(E)-3-(3-methoxy-2-nitrophenyl)acrylaldehyde | 262268-59-7

• 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: (E)-3-(3-methoxy-2-nitrophenyl)acrylaldehyde
• 英文别名: 3-(3-Methoxy-2-nitrophenyl)prop-2-enal；(E)-3-(3-methoxy-2-nitrophenyl)prop-2-enal
• CAS: 262268-59-7
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: LJPHCNNXLIRHHA-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-methoxy-2-nitrophenyl)acrylaldehyde 在 sodium hydroxide 、 bakers' yeast 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以10%的产率得到8-甲氧基喹啉氮氧化物
  参考文献：
  名称：

  Baker's yeast reduction of nitroarenes in NaOH media 5. Reductive cyclization of o-nitrocinnamaldehydes

  摘要：

  Reduction of 2-nitrocinnamaldehydes or 4-(2'-nitrophenyl)-3-buten-2-one by bakers' yeast has been found to be cyclized in NaOH media, resulting in the formation of quinolines via cyclized N-oxides. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00978-7

文献信息

• Cu(I)-/Base-Mediated Domino [5 + 3 + 1] Annulation for Highly π-Extended Carbazole Frameworks and DFT Mechanistic Insights
  作者：Tej Narayan Poudel、Sangita Karanjit、Hari Datta Khanal、Ramuel John Inductivo Tamargo、Yong Rok Lee

  DOI：10.1021/acs.orglett.8b02363

  日期：2018.9.21

  An efficient synthesis of highly π-extended carbazoles is described via an unexpected domino [5 + 3 + 1] annulation approach. The Cu(I)-/base-promoted reactions of 2-nitrocinnamaldehydes with benzyl cyanides provide diverse benzo[b]carbazoles. The reaction is proposed to proceed via a sequential Michael addition/intramolecular addition of an enol into a nitro group, 6π- electrocyclization, and the

  通过意外的多米诺骨牌[5 + 3 +1]环化方法描述了高效π-延伸的咔唑的高效合成方法。2-硝基肉桂醛与苄基氰化物的Cu（I）-/碱促进反应可提供各种苯并[ b ]咔唑。提出该反应是通过将烯醇依次加成到硝基中，分子内加成烯醇，进行6π-电环化和由密度泛函理论计算所支持的最终的氧化芳构化来进行的。一些合成的咔唑在Cu 2+离子的荧光传感中显示出显着的潜力。
• Mild Base-Promoted Indole Annulation-Oxidative Cross- Coupling of 2-Nitrocinnamaldehydes with β-Tetralones for 3-Naphthylindole and 3-Naphthylbenzo[<i>g</i> ]indole Fluorophores
  作者：Tej Narayan Poudel、Yong Rok Lee

  DOI：10.1002/adsc.201601327

  日期：2017.5.2

  (E)‐3‐(1‐nitronaphthalen‐2‐yl)acrylaldehyde with β‐tetralones for the construction of diverse 3‐naphthylindole and 3‐naphthylbenzo[g]indole fluorophores in moderate to good yields. This unique annulation reaction proceeds via the domino Michael addition/hemiacetalization/intramolecular addition of an enolate to a nitro group/decarbonylation/oxidative aromatization sequence under transition metal‐free conditions

  本文描述了2-硝基肉桂醛或（E）-3-（1-硝基萘-2-基）丙烯醛与β-四氢萘酮的无过渡金属吲哚环化-氧化交叉偶联，用于构建各种3-萘萘和3萘基苯并[ g ]吲哚荧光团的产率中等至良好。这种独特的环反应进行经由多米诺迈克尔加成/ hemiacetalization /分子内加成的烯醇化物与过渡不含金属的条件下硝基/脱羰/氧化芳构化序列，而无需使用外部还原剂和氧化剂的。通过评估合成的3-萘并吲哚和3-萘基苯并[ g]的光物理性质，也证明了该方案的合成效用。]吲哚衍生物。
• Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore
  作者：Jawad Alzeer、Jacques Chollet、Ingrid Heinze-Krauss、Christian Hubschwerlen、Hugues Matile、Robert G. Ridley

  DOI：10.1021/jm990002y

  日期：2000.2.1

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.
• KR101791790
  申请人：——

  公开号：——

  公开（公告）日：——