenyl)-1-(o-tolyl)prop-2-yn-1-one | 1202532-06-6

• 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: 3-(4-methoxyphenyl)-1-(o-tolyl)prop-2-yn-1-one
• 英文别名: 3-(4-methoxyphenyl)-1-(2-methylphenyl)prop-2-yn-1-one
• CAS: 1202532-06-6
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: QCPGYJYVLUFFIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(o-tolyl)prop-2-yn-1-one 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到3-(4-甲氧基苯基)萘-1-醇
  参考文献：
  名称：

  Cu(II)-Catalyzed 6π-Photocyclization of Non-6π Substrates

  摘要：

  This research successfully achieved a Cu(II)-catalyzed 6 pi-photocyclization of non-6 pi substrates. The photo-enolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6 pi-photo- facilitates both photoenolization and 6 pi-photocyclization. This research highlighted the tandem reaction strategy and the importance of metal catalysis in photochemistry.

  DOI：

  10.1021/acs.orglett.0c01854
• 作为产物：
  描述：

  对甲苯甲酸 在 N-甲基吗啉 、 palladium diacetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.0h， 生成 3-(4-methoxyphenyl)-1-(o-tolyl)prop-2-yn-1-one
  参考文献：
  名称：

  Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of “Super-Active Esters”

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b01466

文献信息

• Light-enabled, AlCl₃-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes
  作者：Yanbin Zhang、Ruiwen Jin、Guangxing Pan、Hao Guo

  DOI：10.1039/d0cc04636a

  日期：——

  regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported. Upon photoexcitation, o-alkylphenyl alkynyl ketones can be transferred into (E)-photoenols. Thus, a nucleophilic methylene is formed from the non-nucleophilic alkyl. An AlCl3 catalyst can stabilize the (E)-photoenol intermediate and facilitate further intramolecular nucleophilic cyclization

  报道了使用非亲核烷基作为亲核试剂的光活化的AlCl 3催化炔烃的区域选择性分子内亲核环化反应。光激发后，邻烷基苯基炔基酮可以转移到（E）-光烯醇中。因此，由非亲核烷基形成亲核亚甲基。AlCl 3催化剂可以稳定（E）-光烯醇中间体，并促进进一步的分子内亲核环化。DFT计算表明，AlCl 3催化的环化是区域选择性的决定步骤。
• Highly-efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex-catalyzed coupling of acyl chlorides and terminal alkynes for the formation of ynones
  作者：Jun-You Chen、Tze-Chiao Lin、Szu-Chien Chen、Ai-Jan Chen、Chung-Yuan Mou、Fu-Yu Tsai

  DOI：10.1016/j.tet.2009.10.031

  日期：2009.12

  formation of ynones from a variety of acyl chlorides and terminal alkynes catalyzed by a nanosized MCM-41 anchored palladium bipyridyl complex is described herein. Aroyl, heteroaroyl, and alkyl acyl chlorides were easily coupled with terminal alkynes, giving good to high isolated yields in the presence of a very low catalyst loading (0.002–0.1 mol % Pd) in Et3N or diisopropylethylamine at 50 °C. Furthermore

  本文描述了一种高效且实用的方法，该方法由纳米级MCM-41锚定钯联吡啶络合物催化的各种酰氯和末端炔烃形成炔酮。芳酰基，杂芳酰基和烷基酰基氯很容易与末端炔烃偶联，在50°C的Et 3 N或二异丙基乙胺中催化剂负载量极低（0.002-0.1 mol％Pd）的情况下，分离产率高至良好。此外，单批反应的反应规模高达150 mmol，为实际合成应用提供了潜力。离心后，负载的催化剂能够被再循环并重复使用几次，而活性仅略有下降。
• Gold-Catalyzed 1,3-Transposition of Ynones
  作者：Roohollah Kazem Shiroodi、Mohammad Soltani、Vladimir Gevorgyan

  DOI：10.1021/ja504892c

  日期：2014.7.16

  An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.