(Z)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate

• 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)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate
• 英文别名: methyl (Z)-2-(bromomethyl)-3-[4-(trifluoromethyl)phenyl]prop-2-enoate
• 化学式: C₁₂H₁₀BrF₃O₂
• 分子量: 323.109
• InChiKey: FHUWYZOVPWOTLU-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate 在 indium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 cis-β-(4-fluoromethylphenyl)-γ-phenyl-α-methylene-γ-butyrolactone
  参考文献：
  名称：

  Syntheses of β- and γ-fluorophenyl cis- and trans-α-methylene-γ-butyrolactones

  摘要：

  Preparation of a series of cis-gamma-fluorophenyl-beta-phenyl-alpha-methylene-gamma-butyrolactones is reported via 'allylboration' of fluorobenzaldehydes with (E)-methyl 3-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)acrylate. The corresponding trans-gamma-fluorophenyl lactones were prepared either (i) via 'allylboration' using the (Z)-reagents or (ii) via an indium triflate-mediated isomerization of the cis-products. The difficulty in isomerizing difluorinated cis-products confirms the probable intermediacy of carbocations. Finally, the synthesis of cis-beta-fluorophenyl-gamma-phenyl-alpha-methylene-gamma-butyrolactones was achieved via an indium-catalyzed allylation-lactonization of aldehydes with (Z)-2-(bromomethyl)-3-(fluorophenyl)acrylates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.07.106
• 作为产物：
  描述：

  methyl 2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)acrylate 在 硫酸 、 氢溴酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (Z)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate
  参考文献：
  名称：

  从 Baylis-Hillman 溴化物高效合成 N-烯丙基化 2-硝基亚氨基咪唑烷类似物

  摘要：

  摘要 使用碳酸钾作为碱，可以有效地制备各种 Baylis-Hillman 衍生的新型 N-烯丙基化 2-硝基亚氨基咪唑烷类似物。简单的后处理程序、优异的收率和温和的反应条件是该方法的显着特点。筛选所有合成的化合物对四龄蚊子幼虫库蚊的杀幼虫活性。图形概要

  DOI：

  10.1080/00397911.2016.1255333

文献信息

• Efficient synthesis of <i>N</i>-allylated 2-nitroiminoimidazolidine analogues from Baylis–Hillman bromides
  作者：Sriramoju Bharath Kumar、Chebolu Naga Sesha Sai Pavan Kumar、Amlipur Santhoshi、Koochana Pranay Kumar、U. S. N. Murthy、Vaidya Jayathirtha Rao

  DOI：10.1080/00397911.2016.1255333

  日期：2017.1.17

  ABSTRACT Various Baylis–Hillman–derived new N-allylated 2-nitroiminoimidazolidine analogs were efficiently prepared using potassium carbonate as base. Simple workup procedure, excellent yields, and mild reaction conditions are the salient features of this method. All the synthesized compounds are screened for their larvicidal activity on fourth instar mosquito larvae, Culex quinquefasciatus. GRAPHICAL

  摘要 使用碳酸钾作为碱，可以有效地制备各种 Baylis-Hillman 衍生的新型 N-烯丙基化 2-硝基亚氨基咪唑烷类似物。简单的后处理程序、优异的收率和温和的反应条件是该方法的显着特点。筛选所有合成的化合物对四龄蚊子幼虫库蚊的杀幼虫活性。图形概要
• Rhodium-Catalyzed Enantioselective Hydrogenation of β-Phthalimide Acrylates to Synthesis of β²-Amino Acids
  作者：Hanmin Huang、Xiongcai Liu、Jun Deng、Min Qiu、Zhuo Zheng

  DOI：10.1021/ol0612399

  日期：2006.7.1

  [Structure: see text] The enantioselective hydrogenation of beta-phthalimide acrylates provides the corresponding chiral beta2-amino acids in excellent enantiomeric excess catalyzed by Rh-monophosphorus.

  [结构：见正文]β-邻苯二甲酰亚胺丙烯酸酯的对映选择性氢化，在Rh-单磷的催化下，以优异的对映体过量提供了相应的手性β2-氨基酸。
• Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors
  作者：Amlipur Santhoshi、Budde Mahendar、Saidulu Mattapally、Partha Sarathi Sadhu、Sanjay Kumar Banerjee、Vaidya Jayathirtha Rao

  DOI：10.1016/j.bmcl.2014.02.073

  日期：2014.4

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.
• Syntheses of β- and γ-fluorophenyl cis- and trans-α-methylene-γ-butyrolactones
  作者：P. Veeraraghavan Ramachandran、Hari Narayanan G. Nair、Pravin Gagare

  DOI：10.1016/j.tetlet.2014.07.106

  日期：2014.10

  Preparation of a series of cis-gamma-fluorophenyl-beta-phenyl-alpha-methylene-gamma-butyrolactones is reported via 'allylboration' of fluorobenzaldehydes with (E)-methyl 3-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)acrylate. The corresponding trans-gamma-fluorophenyl lactones were prepared either (i) via 'allylboration' using the (Z)-reagents or (ii) via an indium triflate-mediated isomerization of the cis-products. The difficulty in isomerizing difluorinated cis-products confirms the probable intermediacy of carbocations. Finally, the synthesis of cis-beta-fluorophenyl-gamma-phenyl-alpha-methylene-gamma-butyrolactones was achieved via an indium-catalyzed allylation-lactonization of aldehydes with (Z)-2-(bromomethyl)-3-(fluorophenyl)acrylates. (C) 2014 Elsevier Ltd. All rights reserved.
• New Allyldithiocarbimates: Synthesis, Structure and Antifungal Activity against Phakopsora pachyrhizi and Hemileia vastatrix
  作者：Antonio Vidigal、Mayura Rubinger、Lucas da Silva、Laércio Zambolim、Arthur Pereira、Silvana Guilardi、Rafael Souza、Javier Ellena

  DOI：10.21577/0103-5053.20190234

  日期：——

  Twelve tetraphenylphosphonium allyldithiocarbimates were synthesized and fully characterized by high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), infrared and nuclear magnetic resonance (NMR) spectroscopies. The spectroscopic data indicated that the allyldithiocarbimate anions present Z configuration, as confirmed by X-ray crystallography. These new compounds inhibited the germination of Phakopsora pachyrhizi and Hemileia vastatrix at very low doses, with IC50 (concentration to achieve 50% of inhibition of spore germination) values ranging from 0.028 to 0.166 mmol L-1, and IC50 (concentration to achieve 90% of inhibition of spore germination) values varying from 0.156 to 0.528 mmol L-1. Allyldithiocarbimate salts are lead compounds for the development of new antifungals for coffee leaf rust and Asian soybean rust. devastating plant diseases with limited control options.