ethyl (2Z)-3-(4-nitrophenyl)prop-2-enoate | 51507-21-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-3-(4-nitrophenyl)prop-2-enoate
• 英文别名: ethyl (Z)-3-(4-nitrophenyl)acrylate；(Z)-ethyl 3-(4-nitrophenyl)acrylate；ethyl 3-(4-nitrophenyl)acrylate；cis-p-Nitrozimtsaeure-ethylester；ethyl (Z)-3-(4-nitrophenyl)prop-2-enoate
• CAS: 51507-21-2
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: PFBQVGXIMLXCQB-YVMONPNESA-N

物化性质

• 熔点：
  86-87 °C(Solv: ethanol (64-17-5))
• 沸点：
  326.6±17.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  ethyl (2Z)-3-(4-nitrophenyl)prop-2-enoate 在 palladium-on-activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 以86%的产率得到3-(4-氨基苯基)丙酸乙酯
  参考文献：
  名称：

  Methods of using .alpha.-phosphonosulfonate squalene synthetase

  摘要：

  提供了抑制酶角鲨烯合酶并从而抑制胆固醇生物合成的.alpha.-磷酸磺酸酯化合物。这些化合物的化学式为##STR1##其中R.sup.2为OR.sup.5或R.sup.5a；R.sup.3和R.sup.5独立地为H、烷基、芳基烷基、芳基或环烷基；R.sup.5a为H、烷基、芳基烷基或芳基；R.sup.4为H、烷基、芳基、芳基烷基或环烷基；Z为H、卤素、低烷基或低烯基；R.sup.1为至少含有7个碳原子的疏水基团，为烷基、烯基、炔基、混合烯基-炔基、芳基、芳基烷基、环烷基、环烷基烷基、杂环芳基、杂环芳基烷基、环杂环烷基、环杂环烷基烷基；如上所述；包括磷酸(亚磷酸)和/或磺酸的药用可接受盐和/或前药酯。

  公开号：

  US05470845A1
• 作为产物：
  描述：

  对硝基苯甲醛 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以70%的产率得到ethyl (2Z)-3-(4-nitrophenyl)prop-2-enoate
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• OMS-2 for Aerobic, Catalytic, One-pot Alcohol Oxidation-Wittig Reactions: Efficient Access to α,β-Unsaturated Esters
  作者：Jagadeswara R. Kona、Cecil K. King'ondu、Amy R. Howell、Steven L. Suib

  DOI：10.1002/cctc.201300942

  日期：2014.3

  found to be highly active for obtaining α,β‐unsaturated esters (up to 95 % yield and with high diastereoselectivities) from a variety of benzyl, heteroaryl, allyl and alkyl alcohols via one‐pot alcohol oxidation‐Wittig reaction. The transformation utilizes air as the stoichiometric oxidant, and the inexpensive catalyst can be recovered and reused.

  具有明确孔隙的氧化锰八面体分子筛（OMS）材料由于其令人着迷的化学和物理特性而被广泛研究了二十多年。OMS-2是锰的一种合成的三聚氰胺锰氧化物，是通过改进的回流方法合成的，被发现对从各种苄基中获得α，β-不饱和酯（产率高达95％且具有高非对映选择性）具有很高的活性。一锅法醇氧化-维蒂希反应制得的芳基，杂芳基，烯丙基和烷基醇。该转化利用空气作为化学计量的氧化剂，廉价的催化剂可以回收和再利用。
• One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
  作者：Xiaochun Yu、Shun Wang、Weijie Ding、Juan Hu、Huile Jin

  DOI：10.1055/s-0036-1590904

  日期：2018.1

  reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields. A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O2 in air as oxidant. The solvent mixture of acetonitrile

  摘要 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极好的收率形成相应的α，β-不饱和酯，酮和腈。 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极
• Atomically precise palladium nanocluster catalyzed tandem oxidation processes of alcohols and phosphorous ylides: Facile access to α,β-unsaturated esters
  作者：Taiping Gao、Jialei Du、Wenyan Liu、Mingxia Ren

  DOI：10.1016/j.tetlet.2020.152385

  日期：2020.10

  mesoporous silica nanosphere supported palladium nanocluster was synthesized through a simple impregnation method and well characterized. The as prepared catalyst shows excellent catalytic performance in tandem oxidation process (TOP) of alcohol and phosphorous ylide, which provides an efficient access to α,β-unsaturated esters with high yields utilizes 1 atmosphere of molecular oxygen as sole oxidant

  通过简单的浸渍方法合成了介孔二氧化硅纳米球负载的钯纳米簇，并对其进行了很好的表征。所制备的催化剂在醇和亚磷酰的串联氧化过程（TOP）中显示出优异的催化性能，利用1个大分子的分子氧作为唯一氧化剂，可以高效地高效获得α，β-不饱和酯。这项工作代表了原子精确的钯纳米簇催化的醇和磷化磷的串联氧化过程的第一个实例，有望为串联反应中的纳米团簇开辟新的视野。
• ATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis
  作者：Peter W. Moore、Christopher D. G. Read、Paul V. Bernhardt、Craig M. Williams

  DOI：10.1002/chem.201800531

  日期：2018.3.26

  commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and

  该魔网格里菲斯四ñ丙基过钌酸铵（TPAP）催化剂已被合成界广泛采用，主要用于将醇氧化为醛和酮，还用于多种其他合成转化（例如二醇裂解，异构化，亚胺形成和杂环合成）。在广泛的反应范围，官能团耐受性，温和条件和商业催化剂供应上已经锻造了这种受欢迎度。但是，由于无法防止的缓慢分解，TPAP的轻度不稳定会导致制备，储存和反应重现性问题。为了寻找有利于催化剂寿命的属性，制备了多种新颖的过硼酸盐。随后的评估发现了一组易于合成，稳定的台式过氧化磷鎓（ATP3和MTP3），它们反映了TPAP的反应活性，
• Phosphine-mediated partial reduction of alkynes to form both (<i>E</i>)- and (<i>Z</i>)-alkenes
  作者：Brett M. Pierce、Brittany F. Simpson、Kane H. Ferguson、Rachel E. Whittaker

  DOI：10.1039/c8ob01848k

  日期：——

  phosphine-mediated partial reduction of alkynyl carbonyls to the corresponding alkenes was developed. Tuning of the reaction conditions led to either the (E)- or (Z)-diastereomer with high selectivity. A range of alkynyl esters, amides, and ketones were reduced to form alkenes in good to high yields and with excellent functional group tolerance.

  已开发出温和的，膦介导的炔基羰基部分还原为相应的烯烃的方法。反应条件的调节导致具有高选择性的（E）-或（Z）-非对映异构体。还原了一系列炔基酯，酰胺和酮，以高到高收率并具有出色的官能团耐受性形成了烯烃。