methyl (E)-3-(2’-(bromomethyl)phenyl)acrylate | 146793-49-9

• 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: methyl (E)-3-(2’-(bromomethyl)phenyl)acrylate
• 英文别名: 3-(2-bromomethylphenyl)acrylic acid methyl ester；(E)-methyl 3-(2-(bromomethyl)phenyl)acrylate；methyl o-(bromomethyl)cinnamate；2-Propenoic acid, 3-[2-(bromomethyl)phenyl]-, methyl ester；methyl (E)-3-[2-(bromomethyl)phenyl]prop-2-enoate
• CAS: 146793-49-9
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: APTKTAVEUREZBJ-VOTSOKGWSA-N

物化性质

• 沸点：
  328.8±22.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  methyl (E)-3-(2’-(bromomethyl)phenyl)acrylate 在 二异丁基氢化铝 、 potassium carbonate 、 盐酸 、 水 作用下， 以 乙醚 、 正己烷 、 水 、 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到(E)-3-(2-(bromomethyl)phenyl)prop-2-en-1-ol
  参考文献：
  名称：

  A Chiral Bidentate sp2-N Ligand, Naph-diPIM: Application to CpRu-Catalyzed Asymmetric Dehydrative C-, N-, and O-Allylation

  摘要：

  DOI：

  10.1002/anie.201100772
• 作为产物：
  描述：

  2-甲基苯甲醛 在 哌啶 、 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 生成 methyl (E)-3-(2’-(bromomethyl)phenyl)acrylate
  参考文献：
  名称：

  邻位取代肉桂酸酯的串联还原+环化

  摘要：

  通过Stryker's试剂还原邻位取代的肉桂酸酯，形成烯醇铜，然后进行分子内羟醛型环化，可在一锅中成功生成茚满和四氢化萘环。该串联反应通常是非对映选择性的，并提供良好的产率。

  DOI：

  10.1016/j.tetlet.2011.08.039

文献信息

• Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines
  作者：Le-Le Wang、Hua-Bin Han、Zhao-Hui Cui、Jun-Wei Zhao、Zhan-Wei Bu、Qi-Lin Wang

  DOI：10.1021/acs.orglett.9b04398

  日期：2020.2.7

  chalcone-based pyridinium salts have been successfully exploited, which could smoothly participate in the highly diastereoselective dearomatization with binucleophilic enaminones by taking advantage of their multiple reactive sites to construct bibridged benzoazepines in up to 89% yields. The key to the success was the skillful and unprecedented C-3 functionalization of the new pyridinium salts. This work

  新的基于查尔酮的吡啶鎓盐已被成功开发，可以利用它们的多个反应位点以高达89％的产率构建双桥苯并氮杂卓，从而顺利地参与双亲核性烯胺酮的高度非对映选择性脱芳香化作用。成功的关键是新型吡啶盐的C-3功能化和空前的熟练。这项工作不仅提供了一种新颖的吡啶鎓盐合成子，而且实现了吡啶鎓盐的第一个C-3官能化，从而以高合成效率构建了复杂且具有挑战性的双桥苯并氮杂。
• Synthesis of Tetrahydroisoquinolines by Visible-Light-Mediated 6-exo-trig Cyclization of α-Aminoalkyl Radicals
  作者：Michael Grübel、Christian Jandl、Thorsten Bach

  DOI：10.1055/s-0039-1690006

  日期：2019.9

  Starting from the respective tertiary α-silylmethyl amines, the intramolecular cyclization of α-aminoalkyl radicals to Michael acceptors produced tetrahydroisoquinolines. The reaction conditions included the use of 5 mol% of an iridium photoredox catalyst, dimethylformamide as the solvent, and equimolar amounts of water and cesium carbonate as the additives. 13 substrates were synthesized from ort

  从各自的叔α-甲硅烷基甲基胺开始，α-氨基烷基自由基与迈克尔受体的分子内环化产生四氢异喹啉。反应条件包括使用5 mol%的铱光氧化还原催化剂，二甲基甲酰胺作为溶剂，以及等摩尔量的水和碳酸铯作为添加剂。在涉及羰基缩合、自由基溴化和仲 α-甲硅烷基甲基胺取代的三步程序中，从邻烷基苯甲醛合成了 13 种底物。在优化光环化后，该反应以中等至高产率（41-83%）提供四氢异喹啉。面部非对映选择性（dr ≅ 80：20) 用手性底物观察到，晶体结构为主要非对映异构体的相对构型提供了证据。提出了一种将电子直接转移到光激发金属催化剂的催化循环。
• [EN] PYRROLIDIN-2-ON DERIVATIVES AS EP4 RECEPTOR AGONISTS<br/>[FR] DERIVES DE PYRROLIDINE-2-ONE EN TANT QU'AGONISTES DU RECEPTEUR EP4
  申请人：MERCK FROSST CANADA INC

  公开号：WO2004037813A1

  公开（公告）日：2004-05-06

  This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors having structural formula (I), their use or a formulation thereof in the treatment of glaucoma and other conditions which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.

  本发明涉及EP4型前列腺素E2受体的高效选择性激动剂，其结构式为（I），以及它们或其制剂在治疗青光眼和其他与患者眼内压升高相关的疾病中的应用。本发明还涉及使用本发明化合物介导成骨细胞和破骨细胞的骨建模和重塑过程。
• Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor
  作者：Hélène Juteau、Yves Gareau、Marc Labelle、Claudio F Sturino、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Kathleen M Metters

  DOI：10.1016/s0968-0896(01)00110-9

  日期：2001.8

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Comparison between two classes of selective EP3 antagonists and their biological activities
  作者：Michel Belley、Chi Chung Chan、Yves Gareau、Michel Gallant、Hélène Juteau、Karine Houde、Nicolas Lachance、Marc Labelle、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Gillian M. Greig、Deborah Slipetz、Robert Gordon、Nathalie Chauret、Chun Li、Robert J. Zamboni、Kathleen M. Metters

  DOI：10.1016/j.bmcl.2006.08.025

  日期：2006.11

  Two different series of very potent and selective EP3 antagonists have been reported: a novel series of ortho-substituted cinnamic acids [Belley, M., Gallant, M., Roy, B., Houde, K., Lachance, N., Labelle, M., Trimble, L., Chauret, N., Li, C., Sawyer, N., Tremblay, N., Lamontagne, S., Carriere, M.-C., Denis, D., Greig, G. M., Slipetz, D., Metters, K. M., Gordon, R., Chan, C. C., Zamboni, R. J. Bioorg. Med. Chem. Lett. 2005, 15, 527] and the acylsulfonamides of ortho-(arylmethyl)cinnamates. [(a) Juteau, H., Gareau, Y., Labelle, M., Sturino, C. F., Sawyer, N., Tremblay, N., Lamontagne, S., Carriere, M.-C., Denis, D., Metters, K. M. Bioorg. Med. Chem. 2001, 9, 1977; (b) Juteau, H., Gareau, Y., Labelle, M., Lamontagne, S., Tremblay, N., Carriere, M.-C., Denis, D., Sawyer, N., Metters, K. M. Bioorg. Med. Chem. Lett. 2001, 11, 747] The structural differences between the two series, along with their biological activity in vivo, in vitro, and metabolism, are analyzed. Some of those compounds, including hybrids containing the best structural features of both series, possess K-i as low as 0.6 nM on the EP3 receptor. (c) 2006 Elsevier Ltd. All rights reserved.