4-cyanocinnamaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 4-cyanocinnamaldehyde
• 英文别名: 4-(3-oxoprop-1-en-1-yl)benzonitrile；p-Cyanocinnamaldehyde；4-(3-oxoprop-1-enyl)benzonitrile
• 化学式: C₁₀H₇NO
• 分子量: 157.172
• InChiKey: RYMCARXOHQPZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-cyanocinnamaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 N-溴代丁二酰亚胺(NBS) 、 苯甲酸 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 (S)-methyl 3-(4-cyanophenyl)-4-nitrobutanoate
  参考文献：
  名称：

  有机催化一锅法不对称合成γ-硝基酯

  摘要：

  提出了通过对α，β-不饱和醛的一锅式不对称迈克尔加成/氧化酯化反应对γ-硝基酯的对映选择性合成。该程序基于将对映选择性有机催化硝基烷烃加成与基于N-溴琥珀酰亚胺的氧化合并。以良好的产率和对映选择性获得γ-硝基酯，并且该方法为旋光性γ-氨基酯，2-哌啶酮和2-吡咯烷酮提供了有吸引力的入口。

  DOI：

  10.1021/ol3002514
• 作为产物：
  描述：

  4-(prop-1-en-1-yl)benzonitrile 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73%的产率得到4-cyanocinnamaldehyde
  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。
• Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3‐Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
  作者：Marvin Stephan、Jesco Panther、Fabio Wilbert、Pauline Ozog、Thomas J. J. Müller

  DOI：10.1002/ejoc.202000066

  日期：2020.4.16

  The Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using CataCXium® Ptb as a ligand, NaHCO3 as a base, and nBu4NCl provides an efficient access to 3‐(hetero)aryl propenals/propenones, which are directly employed in consecutive multicomponent syntheses of pyrazoles in a one‐pot fashion.

  使用CataCXium®Ptb作为配体，NaHCO 3作为碱和n Bu 4 NCl进行（杂）芳基溴化物和丙烯醛或乙烯基酮的Heck反应，可以有效地获得3-（杂）芳基丙烯/丙烯酮。以单罐方式直接用于吡唑的连续多组分合成中。
• Metal-free and highly regioselective synthesis of N-heteroaryl substituted pyrazoles from α,β-unsaturated N-tosylhydrazones and heteroaryl chlorides
  作者：Lin Zeng、Xiao-Qiang Guo、Zai-Jun Yang、Ya Gan、Lian-Mei Chen、Tai-Ran Kang

  DOI：10.1016/j.tetlet.2019.07.034

  日期：2019.8

  β-unsaturated N-tosylhydrazones with N-heteroaryl chlorides was developed for the synthesis of N-heteroaryl pyrazole derivatives. This one-pot reaction provided bi(heteroaryl) derivatives in good to excellent yields and with excellent regioselectivity. The procedure is operationally simple and applicable to large-scale synthesis.

  级联环化/亲核芳香取代（S Ñ AR）α的反应，β不饱和Ñ与-tosylhydrazones ñ -杂芳基氯化物被用于合成开发Ñ -杂芳基吡唑衍生物。该一锅法反应以良好的至优异的产率和优异的区域选择性提供了双（杂芳基）衍生物。该程序操作简单，适用于大规模合成。
• Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides
  作者：Marta Meazza、Maria Ashe、Hun Yi Shin、Hye Sung Yang、Andrea Mazzanti、Jung Woon Yang、Ramon Rios

  DOI：10.1021/acs.joc.5b02801

  日期：2016.5.6

  Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.

  在本文中，我们描述了使用苄基氯作为双功能（亲核和亲电）试剂对烯类化合物进行首次对映选择性环丙烷化。通过手性仲胺简单地催化该反应，以高收率和中等至优异的立体选择性提供甲酰基环丙烷衍生物。
• Highly Regio- and Stereodivergent Access to 1,2-Amino Alcohols or 1,4-Fluoro Alcohols by NHC-Catalyzed Ring Opening of Epoxy enals
  作者：Si Bei Poh、Jun-Yang Ong、Shenci Lu、Yu Zhao

  DOI：10.1002/anie.201709823

  日期：2018.2.5

  Described is an unprecedented NHC‐catalyzed (NHC=N‐heterocyclic carbene), stereoselective ring opening of epoxy and cyclopropyl enals to deliver valuable compounds bearing multiple stereocenters. A straightforward three‐step procedure involving two catalytic enantioselective transformations has been developed and leads to a regio‐ and stereodivergent synthesis of either 1,2‐amino alcohols/diamines

  描述了前所未有的NHC催化（NHC = N-杂环卡宾），环氧和环丙基烯醛的立体选择性开环，以提供带有多个立体中心的有价值的化合物。已经开发了一种简单的三步方法，涉及两个催化对映选择性转化，并导致区域和立体发散合成具有出色的非对映和对映纯度的1,2-氨基醇/二胺或1,4-氟醇。