(Z)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate | 871893-64-0

• 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)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate
• 英文别名: Ethyl 2-bromo-3-(4-methoxyphenyl)prop-2-enoate；ethyl 2-bromo-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 871893-64-0
• 化学式: C₁₂H₁₃BrO₃
• 分子量: 285.137
• InChiKey: LYFMLDYMLOOFRK-UHFFFAOYSA-N

物化性质

• 沸点：
  363.0±27.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以84%的产率得到(Z)-2-bromo-3-(p-anisyl)propenoic acid
  参考文献：
  名称：

  Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones

  摘要：

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.

  DOI：

  10.1021/ol1008813
• 作为产物：
  描述：

  (2RS:3SR)-2.3-dibromo-3-(4-methoxy-phenyl)-propionic acid ethyl ester 在 N,N-二甲基甲酰胺 作用下， 反应 0.17h， 生成 对甲氧基肉桂酸乙酯 、 (Z)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate
  参考文献：
  名称：

  Versatile Transformations of α,β-Dibromoesters and Ketones in Basic Media under Microwave Irradiation

  摘要：

  根据反应介质的不同，δ,δ-二溴酯在微波辐照下可选择性地生成δ-溴烯烃、烯烃或(E)-δ-溴苯乙烯。相应的酮可选择性地生成δ-溴酮。

  DOI：

  10.1055/s-2003-41054

文献信息

• A new route to α-trifluoromethyl-α,β-unsaturated esters
  作者：Xingang Zhang、Feng-Ling Qing、Yonggang Yang、Jiang Yu、Xiang-Kai Fu

  DOI：10.1016/s0040-4039(00)00279-3

  日期：2000.4

  The treatment of α-bromo-α,β-unsaturated esters with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters.

  在DMF / HMPA中用FSO 2 CF 2 CO 2 Me和CuI处理α-溴-α，β-不饱和酯构成了制备α-三氟甲基-α，β-不饱和酯的新合成方案。
• Synthesis of 2‘,3‘-Dideoxy-2‘-trifluoromethylnucleosides from α-Trifluoromethyl-α,β-unsaturated Ester
  作者：Xingang Zhang、Feng-Ling Qing、Yihua Yu

  DOI：10.1021/jo005520r

  日期：2000.10.1

  beta-unsaturated esters 3. The trifluoromethylation of (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (2e), which is derived from 1-(R)-glyceraldehyde acetonide, yields the key intermediate alpha-trifluoromethyl-alpha,beta-unsaturated esters 3e. This is transformed into anomeric acetates 8a and 8b and is used for the synthesis of a number of 2', 3'-dideoxy-2'-trifluoromethylnucleosides

  在DMF / HMPA中用FSO（2）CF（2）CO（2）Me和CuI处理α-溴-α，β-不饱和酯2构成了制备α-三氟甲基-α，β的新合成方案-不饱和酯3.（Z）/（E）-乙基3-[（（S）-2,2-二甲基-1,3-二氧戊环-4-基] -2-溴-2-丙酸酯（2e）的三氟甲基化衍生自1-（R）-甘油醛丙酮化物的）生成关键中间体α-三氟甲基-α，β-不饱和酯3e。将其转化为异头乙酸酯8a和8b，并用于合成许多2'，3'-二脱氧-2'-三氟甲基核苷。
• Titanocene(III) chloride mediated radical induced addition-elimination route to the synthesis of racemic and optically active trisubstituted tetrahydrofurans: Formal synthesis of magnofargesin and 7′-epimagnofargesin
  作者：P CHAKRABORTY、S K MANDAL、S C ROY

  DOI：10.1007/s12039-016-1106-0

  日期：2016.7

  Titanocene(III) Chloride mediated radical induced synthesis of 4-benzylidene substituted tetrahydrofuran, a typical lignan skeleton, has been accomplished in good yield through addition-elimination route in racemic as well as in optically active forms. The method has been applied to the synthesis of furano lignans, magnofargesin (1) and 7′-epimagnofargesin (2) in optically active forms. Titanocene(III)

  通过外消旋和旋光形式的加成-消除途径，已经成功地完成了钛茂新星（III）氯化物介导的自由基诱导的4-苄叉基取代的四氢呋喃（典型的木脂素骨架）的合成。该方法已被应用于呋喃木脂素的合成，magnofargesin（1）和7 ' -epimagnofargesin（2以光学活性形式）。 通过外消旋和旋光形式的加成-消除途径，已经成功地完成了钛茂新星（III）氯化物介导的自由基诱导的4-苄叉基取代的四氢呋喃（典型的木脂素骨架）的合成。该方法已用于合成光学活性形式的呋喃聚糖木脂素，厚朴素和7′-表脂素。
• The reaction of substituted ethyl α-bromocinnamates with tetrabutyl ammonium fluoride
  作者：Yan Liang、Ying Peng Zhang、Wei Yu

  DOI：10.1016/j.cclet.2012.05.015

  日期：2012.7

  -bromocinnamates with tetrabutyl ammonium fluoride (TBAF) was influenced largely by the position of the substituent at the phenyl ring. While the substrates without an ortho substituent at the phenyl ring were transformed to the corresponding β -fluoro ethyl cinnamates under the reaction conditions, the presence of an ortho substituent only resulted in the formation of ethyl 3-phenylpropiolate derivatives

  摘要α-溴代肉桂酸乙酯与四丁基氟化铵（TBAF）的反应在很大程度上受取代基在苯环上的位置的影响。虽然在反应条件下将在苯环上没有邻取代基的底物转化为相应的β-氟乙基肉桂酸酯，但是邻取代基的存在仅导致3-苯基丙酸乙酯衍生物的形成。由于甲氧基的供电子作用，丙烯酸2-溴-3-（4-甲氧基苯基）乙酯的反应也不能递送氢氟化产物。
• Preparation of α-Bromoacrylates: One-Pot Procedure for the Synthesis of Conjugated Acetylenic Carboxylates from Aldehydes with Ph₃P/Br₃CCO₂Et
  作者：Doo Jang、Joong-Gon Kim、Dong Kang

  DOI：10.1055/s-2008-1032070

  日期：2008.2

  established the optimal conditions for the Wittig reaction for synthesizing α-bromoacrylates with a high selectivity, and developed a simple and efficient one-pot procedure for preparing various conjugated acetylenic carboxylates in moderate to high yields.

  我们已经建立了 Wittig 反应以高选择性合成 α-溴丙烯酸酯的最佳条件，并开发了一种简单高效的一锅法以中等至高收率制备各种共轭炔羧酸。