3-(4-methoxyphenyl)-3-phenylacrylaldehyde | 120555-67-1

• 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: 3-(4-methoxyphenyl)-3-phenylacrylaldehyde
• 英文别名: (Z)-3-(4-methoxyphenyl)-3-phenylacrylaldehyde；(Z)-3-(4-methoxyphenyl)-3-phenyl-2-propenal；(Z)-3-(4-methoxyphenyl)-3-phenylprop-2-enal
• CAS: 120555-67-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: ZNFSEHNKPWPRLU-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-methoxyphenyl)-3-phenylacrylaldehyde 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2E,4Z)-5-(4-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 4-nitrophenyl ester
  参考文献：
  名称：

  Pentadienyl carboxamide derivatives as antagonists of platelet activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,-E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxy-phenyl)-N- [1-methyl-4-(3-pyridinyl)butyl]- 2,4-pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4- (3-pyridinyl)butyl]-2,4-decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H- 1-(4-morpholinyl)-1-propanone (45).

  DOI：

  10.1021/jm00128a026
• 作为产物：
  描述：

  4-甲氧基二苯甲酮 在 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 3-(4-methoxyphenyl)-3-phenylacrylaldehyde 、 (E)-3-(4-methoxyphenyl)-3-phenylacrylaldehyde
  参考文献：
  名称：

  无金属和无酸的三氟甲基磺酸甲酯催化迈尔-舒斯特重排

  摘要：

  摘要 已经实现了从炔丙醇中无金属和无酸地合成有用的α，β-不饱和羰基化合物的新方法。这种Meyer-Schuster重排过程可通过三氟甲磺酸甲酯（20摩尔％）有效催化，制备出大范围的共轭E-烯醛和E-烯酮，收率通常高达90％。该反应过程在温和条件下（70°C）在空气中进行，反应时间短（1 h）。此外，在该转化过程中分离出了被溶剂2,2,2-三氟乙醇捕获的碳正离子中间体。 已经实现了从炔丙醇中无金属和无酸地合成有用的α，β-不饱和羰基化合物的新方法。这种Meyer-Schuster重排过程可通过三氟甲磺酸甲酯（20摩尔％）有效催化，制备出大范围的共轭E-烯醛和E-烯酮，收率通常高达90％。该反应过程在温和条件下（70°C）在空气中进行，反应时间短（1 h）。此外，在该转化过程中分离出了被溶剂2,2,2-三氟乙醇捕获的碳正离子中间体。

  DOI：

  10.1055/s-0036-1588800

文献信息

• [IrCp*(NCMe) ₂ (PPh ₂ Me)][PF ₆ ] ₂ as Catalyst for the Meyer–Schuster Rearrangement of Arylpropargylic Alcohols under Mild Conditions
  作者：María Talavera、Jorge Bravo、Luca Gonsalvi、Maurizio Peruzzini、Cristiano Zuccaccia、Sandra Bolaño

  DOI：10.1002/ejic.201402882

  日期：2014.12

  The novel iridium complex [IrCp*(NCMe)2(PPh2Me)][PF6]2 (I) efficiently catalyzed the Meyer–Schuster rearrangement of selected arylpropargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst. A mechanism involving a (hydroxy)alkenylcarbene intermediate is proposed.

  新型铱络合物 [IrCp*(NCMe)2(PPh2Me)][PF6]2 (I) 在温和条件下有效催化了所选芳炔丙醇的 Meyer-Schuster 重排为 α,β-不饱和醛，无需共聚反应。 -催化剂。提出了涉及（羟基）烯基卡宾中间体的机制。
• Copper-catalyzed formylation of alkenyl C–H bonds using BrCHCl₂ as a stoichiometric formylating reagent
  作者：Yan Bao、Gao-Yin Wang、Ya-Xuan Zhang、Kang-Jie Bian、Xi-Sheng Wang

  DOI：10.1039/c8sc00210j

  日期：——

  The first example of copper-catalyzed formylation of alkenyl C–H bonds with BrCHCl₂ as a stoichiometric formylating reagent for the facile synthesis of α,β-unsaturated aldehydes has been developed.

