(E)-2-(4'-methoxyphenyl)-1-nitro-1-phenylethene | 37629-90-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4'-methoxyphenyl)-1-nitro-1-phenylethene
• 英文别名: 1-methoxy-4-[(E)-2-nitro-2-phenylvinyl]benzene；(E)-4'-methoxy-α-nitrostilbene；α'-nitro-4-methoxy-cis-stilbene；α'-Nitro-4-methoxy-cis-stilben；1-Nitro-1-phenyl-2-(p-anisyl)-ethylen；4'-Methoxy-α-nitrostilben(E)；1-Methoxy-4-[(1E)-2-nitro-2-phenylethenyl]benzene；1-methoxy-4-[(E)-2-nitro-2-phenylethenyl]benzene
• CAS: 37629-90-6
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: FQZGLHHMTHWCKD-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4'-methoxyphenyl)-1-nitro-1-phenylethene 以 甲醇 为溶剂， 生成 4'-Methoxy-α-nitrostilben(Z)
  参考文献：
  名称：

  Blake,K.W.; Jaques,B., Journal of the Chemical Society. Perkin transactions II, 1973, p. 1660 - 1663

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-Methoxy-α-nitrostilben(Z) 在 乙醇 作用下， 生成 (E)-2-(4'-methoxyphenyl)-1-nitro-1-phenylethene
  参考文献：
  名称：

  Fluerscheim; Holmes, Journal of the Chemical Society, 1932, p. 1458,1463

  摘要：

  DOI：

文献信息

• Synthesis of Unsymmetrical 3,4-Diaryl-3-pyrrolin-2-ones Utilizing Pyrrole Weinreb Amides
  作者：Jessica G. Greger、Sarah J. P. Yoon-Miller、Nathan R. Bechtold、Scott A. Flewelling、Jacob P. MacDonald、Catherine R. Downey、Eric A. Cohen、Erin T. Pelkey

  DOI：10.1021/jo2013516

  日期：2011.10.21

  A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2)

  从 1,2-二芳基-1-硝基乙烯以吡咯-2-甲酰胺（吡咯 Weinreb 酰胺）作为关键的关键三步实现了不对称 3,4-二芳基-3-吡咯啉-2-酮的区域控制合成中间体。研究了两种不同的制备所需硝基烯烃的方法：（1）芳基硝基甲烷和芳基亚胺之间的改性亨利反应；(2) 2-芳基-1-溴-1-硝基乙烯与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应。在芳基硝基甲烷的制备过程中遇到了一些困难，因此探索了一种被证明更有用的交叉偶联策略。1,2-二芳基-1-硝基乙烯与N-甲氧基-N之间的Barton-Zard吡咯环缩合反应-甲基-2-异氰基乙酰胺得到相应的吡咯 Weinreb 酰胺，然后分两步将其转化为所需的 3-吡咯啉-2-酮。总体而言，该方法允许构建 3,4-二芳基-3-吡咯啉-2-酮，并完全控制内酰胺羰基的取代基区域。通过制备八种不对称和对称的 3,4-diaryl-3-pyrrolin-2-ones，包括选择性
• Reductive Denitrogenation of Six‐membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System
  作者：Evgeny V. Pospelov、Alexander V. Zhirov、Baglan Kamidolla、Alexey Yu. Sukhorukov

  DOI：10.1002/adsc.202300573

  日期：2023.9.5

  A protocol for the synthesis of 2,3-dihydrofurans by reductive denitrogenation/ring contraction of 6-membered cyclic nitronates was developed. The process utilizes cheap Raney® nickel both as catalyst and stoichiometric agent without the need for high-pressure equipment. The products are formed in high purity and column chromatography is often not required. Studies on the substrate scope, functional

  开发了通过六元环状硝基化合物的还原脱氮/环收缩合成 2,3-二氢呋喃的方案。该工艺利用廉价的 Raney® 镍作为催化剂和化学计量试剂，无需高压设备。产品以高纯度形成，通常不需要柱色谱法。对底物范围、官能团耐受性和机制进行了研究。所开发的方法提供了一种直接的两步从硝基苯乙烯和烯烃制备密集取代的2,3-二氢呋喃的方法。
• Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]‐Cycloaddition/Reductive Ring Contraction Strategy
  作者：Evgeny V. Pospelov、Alexander V. Zhirov、Baglan Kamidolla、Alexey Yu. Sukhorukov

  DOI：10.1002/ejoc.202400627

  日期：2024.8.12

  of nitroalkenes with enol ethers followed by reductive ring contraction of the resulting cyclic nitronates provides a new access to polysubstituted NH pyrroles. Unlike conventional synthetic routes (Barton-Zard, Knorr, Hantzsch, Van Leusen pyrrole syntheses), this strategy affords NH pyrroles that do not necessarily contain a EWG group in the ring.

  硝基烯烃与烯醇醚的[4+2]-环加成，随后所得环状硝基化合物的还原环收缩提供了获得多取代NH吡咯的新途径。与传统的合成路线（Barton-Zard、Knorr、Hantzsch、Van Leusen 吡咯合成）不同，该策略提供的 NH 吡咯在环中不一定包含 EWG 基团。
• Dore,J.-C. et al., Chimica Therapeutica, 1971, vol. 6, p. 167 - 185
  作者：Dore,J.-C. et al.

  DOI：——

  日期：——
• Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
  作者：Madhu Ganesh、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2007.09.012

  日期：2007.11

  (Z)-alpha-Bromo-beta-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)(4) as catalyst to afford (E)-alpha,beta-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of alpha-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful alpha,beta-disubstituted nitroethylenes. (c) 2007 Elsevier Ltd. All rights reserved.