(Z)-1-(4-methoxyphenyl)-2,3-diphenylprop-2-en-1-one | 94348-27-3

• 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: (Z)-1-(4-methoxyphenyl)-2,3-diphenylprop-2-en-1-one
• 英文别名: (Z)-1-(p-methoxyphenyl)-2,3-diphenyl-2-propen-1-one；(Z)-1-(p-methoxyphenyl)-2,3-diphenylprop-2-en-1-one；(Z)-2,3-diphenyl-1-(4-methoxyphenyl)-2-propen-1-one；1-(4-Methoxyphenyl)2,3-diphenyl-prop-2-en-1-one
• CAS: 94348-27-3
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: UIDIQFLDNBTXLZ-PGMHBOJBSA-N

物化性质

• 熔点：
  88.7-89.2 °C
• 沸点：
  476.7±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基-2-苯基苯乙酮 、 苯甲醛 以38%的产率得到
  参考文献：
  名称：

  KUMAR, SURAT;RASTOGI, SHRI NIVAS, INDIAN J. CHEM., 26,(1987) N 10, 968-971

  摘要：

  DOI：

文献信息

• Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction
  作者：Levent Artok、Melih Kuş、Özge Aksın-Artok、Fatma Nurcan Dege、Fatma Yelda Özkılınç

  DOI：10.1016/j.tet.2009.09.044

  日期：2009.11

  Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.

  炔烃在铑（I）催化剂存在下，在CO气氛下与有机硼反应，主要生成5-芳基-2（5 H）-呋喃酮，α，β-不饱和酮和茚满酮。产物的选择性可以通过改变反应条件来调节。
• Ruthenium-Catalyzed Intermolecular Hydroacylation of Internal Alkynes: The Use of Ceria-Supported Catalyst Facilitates the Catalyst Recycling
  作者：Hiroki Miura、Kenji Wada、Saburo Hosokawa、Masashi Inoue

  DOI：10.1002/chem.201203530

  日期：2013.1.14

  Versatile and practical: Intermolecular hydroacylation of internal alkynes takes place in the presence of Ru catalysts together with HCO2Na and Xantphos to give the corresponding conjugated enones. Aromatic aldehydes with or without coordinating groups could be used in the present catalytic system. The solid Ru/CeO2 catalysts can be recycled for several times without significant decreases in yield

  多功能和实用：内部炔烃的分子间加氢酰化反应在Ru催化剂与HCO 2 Na和Xantphos共同存在下进行，从而得到相应的共轭烯酮。具有或不具有配位基团的芳族醛可以用于本催化体系中。固体Ru / CeO 2催化剂可以循环使用几次，而收率没有明显降低（参见方案）。
• Rhodium(I)-Catalyzed Carbonylative Arylation of Alkynes with Arylboronic Acids Using Formaldehyde as a Carbonyl Source
  作者：Tsumoru Morimoto、Chuang Wang、Hiroyuki Kanashiro、Hiroki Tanimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi、Levent Artok

  DOI：10.1055/s-0033-1341046

  日期：——

  The rhodium(I)-catalyzed reaction of alkynes with arylboronic acids in the presence of formaldehyde resulted in a carbon monoxide gas-free carbonylative arylation to yield α,β-enones. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis, which catalyze the abstraction of a carbonyl moiety from formaldehyde (decarbonylation) and its

  在甲醛存在下，炔烃与芳基硼酸的铑 (I) 催化反应导致无一氧化碳气体的羰基化芳基化反应生成 α,β-烯酮。高效催化需要同时加载连接膦和不含膦的铑 (I) 配合物，分别催化从甲醛中提取羰基部分（脱羰），然后将其引入底物（羰基化）。
• Structure-activity relationship of estrogens: receptor affinity and estrogen antagonist activity of certain (E)- and (2)-1,2,3-triaryl-2-propen-2-ones
  作者：Shubhra Mittal、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00382a019

  日期：1985.4

  (E)- and (Z)-1,2,3-triphenyl-2-propen-1-ones and some of their phenolic and alkoxy analogues, substituted at the para position in one or more of the aromatic rings, were synthesized and assigned geometry on the basis of their spectroscopic data. The structure-activity relationship of the triarylpropenones was studied from the point of view of their estrogen receptor affinity and estrogen agonist and antagonist activities. (E)- as well as (Z)-propenones were found to compete with estradiol for binding with the mouse uterine cytosol receptors, with phenolic analogues usually more potent than the unsubstituted as well as alkoxypropenones. The (E)-propenones, which have now emerged as a new group of estrogen receptor ligands, were found to differ from Z isomers quite markedly in their binding specificities. The uterotrophic and antiuterotrophic assays in immature mice revealed that while some of the compounds were marginally estrogenic, nearly all the isomeric propenones were antiestrogenic to a varying degree.

  (E)-和(Z)-1,2,3-三苯甲丙二烯酮及其酚类和醚类的类物在芳香环的para位被取代的情况下被合成了，这些化合物的立体结构是基于它们的光谱数据进行判断的。从雌激素受体亲和力以及雌激素亲和力的协同作用和拮抗作用的层面，探讨了丙三环酮的结构活性关系。无论是(E)-还是(Z)-的丙烯酮都与小鼠子宫细胞受体发生了竞争性的结合，酚类的类物通常比未取代的结构和醚类的丙烯酮有更强的亲和力。可以与雌激素结合的丙烯酮的身影作为新的雌激素受体配体逐渐浮现，但它们与(Z)-同分异构体在结合特异性方面有很大的不同。生胎性以及抑生胎性在幼鼠中的测试显示，虽然有些化合物具有微弱的雌激素性质，但几乎所有的同分异构体丙烯酮都具有一定程度的抑生胎性。
• Stereo-controlled <i>anti</i>-hydromagnesiation of aryl alkynes by magnesium hydrides
  作者：Bin Wang、Derek Yiren Ong、Yihang Li、Jia Hao Pang、Kohei Watanabe、Ryo Takita、Shunsuke Chiba

  DOI：10.1039/d0sc01773f

  日期：——

  anti-hydromagnesiation of aryl alkynes was established using 1 : 1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental

  在不借助任何过渡金属催化剂的情况下，使用氢化钠（NaH）和碘化镁（MgI 2）的1：1摩尔结合物建立了芳基炔烃抗氢放大的简明方案。所得的烯基镁中间体可以被一系列亲电试剂捕获，从而提供了对立体化学上定义明确的官能化烯烃的便捷通道。通过实验和理论方法进行的机理研究表明，从氢化镁（MgH 2）中添加极性氢化物是该过程的原因。