4-(3-oxo-1-propen-1-yl)benzoic acid methyl ester | 73166-52-6

• 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: 4-(3-oxo-1-propen-1-yl)benzoic acid methyl ester
• 英文别名: methyl 4-(3-oxoprop-1-en-1-yl)benzoate；methyl (E)-4-(3-oxoprop-1-en-1-yl)benzoate；4-methoxycarbonyl-cinnamaldehyde；methyl 4-(3-oxopropenyl)benzoate；Methyl 4-(3-[13C]Oxo-1-propenyl)benzoate；methyl 4-(3-oxoprop-1-enyl)benzoate
• CAS: 73166-52-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: DGFSQBWTYWEVET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-oxo-1-propen-1-yl)benzoic acid methyl ester 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 methyl (E)-4-(3-hydroxyprop-1-en-1-yl)benzoate
  参考文献：
  名称：

  通过镍亲核硅与烯丙醇的镍催化交叉偶联合成烯丙基硅烷。

  摘要：

  进行了NiCl2（PMe3）2催化的烯丙醇与甲硅烷基锌试剂（包括PhMe2SiZnCl，Ph2MeSiZnCl和Ph3SiZnCl）的反应，以高收率获得了烯丙基硅烷。芳基和杂芳基取代的烯丙醇，（E）-3-芳基丙-2-烯-1-醇，1-芳基丙-2-烯-1-醇和（E）-1-苯基戊-1-醇en-3-ol可用于转化。容许一定范围的官能团以及杂芳基。当使用1-或3-芳基取代的烯丙醇作为底物时，反应表现出高的区域选择性和E / Z-选择性。手性烯丙醇（S，E）-1-苯基戊-1-烯-3-醇的反应生成构型反转产物（R，E）-二甲基（苯基）（1-苯基戊-1-烯-3） -基）硅烷。

  DOI：

  10.1021/acs.orglett.9b02946
• 作为产物：
  描述：

  methyl 4-(prop-1-en-1-yl)benzoate 在 叔丁基过氧化氢 、 Ru(TPTTP)Cl₂ 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以74%的产率得到4-(3-oxo-1-propen-1-yl)benzoic acid methyl ester
  参考文献：
  名称：

  Evolution of physical and photocatalytic properties of new Zn(II) and Ru(II) complexes

  摘要：

  Synthesis of Zn(II) and Ru(II) complexes were reported by using N-4-macrocyclic Schiff base ligands under solvothermal conditions. The newly synthesized Zn(II) and Ru(II) complexes have been characterized by various physico-chemical techniques such as elemental analysis, molar conductance, HRMS, TGA, FESEM, UV-Vis, FT-IR, H-1 NMR, and cyclic voltammetry. By using molar conductance studies, the complexes are formulated as [Zn(TPTTP)]Cl-2 and [Ru(TPTTP)Cl-2]. C-H bond activation of an sp a group of methylstyrenes (converted into cinnamaldehydes) and C-H bond activation of the sp(2) bond of polycyclic aromatic hydrocarbons through photooxidation was examined in the presence of Zn(II) and Ru(II) complexes. Reusable activity studies and photostability of catalyst are investigated by using UV-Vis spectra. Based on the results, higher catalytic activity of [Ru(TPTTP)Cl-2] complex than [Zn(TPTTP)]Cl-2 complex in both C-H bond activation and photooxidation of aromatic hydrocarbons has been reported. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.05.065

文献信息

• Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals
  作者：Dehai Liu、Jie Huang、Zhenqian Fu、Wei Huang

  DOI：10.1039/c9gc00064j

  日期：——

  The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope

  通过2-甲基-吲哚-3-甲醛与LiCl / DBU促进的烯醛在一次操作中的反应即可直接快速构建咔唑。这种温和而绿色的反应通过[4 + 2]环加成/脱水/氧化芳构化级联进行，从而生成咔唑，收率好至极佳。该反应具有温和的反应条件，广泛的底物范围和出色的官能团耐受性，使用O 2（1 atm）作为唯一氧化剂，并提供H 2 O作为唯一的副产物。更重要的是，仅需一步就可以从得到的咔唑生成80％收率的重要的生物活性化合物4-氟喹咔唑。
• Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
  作者：Qiao Chen、Tingshun Zhu、Pankaj Kumar Majhi、Chengli Mou、Huifang Chai、Jingjie Zhang、Shitian Zhuo、Yonggui Robin Chi

  DOI：10.1039/c8sc03480j

  日期：——

  An N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes allows for quick access to optical pure benzimidazole-fused lactams.

  通过N-杂环卡宾催化的炔醛和二(杂)芳基甲烷的直接氧化偶联，可以快速获得光学纯的苯并咪唑-融合内酰胺。

• Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
  作者：Martin Kamlar、August Runemark、Ivana Císařová、Henrik Sundén

  DOI：10.1021/acs.orglett.0c03020

  日期：2020.11.6

  polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization.

  在这里，我们提出了氧代三苯基己酸酯的多环化。多环化受电子效应控制，并且已经建立了三个主要合成路径，导致具有多达五个立体中心的立体化学复杂的三环框架。该方法与一系列官能团兼容，允许在环化后引入药效基团元件。
• Molecular iodine catalysed domino cyclization in aqueous medium: a simple and efficient synthetic route to 1,4-dihydropyridazines
  作者：I. R. Siddiqui、Rahila Rahila、Pragati Rai、Hozeyfa Sagir、Malik A. Waseem

  DOI：10.1039/c5ra05370f

  日期：——

  An efficient protocol has been developed for the synthesis of dihydropyridazines using molecular iodine as green catalyst.

  已开发出一种高效的协议，使用分子碘作为绿色催化剂合成二氢吡啶。
• Synthesis of 3-Trifluoromethyl-1,4-dihydropyridazines by the PTSA-Catalyzed Reaction of α,β-Unsaturated Aldehydes with (E)-1-Phenyl-2-(2,2,2-trifluoroethylidene)
  作者：Yongming Wu、Haibo Xie、Jiangtao Zhu、Zixian Chen、Shan Li

  DOI：10.1055/s-0031-1290608

  日期：2012.4

  A facile and efficient method for the synthesis 3-trifluoromethyl-1,4-dihydropyridazine from a variety of readily available α,β-unsaturated aldehyde and (E)-1-phenyl-2-(2,2,2-trifluoroethylidene)hydrazine was developed. The reaction proceeded under mild conditions and gave the expected 1,4-dihydropyridazine products in moderate to high yields.

  开发了一种简便且高效的方法，利用多种易得的不饱和醛和(E)-1-苯基-2-(2,2,2-三氟亚乙基)肼合成3-三氟甲基-1,4-二氢吡啶嗪。该反应在温和条件下进行，并以中等至高产率得到预期的1,4-二氢吡啶嗪产物。