1-乙氧基-4-[(E)-2-硝基乙烯基]苯 | 6946-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-乙氧基-4-[(E)-2-硝基乙烯基]苯
• 英文名称: 2-(4'-ethoxyphenyl)-1-nitroethene
• 英文别名: 1-ethoxy-4-(2-nitrovinyl)benzene；α-Nitro-4-ethoxy-styrol；1-Ethoxy-4-(2-nitroethenyl)benzene
• CAS: 6946-30-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: LCRQRRBRHHLEHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  吲哚 、 1-乙氧基-4-[(E)-2-硝基乙烯基]苯 在 六氟异丙醇 作用下， 反应 2.0h， 以96%的产率得到3-(1-(4-ethoxyphenyl)-2-nitroethyl)-1H-indole
  参考文献：
  名称：

  以氟化醇作为氢键供体和溶剂的弗里德尔-克来福特烷基化反应†

  摘要：

  据报道，在 HFIP 中吲哚和富电子芳烃与 β-硝基烯烃发生有效且清洁的 FC 烷基化。在温和条件下以优异的产率快速形成所需产物，无需任何额外的催化剂或试剂。此外，该方法可应用于生物活性色胺衍生物的一锅合成。

  DOI：

  10.1039/c8ra01397g
• 作为产物：
  描述：

  硝基甲烷 、 4-乙氧基苯甲醛 在 环己胺 、 溶剂黄146 作用下， 反应 24.0h， 以92%的产率得到1-乙氧基-4-[(E)-2-硝基乙烯基]苯
  参考文献：
  名称：

  2-Arylthiomorpholine derivatives as potent and selective monoamine oxidase B inhibitors

  摘要：

  2-Arylthiomorpholine and 2-arylthiomorpholin-5-one derivatives, designed as rigid and/or non-basic phenylethylamine analogues, were evaluated as rat and human monoamine oxidase inhibitors. Molecular docking provided insight into the binding mode of these inhibitors and rationalized their different potencies. Making the phenylethylamine scaffold rigid by. xing the amine chain in an extended six-membered ring conformation increased MAO-B (but not MAO-A) inhibitory activity relative to the more flexible alpha-methylated derivative. The presence of a basic nitrogen atom is not a prerequisite in either MAO-A or MAO-B. The best K-i values were in the 10(8) M range, with selectivities towards human MAO-B exceeding 2000-fold. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.029

文献信息

• Water-soluble (salicyladimine)₂Cu complex as an efficient and renewable catalyst for Michael addition of indoles to nitroolefins in water
  作者：Haojie Jiang、Jie Zhang、Jianwei Xie、Ping Liu、Mei Xue

  DOI：10.1080/00397911.2016.1258478

  日期：2017.2.1

  ABSTRACT An efficient and environmentally friendly protocol has been demonstrated for water-soluble (salicyladimine)2Cu complex-catalyzed Michael addition of indoles to nitroolefins in water at 30 °C. A variety of substituted indoles and β-nitrostyrenes could be worked well to provide the title products in 81–97% yields. Moreover, the catalyst can be reused directly at least for four times without

  摘要 在 30 °C 下，水溶性（水杨酸二亚胺）2Cu 络合物催化吲哚与硝基烯烃迈克尔加成反应是一种高效且环保的方案。各种取代的吲哚和 β-硝基苯乙烯可以很好地工作，以 81-97% 的产率提供标题产品。此外，催化剂可以直接重复使用至少四次，而不会显着降低活性。图形概要
• Metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones
  作者：Alexander V. Aksenov、Alexander N. Smirnov、Nicolai A. Aksenov、Inna V. Aksenova、Jonathon P. Matheny、Michael Rubin

  DOI：10.1039/c4ra14406f

  日期：——

  3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation

  3-取代的2-喹诺酮是通过2-硝基烯烃与2-取代的吲哚在多磷酸中的新型无金属环转移反应获得的。这种酸介导的级联转化通过ANRORC（亲核试剂的添加，开环和闭环）机理进行操作，可以与Fisher吲哚合成结合使用，以提供一种实用的三组分杂环化方法从芳基肼，2-硝基烯烃和苯乙酮。还证明了该化学方法的另一种选择，该方法采用了富电子芳烃和戊烯与1-（2-吲哚基）-2-硝基烯烃的烷基化反应。
• Nitroalkenes as surrogates for cyanomethylium species in a one-pot synthesis of non-symmetric diarylacetonitriles
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Zarema V. Dzhandigova、Dmitrii A. Aksenov、Michael Rubin

  DOI：10.1039/c5ra20953f

  日期：——

  Nitroalkenes were used as synthetic equivalents of the cyanomethylium cation in a modular, one-pot synthesis of 2-(3-indolyl)acetonitriles and 2,2-diarylacetonitriles involving electrophilic functionalization of aromatic and heteroaromatic C–H bond.

  硝基烯烃被用作氰基甲基阳离子的合成等价物，用于2-（3-吲哚基）乙腈和2,2-二芳基乙腈的模块式一锅合成，涉及芳族和杂芳族CH键的亲电子官能化。
• Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones
  作者：Alexander V. Aksenov、Alexander N. Smirnov、Nicolai A. Aksenov、Inna V. Aksenova、Liliya V. Frolova、Alexander Kornienko、Igor V. Magedov、Michael Rubin

  DOI：10.1039/c3cc45696j

  日期：——

  3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

  3-取代的2-喹啉是通过2-取代吲哚与2-硝基烯烃在聚磷酸中进行的新型无金属跨环反应获得的。该反应可以与费舍尔吲哚合成联用，提供了一种实用的三组分杂环闭环方法，将芳基肼、2-硝基烯烃和乙酰苯one转化为2-喹啉。
• An efficient synthesis of (3-indolyl)acetonitriles by reduction of hydroxamic acids
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Zarema V. Dzhandigova、Inna V. Aksenova、Leonid G. Voskressensky、Alexander N. Smirnov、Michael A. Rubin

  DOI：10.1007/s10593-016-1881-z

  日期：2016.5

  A new, highly efficient method was developed for the synthesis of (3-indolyl)acetonitriles by reduction of readily available (3-indolyl)hydroxamic acids with phosphorus trichloride. The nitriles obtained according to this method are of significant interest for structure-activity studies of potential anticancer agents.

  通过用三氯化磷还原易得的（3-吲哚基）异羟肟酸，开发了一种新的高效方法来合成（3-吲哚基）乙腈。根据该方法获得的腈对于潜在抗癌剂的结构活性研究具有重大意义。