  以BrCHCl₂作为化学计量量的甲酰化试剂，首次实现了铜催化的烯丙基C-H键甲酰化反应，为简便合成α,β-不饱和醛提供了方法。

• Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity
  作者：Pronnoy G. Bangar、Priyanka R. Jawalkar、Swapnil R. Dumbre、Pallavi K. Raut、Dharmaraj J. Patil、Neethu Tv、Shana Sudhakaran、Suresh Iyer

  DOI：10.1080/00397911.2020.1811986

  日期：2020.12.16

  Abstract Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the

  摘要 在 TBABr/TBACl 存在下，芳基碘化物与 1,2-二取代芳基烯烃反应得到高产率的 Mizoroki-Heck 产物。膦配体用于调节反应性和立体选择性，用于 4-碘苯甲醚与肉桂醛的反应。tert-Bu3P.HBF4 的 E:Z 比最高，为 1:0.08。使用 PEG-200 和 PEG-400 作为溶剂可以激活芳基碘化物与各种 1,2-二取代芳基烯烃的反应。图形概要
• The Heck arylation of mono- and disubstituted olefins catalyzed by palladium supported on alumina-based oxides
  作者：Ewa Mieczyńska、Andrzej Gniewek、Iweta Pryjomska-Ray、Anna M. Trzeciak、Hanna Grabowska、Mirosław Zawadzki

  DOI：10.1016/j.apcata.2010.11.041

  日期：2011.2

  With the same catalysts, good results, up to 97% yield of ethyl β-phenylcinnamate (3), were also obtained in the coupling of bromobenzene with ethyl cinnamate. The three most active catalysts, Pd(0)/Al2O3, Pd(II)/Al2O3, and Pd(II)/Al2O3–Fe2O3, were applied in the Heck cross-coupling of cinnamates with different bromobenzene and iodobenzene derivatives, leading to β-arylcinnamate products. The highest

  通过醇盐溶胶-凝胶法（Al 2 O 3，Al 2 O 3 -ZrO 2，Al 2 O 3 -ZrO 2 -Eu 2制备）负载在氧化铝基混合氧化物上的含Pd（0）或Pd（II）的钯催化剂O 3，Al 2 O 3 –MgO，Al 2 O 3 –CeO 2，Al 2 O 3 –Fe 2 O 3）在DMF溶剂中对溴苯与丙烯酸丁酯的Heck偶联非常有效。在过量的溴苯存在下，4小时后形成肉桂酸丁酯（1）作为主要产物。使用相同的催化剂，在溴苯与肉桂酸乙酯的偶联中也获得了良好的结果，β-苯基肉桂酸乙酯（3）的产率高达97％。三种活性最高的催化剂Pd（0）/ Al 2 O 3，Pd（II）/ Al 2 O 3和Pd（II）/ Al 2 O 3 –Fe 2 O 3分别用于肉桂酸与不同的溴苯和碘苯衍生物的Heck交叉偶联，生成β-芳基肉桂酸酯产品。当碘代茴香醚和肉桂醛用作底物时，观察到最高产率。通过TEM测量证
• Palladium-Catalyzed Cascade Saegusa-Heck Reaction: Synthesis of β,β-Diarylacroleins from Arylpropanals and Aryl Iodides
  作者：Li Xiao、Yilin Zheng、Qiong Xie、Liming Shao

  DOI：10.1002/ejoc.201701025

  日期：2017.10.25

  An efficient Pd-catalyzed Saegusa–Heck cascade protocol for the preparation of synthetically useful β,β-diarylacroleins in moderate to high yields (30–83 %) from arylpropanals and aryl iodides is developed.

  开发了一种有效的Pd催化的Saegusa-Heck级联方案，用于从芳族丙醛和碘代芳烃中到高产率（30-83％）制备合成有用的β，β-二芳基丙烯醛。