1-(2-methoxyphenyl)-3-(4-methylphenyl)propynone | 767303-57-1

• 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-(2-methoxyphenyl)-3-(4-methylphenyl)propynone
• 英文别名: 1-(2-methoxyphenyl)-3-(p-tolyl)prop-2-yn-1-one；1-(2-Methoxyphenyl)-3-(4-methylphenyl)prop-2-yn-1-one
• CAS: 767303-57-1
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: XBAVWMDXPVFDAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)-3-(4-methylphenyl)propynone 在 水 、 copper diacetate 、 一氯化碘 、 sodium carbonate 、 乙二醇 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 8-methyl-11H-benzofuro[3,2-b]chromen-11-one
  参考文献：
  名称：

  Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source

  摘要：

  A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.

  DOI：

  10.1021/acs.orglett.8b01969
• 作为产物：
  描述：

  4-甲苯基乙炔 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2-methoxyphenyl)-3-(4-methylphenyl)propynone
  参考文献：
  名称：

  通过 2-(3-Aryl-2-propynoyl) 苯甲醚的电促进环化合成 3-卤代黄酮类化合物

  摘要：

  用 N-氯代琥珀酰亚胺 (NCS) 或 N-溴代琥珀酰亚胺 (NBS) 处理 2-(1-aryl-3-propynoyl) 苯甲醚 1 以中等收率得到 3-卤代黄酮及其相关分子。

  DOI：

  10.1002/jccs.200400027

文献信息

• A phosphine-free, atom-efficient cross-coupling reaction of triorganoindiums with acyl chlorides catalyzed by immobilization of palladium(0) in MCM-41
  作者：Jiankang Miao、Bin Huang、Haiyi Liu、Mingzhong Cai

  DOI：10.1039/c7ra08355f

  日期：——

  first phosphine-free heterogeneous palladium(0)-catalyzed cross-coupling of triorganoindiums with acyl chlorides has been developed that proceeds smoothly in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable aryl ketones and α,β-acetylenic ketones with high atom-economy and high yield. This phosphine-free heterogeneous palladium(0) catalyst can be easily prepared

  已开发出首个无膦的异质钯（0）催化三有机铟与酰氯的交叉偶联反应，可在68°C的THF中顺利进行，并为合成各种有价值的芳基酮和α提供了通用而强大的工具，具有高原子经济性和高收率的β-炔酮。这种无膦的非均相钯（0）催化剂可以很容易地从市售试剂中制备，并可以通过简单过滤反应溶液进行回收，并至少进行10次连续试验而活性没有降低。我们的系统不仅避免使用膦配体，而且解决了钯催化剂回收和再利用的基本问题。
• Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization
  作者：Chengxiang Zhou、Anton V. Dubrovsky、Richard C. Larock

  DOI：10.1021/jo0523722

  日期：2006.2.1

  The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient

  ICl诱导的杂原子取代的炔酮的环化为各种3-碘色酮和类似物提供了一种简单，高效的方法。该过程在温和的条件下进行，可以耐受各种官能团，并且通常以高至优异的产率提供色酮。随后的钯催化转化使分子复杂性迅速增加，并方便地制备了多种功能取代的色酮，呋喃和多环化合物。碘硫代色素酮和碘喹啉酮也可通过类似的ICI诱导的环化反应制备。
• 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。
• 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。
• Copper-FreeSonogashira Coupling of Acid Chlorides with Terminal Alkynes in the Presence of a Reusable Palladium Catalyst: An Improved Synthesis of 3-Iodochromenones (=3-Iodo-4H-1-benzopyran-4-ones)
  作者：Pravin R. Likhar、M. S. Subhas、Moumita Roy、Sarabindu Roy、M. Lakshmi Kantam

  DOI：10.1002/hlca.200890032

  日期：2008.2

  Pd/C is used as an efficient catalyst for the copper-free Sonogashira coupling of acid chlorides and terminal alkynes to afford ynones in high yields (Tables 1 and 3). Cyclization of (2-methoxyaryl)-substituted ynones induced by I2/ammonium cerium(IV) nitrate (CAN) at room temperature gave 3-iodochromenones (=3-iodo-4H-1-benzopyran-4-ones) in excellent yield (Table 4).

  Pd / C用作酰基氯与末端炔烃的无铜Sonogashira偶联的有效催化剂，可高产率提供炔酮（表1和3）。在室温下，由I 2 /硝酸铈（IV）铵（CAN）诱导的（2-甲氧基芳基）取代的炔酮的环化反应得到极好的3-碘代色酮（= 3-碘代-4 H -1-苯并吡喃-4-酮）产量（表4）。