(Z)-ethyl 3-(2-bromophenyl)acrylate | 99134-35-7

• 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: (Z)-ethyl 3-(2-bromophenyl)acrylate
• 英文别名: ethyl (Z)-3-(2-bromophenyl)prop-2-enoate
• CAS: 99134-35-7
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: OVVAHDSHDPZGMY-FPLPWBNLSA-N

物化性质

• 沸点：
  322.0±17.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-(2-bromophenyl)acrylate 在 四丁基碘化铵 氢氧化钾 、 sodium tetrahydroborate 、 4-硝基苯甲酸酐 、 四丁基碘化铵 、 1,2-二溴乙烷 、 nickel dibromide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 42.0h， 生成 (Z)-3-[2-(3-hydroxybutyl)phenyl]prop-2-enoic acid η-lactone
  参考文献：
  名称：

  Access to a new family of medium ring aromatic lactones

  摘要：

  We report a new method for preparation of hydroxyacids as precursors of benzolactones using a simple and an efficient electrochemical step. This gives in only four steps six- to eleven-membered lactones with high isolated yields from conveniently substituted aryl bromides. The lactonisation was performed according to the Yamamoto's process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.071
• 作为产物：
  描述：

  邻溴苯甲醛 、 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81%的产率得到(Z)-ethyl 3-(2-bromophenyl)acrylate
  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

• Diazo Reagents in Copper(I)-Catalyzed Olefination of Aldehydes
  作者：Hélène Lebel、Michaël Davi

  DOI：10.1002/adsc.200800381

  日期：2008.10.6

  The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility

  描述了在碘化铜（I）存在下使用重氮试剂和三苯基膦将醛烯化以合成不饱和酮，酯，酰胺和膦酸酯。对于多种脂族，芳族和杂芳族醛，均获得了良好的E：Z选择性和良好的收率。该反应还显示出优异的官能团相容性，并且在酮，硝基，胺，醚，缩醛，硫醚和卤化物基团的存在下醛被选择性地反应。与先前报道的昂贵的过渡金属络合物相比，使用成本有效的铜盐作为催化剂是有利的。该方法用于scutifoliamide A的全合成，scutifoliamide A是一种具有抗真菌活性的生物活性化合物。
• Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions
  作者：Chao Song、Chen Yang、Hua Zeng、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.orglett.8b01406

  日期：2018.7.6

  Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

  Rh（III）催化的与α-重氮-α-膦酰基乙酸酯结合的烯胺酮定向的C–H偶联已用于鉴定氟化物介导的膦酰基化的C–C偶联反应，用于合成4-羟基-1-萘甲酸酯。还实现了α-膦酰基乙酸酯和苯甲醛的分子间CC偶联，用于（E）-选择性α，β-不饱和酯的合成。
• Palladium-Catalyzed Tandem Reactions To Form 1-Vinyl-1<i>H</i>-isochromene Derivatives¹
  作者：Roger Mutter、Ian B. Campbell、Eva M. Martin de la Nava、Andy T. Merritt、Martin Wills

  DOI：10.1021/jo0011991

  日期：2001.5.1

  also an essential choice as it furnishes the appropriate reactivity to promote allylic substitution after the aryl coupling process. The use of more effective leaving groups, such as acetate, results in reaction of the allylic group, and no aryl coupling is observed. Through the appropriate selection of phosphine ligand and solvent, either the cyclized isochromene product or the noncyclized intermediate

  松果酮与叔丁基二甲基（3-（2-溴苯基）烯丙氧基）硅烷的钯催化反应可直接形成1-乙烯基-3-叔丁基-1H-异戊烯。这是酮芳基化，然后烯醇与烯丙基体系分子内环化的结果。使用二酰胺锂碱似乎对成功至关重要。叔丁基二甲基甲硅烷基保护基也是必不可少的选择，因为它在芳基偶联过程之后提供适当的反应性来促进烯丙基取代。使用更有效的离去基团，例如乙酸酯，导致烯丙基的反应，并且未观察到芳基偶联。通过膦配体和溶剂，无论是环化的苯并吡喃产物或中间noncyclized的适当选择可以选择性地形成。
• Chromatography-Free Wittig Reactions Using a Bifunctional Polymeric Reagent
  作者：Peter Shu-Wai Leung、Yan Teng、Patrick H. Toy

  DOI：10.1021/ol1021614

  日期：2010.11.5

  The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after

  已经制备了带有两个不同试剂基团的聚苯乙烯的第一个例子。该膦和胺官能化的材料用于与醛和α-卤代酯，-酮或-酰胺的一锅法Wittig反应中。由于聚合物的非均质性质，仅在过滤和除去溶剂后，就可以以优异的收率以基本纯净的形式分离出这些反应的所需烯烃产物。
• Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation
  作者：Tao Song、Stellios Arseniyadis、Janine Cossy

  DOI：10.1002/chem.201800920

  日期：2018.6.7

  The synthesis of diversely substituted five‐membered ring succinimide derivatives is reported featuring a direct, base‐free, palladium‐catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all‐carbon α‐quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic

  据报道，具有不同取代基的五元环琥珀酰亚胺衍生物的合成具有直接的，无碱的，钯催化的不对称烯丙基烷基化作用。该方法可以直接获得所需的杂环骨架，该骨架具有全碳α-季立体中心，且收率高，对映选择性极好。为了进一步证明该方法的合成效用，使用选择性转化将烯丙基化的产物进一步转化为各种通用的手性构件，包括手性吡咯烷和螺环衍生物。