1-(4-methoxyphenyl)-4,4-dimethylpent-2-yn-1-one | 603126-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-methoxyphenyl)-4,4-dimethylpent-2-yn-1-one
• 英文别名: 4,4-dimethyl-1-(4-methoxyphenyl)-2-pentyn-1-one；2-Pentyn-1-one, 1-(4-methoxyphenyl)-4,4-dimethyl-
• CAS: 603126-38-1
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: UTPNVHJXOLDLHO-UHFFFAOYSA-N

物化性质

• 沸点：
  329.2±44.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-4,4-dimethylpent-2-yn-1-one 在 吡啶 、 bis(acetylacetonato)palladium(II) 、 copper(l) iodide 、 一氯化碘 、 sodium sulfate 、 二乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-(tert-butyl)-3-(4-methoxyphenyl)-4-(phenylethynyl)isoxazole
  参考文献：
  名称：

  通过 Pd 催化的 Sonogashira 交叉偶联反应合成 C4-炔基异恶唑†

  摘要：

  描述了 Pd 催化的 Sonogashira 交叉偶联反应，用于从 3,5-二取代-4-碘异恶唑和末端炔烃合成 C4-炔基异恶唑，该反应可以以高收率（高达 98%）提供相应的产物。结果表明异恶唑C3位基团的空间位阻效应对交叉偶联反应的影响大于C5位基团的空间位阻效应。此外，异恶唑C3位的基团对交叉偶联反应的电子效应可忽略不计。此外，还研究了 Sonogashira 偶联反应的克级反应。最后，提出了 Sonogashira 偶联反应的合理机制。

  DOI：

  10.1039/c9ra00577c
• 作为产物：
  描述：

  [3,3-dimethylbut-1-ynyl(phenyl)-λ3-iodanyl] 4-methoxybenzoate 生成 1-(4-methoxyphenyl)-4,4-dimethylpent-2-yn-1-one
  参考文献：
  名称：

  STANG P. J.; BOEHSHAR M.; LIN JING, J. AMER. CHEM. SOC., 108,(1986) N 24, 7832-7834

  摘要：

  DOI：

文献信息

• Aqueous Ammonia as a New Activator for Sonogashira Coupling
  作者：Mohamed S. Mohamed Ahmed、Akitoshi Sekiguchi、Kentaro Masui、Atsunori Mori

  DOI：10.1246/bcsj.78.160

  日期：2005.1

  Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.

  Sonogashira偶联反应，是一种端炔与有机卤化物的偶联反应，在稀释的氨水溶液中作为活化剂的情况下进行。在室温下，少量过量的氨水存在时，几种端炔与芳基碘的反应能以良好的至极佳的产率得到交叉偶联产物。另一种选择是在较高温度下的反应中使用高沸点的水溶性胺。类似的在二氧化碳存在下的偶联反应也能在室温和常压下高效地进行，生成α,β-炔基酮。
• Pd-Catalyzed Copper-Free Carbonylative Sonogashira Reaction of Aryl Iodides with Alkynes for the Synthesis of Alkynyl Ketones and Flavones by Using Water as a Solvent
  作者：Bo Liang、Mengwei Huang、Zejin You、Zhengchang Xiong、Kui Lu、Reza Fathi、Jiahua Chen、Zhen Yang

  DOI：10.1021/jo050498t

  日期：2005.7.1

  Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent. The reaction was carried out at room temperature under balloon pressure of CO with Et3N as a base. The developed method was successfully applied to the synthesis of flavones.

  钯催化的无铜羰基化Sonogashira偶联反应，是通过用水为溶剂，由末端炔烃和芳基碘化物合成炔基酮的。反应在室温下以Et 3 N为碱在CO的球囊压力下进行。所开发的方法已成功地应用于黄酮的合成。
• Recyclable and reusable PdCl2(PPh3)2/PEG-2000/H2O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
  作者：Hong Zhao、Mingzhu Cheng、Jiatao Zhang、Mingzhong Cai

  DOI：10.1039/c3gc42278j

  日期：——

  PdCl2(PPh3)2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 °C with Et3N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o-iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl2(PPh3)2/PEG-2000/H2O system can be easily recycled and reused six times without any loss of catalytic activity.

  在水和聚乙烯醇（PEG-2000）的混合物中，PdCl2(PPh3)2被证明是一种极为活跃的催化剂，可以催化芳基碘与末端炔烃的羰基化索诺加希拉偶合反应。该反应可以在25 °C、用三乙胺作为碱的情况下，在常压的二氧化碳气氛下进行，结果得到多种炔基酮，产率良好至优异。采用这种合成方法还能成功将邻碘苯酚与末端炔烃转化为黄酮。产品的分离通过二乙醚提取即可轻松实现，PdCl2(PPh3)2/PEG-2000/H2O体系可轻松回收并重复使用六次，且没有任何催化活性损失。
• Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles
  作者：Xiujuan Feng、Jiliang Song、Ming Bao

  DOI：10.1002/jccs.201700302

  日期：2018.3

  synthesis of α,β‐alkynyl ketones from the three‐component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β‐alkynyl ketones in good to excellent yields.

  成功开发了一种由芳基碘化物，末端炔烃和一氧化碳的三组分偶合（羰基Sonogashira偶合反应）合成α，β-炔基酮的简便有效的方法。羰基Sonogashira偶联反应在钯纳米粒子存在的条件下在温和条件下平稳进行，可产生相应的α，β-炔基酮，收率良好。
• Copper-Catalyzed Cross- and Carbonylative Coupling Reactions of ­Alkynyliodonium Salts with Organoboronic Acids and Organostannanes
  作者：Chan-Mo Yu、Jae-Hong Kweon、Pil-Su Ho、Sin-Cheol Kang、Gong Yeal Lee

  DOI：10.1055/s-2005-918934

  日期：——

  Copper-catalyzed cross- and carbonylative coupling ­reactions have been achieved in the reaction of a variety of alkynyl­iodonium salts with arylboronic acids and organostannanes under the mild reaction conditions in high yield. Our investigation shows that the alkynylidonium tetrafluoroborates are more efficient than those of triflates and tosylates.

  铜催化的交叉和羰基化偶联反应已成功实现，反应中多种炔基碘鎓盐与芳基硼酸和有机锡化合物在温和的反应条件下高产率反应。我们的研究表明，炔基碘鎓四氟硼酸盐的效率优于三氟甲磺酸盐和对甲苯磺酸盐。