(Z)-methyl 2-(bromomethyl)-3-(4-bromophenyl)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-bromophenyl)acrylate
• 英文别名: (z)-Methyl-2-(bromomethyl)-3-(4-bromophenyl)acrylate；methyl (Z)-2-(bromomethyl)-3-(4-bromophenyl)prop-2-enoate
• 化学式: C₁₁H₁₀Br₂O₂
• 分子量: 334.007
• InChiKey: WWVITQLLAJMYTQ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 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)-methyl 2-(bromomethyl)-3-(4-bromophenyl)acrylate 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 (E)-3-(4-bromobenzylidene)-1-propylazetidin-2-one
  参考文献：
  名称：

  Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer

  摘要：

  A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of the synthesized compounds were characterized by H-1, C-13 NMR, and MS; and their antifungal activity were evaluated against Alternaria solani Sorauer. These antifungal data were subjected to a quantitative structure-activity relationship (QSAR) analysis using Codessa software on the basis of the results from B3LYP/6-31G(d,p) quantum calculations. The best regressive model revealed that potentially more active compounds should have low dipole moments and Q(C-min) (minimal net atomic charge for a C atom), and high Q(O-max) (maximal net atomic charge for an O atom) and Q(N-min) (minimal net atomic charge for an N atom). The most potent compound 7k could lead to intracellular accumulation of reactive oxygen species, dissipation of mitochondrial transmembrane potential, and an autophagy-like cell death process in A. solani Sorauer. Taken together, these results laid the foundation for further design of improved crop-protection agents based on this hybrid scaffold. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.11.003
• 作为产物：
  描述：

  2-[(4-bromo-phenyl)-hydroxy-methyl]-acrylic acid methyl ester 在 lithium bromide 作用下， 生成 (Z)-methyl 2-(bromomethyl)-3-(4-bromophenyl)acrylate
  参考文献：
  名称：

  从多功能烯丙基鏻盐微波辅助合成 (E)-α-甲基链烯酸酯骨架

  摘要：

  描述了一种方便和通用的微波辅助方法，用于在碱性水介质中从烯丙基鏻盐合成立体化学定义的 α-甲基链烯酸和酯。酸或酯的选择性制备取决于反应中使用的碱（NaOH 或 NaHCO3），并且可以在不存在氢化物和还原剂的温和条件下以良好到极好的收率实现。© 2012 Wiley Periodicals, Inc. 杂原子化学 23:179–186, 2012; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21001

  DOI：

  10.1002/hc.21001

文献信息

• Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization
  作者：P. Veeraraghavan Ramachandran、Daniel R. Nicponski

  DOI：10.1039/c4cc05765a

  日期：——

  An auto-catalytic domino reaction involving an aza-Michael reaction, proton transfer, and lactonization furnishing α-aminomethyl-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

  一种涉及aza-Michael反应、质子转移和内酯化的自催化多米诺反应，以近定量的收率和优秀的对映选择性提供了α-氨基甲基-γ-丁内酯。

• 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
• Synthesis and biological evaluation of novel 2-alkoxycarbonylallylester phosphonium derivatives as potential anticancer agents
  作者：Zachary S. Gardner、Tanner J. Schumacher、Conor T. Ronayne、Greeshma P. Kumpati、Michael J. Williams、Akira Yoshimura、Hithardha Palle、Chinnadurai Mani、Jon Rumbley、Venkatram R. Mereddy

  DOI：10.1016/j.bmcl.2021.128136

  日期：2021.8

  allyl bromides and aryl phosphines as mitochondria targeting anticancer agents. In vitro cell proliferation inhibition studies on various solid tumor cell lines indicate that most of the compounds exhibit IC50 values in µM concentrations. Further studies reveal that β-substituted BH bromide derived phosphonium derivatives enhance the biological activity to low µM IC50 values. In vitro metabolic studies

  已经从 Baylis-Hillman (BH) 反应衍生的烯丙基溴和芳基膦合成了几种鏻衍生物作为靶向抗癌剂的线粒体。对各种实体肿瘤细胞系的体外细胞增殖抑制研究表明，大多数化合物在 μM 浓度下表现出 IC 50值。进一步的研究表明，β-取代的 BH 溴化物衍生的鏻衍生物将生物活性提高到低 µM IC 50值。体外 代谢研究表明，先导候选化合物16 抑制线粒体 ATP 的产生，增加线粒体膜内的质子泄漏，并以浓度依赖性方式消除备用呼吸能力。
• A phenacrylate scaffold for tunable thiol activation and release
  作者：Rathinam K. Sankar、Rohan S. Kumbhare、Allimuthu T. Dharmaraja、Harinath Chakrapani

  DOI：10.1039/c4cc07343f

  日期：——

  A scaffold for biological thiol mediated tunable activation and release of a cargo is reported.

  报道了一种用于生物硫醇介导的可调节激活和释放载荷的支架。
• Expedient Synthesis of N-Fused Indoles through an Intramolecular [3+2]-Cycloaddition Approach
  作者：Raghavachary Raghunathan、Subban Kathiravan

  DOI：10.1055/s-0029-1219551

  日期：2010.4

  A variety of N-fused indolo pyrrolo-pyrroles and pyrrolo-pyrrolizidines were synthesized by intramolecular 1,3-dipolar cycloaddition reaction of azomethine ylide generated from N-alkenylindole carbaldehyde which were prepared by the N-alkylation of indole 2-aldehyde with Baylis-Hillman bromides.

  通过分子内 1,3- 双极环加成反应，合成了多种 N-融合的吲哚吡咯并吡咯并吡咯烷，这些化合物是由 N-烯基吲哚甲醛与巴氏-希尔曼溴化物进行 N-烷基化反应生成的偶氮甲基醯胺。