3-(3-硝基苯基)-2-丙烯醛 | 56578-39-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 3-(3-硝基苯基)-2-丙烯醛
• 英文名称: (E)-3-nitrocinnamaldehyde
• 英文别名: (E)-3-(3-nitrophenyl)acrylaldehyde；3-nitrocinnamaldehyde；m-nitrocinnamaldehyde；trans-3-nitrocinnamaldehyde；3-(3-Nitrophenyl)acrylaldehyde；(E)-3-(3-nitrophenyl)prop-2-enal
• CAS: 56578-39-3
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: JKTVNBZTQKQRSH-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  3-(3-硝基苯基)-2-丙烯醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-(3-硝基苯基)丙-2-烯-1-醇
  参考文献：
  名称：

  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

  摘要：

  CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 mu M, similar to 10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

  DOI：

  10.1021/acs.jmedchem.7b01300
• 作为产物：
  描述：

  1-碘-3-硝基苯 在 sodium tetrahydroborate 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 四丁基溴化铵 、 lithium acetate dihydrate 、 palladium diacetate 、 lithium chloride 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.17h， 生成 3-(3-硝基苯基)-2-丙烯醛
  参考文献：
  名称：

  醇的立体选择性有机催化氧化为烯类：制备多烯的同源方法

  摘要：

  开发了一种新型的通过氧化烯胺催化的有机催化氧化方法，该方法与由简单的饱和醇直接合成烯类具有优异的相容性。通过使用这种胺催化的IBX氧化，广泛的...

  DOI：

  10.1039/c5cc10093c

文献信息

• Efficient preparation of trans-α,β-unsaturated aldehydes from saturated aldehydes by oxidative enamine catalysis
  作者：ShiLei Zhang、HeXin Xie、AiGuo Song、DeYan Wu、Jin Zhu、SiHan Zhao、Jian Li、XinHong Yu、Wei Wang

  DOI：10.1007/s11426-011-4432-6

  日期：2011.12

  mild and highly efficient amine-catalyzed, IBX-mediated oxidation of aldehydes to (E) selective α,β-unsaturated aldehydes has been achieved in good yields. The process features a new oxidation of enamines to iminium ions in a catalytic fashion.

  已以良好的产率实现了温和且高效的胺催化，IBX介导的醛氧化为（E）选择性α，β-不饱和醛的氧化。该方法的特征在于以催化方式将烯胺新氧化为亚胺离子。
• NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
  作者：Anup Bhunia、Atanu Patra、Vedavati G. Puranik、Akkattu T. Biju

  DOI：10.1021/ol400562z

  日期：2013.4.5

  The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.

  用2'-羟基查耳酮对烯进行N杂环卡宾催化的环化反应，可得到环戊烷稠合的香豆素衍生物，具有极佳的非对映异构控制水平。该反应可耐受各种官能团。给出了25个示例，并提供了初步的机械研究。
• Preparation of γ,δ-unsaturated-β-ketoesters: Lewis acid-catalysed C H insertion of ethyl diazoacetate into α,β-unsaturated aldehydes
  作者：Hirenkumar Gandhi、Timothy P. O'Sullivan

  DOI：10.1016/j.tetlet.2017.07.095

  日期：2017.9

  synthesis of γ,δ-unsaturated-β-keto esters was achieved by the Lewis acid-catalysed direct CH insertion of an α-diazoester into various α,β-substituted-unsaturated aldehydes. CH insertion of ethyl diazoacetate into alkyl- and aryl-substituted α,β-unsaturated aldehydes was performed under mild conditions to afford the corresponding γ,δ-unsaturated-β-keto esters in moderate to high yields as a mixture

  γ，δ-不饱和-β-酮酸酯的合成是通过路易斯酸催化的α-重氮酯直接C H插入各种α，β-取代的不饱和醛中来实现的。在温和的条件下将重氮基乙酸乙酯C H插入烷基和芳基取代的α，β-不饱和醛中，以中等至高收率的酮/烯醇混合物形式提供相应的γ，δ-不饱和-β-酮酸酯互变异构体。
• A novel entry to xanthones by an intramolecular Diels-Alder reaction involving 2-(1,2-dichlorovinyloxy) aryl dienones
  作者：Katerina Otrubova、Anne E. Fitzgerald、Neelakandha S. Mani

  DOI：10.1016/j.tet.2018.08.007

  日期：2018.9

  of synthetic methods are described in the literature for the preparation of xanthones—a prominent class of tricyclic molecules that occur widely in nature. Majority of these reported methods involve linking the two aromatic rings and forming the central pyrone ring using a variety of classical and non-classical cyclization strategies. In a conceptually different approach, we describe here a new xanthone

  文献中描述了多种用于制备氧杂蒽酮的合成方法，所述杂合酮是自然界中广泛存在的一类重要的三环分子。这些报道的方法大多数涉及使用各种经典和非经典环化策略连接两个芳环并形成中心吡喃环。在概念上不同的方法中，我们在这里描述了一种新的x吨酮合成方法，其中吡喃酮和第二芳环均通过涉及2-（1,2-二氯乙烯基氧基）芳基二烯酮的分子内环加成反应在一个步骤中锻造而成。
• Synthesis and Anti-HIV-1 Activity of New Delavirdine Analogues Carrying Arylpyrrole Moieties.
  作者：Gérard Aimè PINNA、Giovanni LORIGA、Gabriele MURINEDDU、Giuseppe GRELLA、Massimo MURA、Laura VARGIU、Chiara MURGIONI、Paolo LA COLLA

  DOI：10.1248/cpb.49.1406

  日期：——

  In our search for novel anti-human immunodeficiency virus (HIV)-1 agents, 14 delavirdine analogues were synthesized and evaluated as potential anti-HIV-1 agents in cell-based assays. Compound 1Aa exhibited potent and selective anti-HIV-1 activity in acutely infected MT4 cells, with effective concentration (EC50) values in the submicromolar range.

  在我们寻找新型抗人免疫缺陷病毒（HIV）-1药物的过程中，合成了14种地拉维定类似物，并在基于细胞的测定中评估为潜在的抗HIV-1药物。化合物1Aa在急性感染的MT4细胞中表现出有效的和选择性的抗HIV-1活性，其有效浓度（EC50）值在亚微摩尔范围内。