methyl (5E)-2-oxo-6-phenylhexa-3,5-dienoate | 1228393-31-4

• 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: methyl (5E)-2-oxo-6-phenylhexa-3,5-dienoate
• CAS: 1228393-31-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: BIEGJZAIENLLGA-IIWBTEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-4-phenyl-1,3-butadiene 、 methyl (5E)-2-oxo-6-phenylhexa-3,5-dienoate 在 C₃₉H₆₀N₄O₄ 、 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-(5-methyl-3-((E)-styryl)-1,2,3,4-tetrahydro-[1,1′-biphenyl]-2-yl)-2-oxoacetate
  参考文献：
  名称：

  锌（II）催化的（E）-1-苯基二烯与β，γ-不饱和α-酮酸酯的不对称Diels-Alder反应

  摘要：

  通过使用稳定且容易获得的手性N，N'-二氧化物/ ，可以实现高度区域，非对映和对映选择性Diels-Alder反应与（E）-1-苯基二烯的β，γ-不饱和α-酮酸酯的反应锌（II）配合物作为催化剂。在温和的反应条件下，仅以良好至优异的收率获得了具有三个手性中心的相应环己烯的一种异构体。通过X射线衍射分析鉴定了产物和手性N，N'-二氧化物/锌（II）催化剂的构型。此外，提出了可能的催化模型来解释不对称感应的起源。

  DOI：

  10.1021/acs.joc.8b01771

文献信息

• Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines
  作者：Chunyin Zhu、Benwei Bi、Ya Ding、Te Zhang、Qiu-Yun Chen

  DOI：10.1016/j.tet.2015.10.040

  日期：2015.12

  An iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines in one step has been developed through the green reaction system of catalytic amounts of molecular iodine and amine in combination with oxygen. Various ketones and aldehydes were able to react with different chalcones and β, γ-unsaturated α-ketoesters through this reaction strategy. Synthetically

  通过催化量的分子碘和胺与氧结合的绿色反应体系，开发了一种碘催化好氧氧化形式[4 + 2]环化反应，该环化反应可一步一步构建多官能吡啶。通过该反应策略，各种酮和醛能够与不同的查耳酮和β，γ-不饱和的α-酮酸酯反应。综合这碘催化系统可以高效率地扩大规模。
• Highly enantioselective construction of carbazole derivatives via [4+2] cycloaddition of silyloxyvinylindoles and β,γ-unsaturated α-ketoesters
  作者：Xiaohu Zhao、Hongjiang Mei、Qian Xiong、Kai Fu、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c6cc05328a

  日期：——

  A highly efficient catalytic asymmetric [4+2] cycloaddition of silyloxyvinylindoles with [small beta],[gamma]-unsaturated [small alpha]-ketoesters has been accomplished by an avaliable chiral N,N[prime or minute]-dioxide/yttrium triflate complex. A widespread range of carbazole derivatives were obtained...

  通过可用的手性N，N [伯或分钟]-二氧化物/三氟甲磺酸钇可实现甲硅烷基氧乙烯基吲哚与β，γ-不饱和小α-酮酸酯的高效催化不对称[4 + 2]环加成反应复杂的。获得了广泛的咔唑衍生物。
• Highly enantioselective Michael addition of malonates to β,γ-unsaturated α-ketoesters catalyzed by chiral N,N′-dioxide-Yttrium(iii) complexes with convenient procedure
  作者：Lin Zhou、Lili Lin、Wentao Wang、Jie Ji、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c002208j

  日期：——

  Highly enantioselective Michael addition of malonates to beta,gamma-unsaturated alpha-ketoesters has been promoted by chiral N,N'-dioxide-Yttrium(iii) complexes, providing the corresponding products in excellent yields with 94-99% ee values.

  手性N，N'-二氧化物-钇（iii）配合物促进了丙二酸酯向β，γ-不饱和α-酮酸酯的高对映选择性迈克尔加成反应，从而提供了具有良好收率的相应产品，其ee值为94-99％。
• A mild and facile synthesis of polyfunctionalized pyridines: merging three-component cyclization and aerobic oxidation by amine/metal catalysts
  作者：Chunyin Zhu、Benwei Bi、Ya Ding、Te Zhang、Qiu-Yun Chen

  DOI：10.1039/c5ob00630a

  日期：——

  A mild and facile synthesis of polyfunctionalized pyridines from NH4OAc, β,γ-unsaturated α-ketoesters, and ketones/aldehydes has been reported through tandem three-component cyclization and aerobic oxidation using the combination of amine and metal catalysts. The synthetic value of the developed methodology was demonstrated by a gram-scale reaction and a wide range of substrates including naturally

  据报道，通过串联三组分环化和需氧氧化，结合胺和金属催化剂，可以由NH 4 OAc，β，γ-不饱和α-酮酸酯和酮/醛温和简便地合成多官能吡啶。克级反应和多种底物（包括天然存在的香茅醛）证明了所开发方法的综合价值。
• Visible-Light Photocatalytic Aerobic Annulation for the Green Synthesis of Pyrazoles
  作者：Ya Ding、Te Zhang、Qiu-Yun Chen、Chunyin Zhu

  DOI：10.1021/acs.orglett.6b01867

  日期：2016.9.2

  A selective and high yielding synthesis of polysubstituted pyrazoles through a VLPC (visible light photoredox catalysis)-promoted reaction of hydrazine with Michael acceptors is reported. The method employs very mild reaction conditions and uses air as the terminal oxidant, which makes the process environmentally benign. Different types of Michael acceptors with various substituents can undergo the

  报道了通过VLPC（可见光氧化还原催化）促进的肼与迈克尔受体的反应选择性和高产率地合成多取代的吡唑。该方法采用非常温和的反应条件，并使用空气作为末端氧化剂，这使该过程对环境无害。具有各种取代基的不同类型的迈克尔受体可以进行反应，以良好至优异的产率得到相应的吡唑。提出该反应是通过VLPC促进的肼氧化成重氮，然后将其加到迈克尔受体上，而不是肼与羰基的常规缩合反应。