methyl 2-methyl-2-(4-vinylphenyl)propanoate | 1298022-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-methyl-2-(4-vinylphenyl)propanoate
• 英文别名: Methyl 2-(4-ethenylphenyl)-2-methylpropanoate
• CAS: 1298022-54-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: XGXZAXRWPOXJRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 2-methyl-2-(4-vinylphenyl)propanoate 在 dimethyl sulfide borane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以83%的产率得到4-(2-羟基乙基)-ALPHA,ALPHA-二甲基苯基-乙酸甲酯
  参考文献：
  名称：

  Alternative Synthesis of Bilastine

  摘要：

  [image omitted] A new and efficient synthesis of the non-sedating histamine H1 receptor antagonist Bilastine is reported. The new route employs a convergent strategy, with a longest linear sequence of five steps, giving slightly improved yields over the previous routes. The use of anhydrous metal-halogen exchange, hazardous ethylene oxide, and a tedious protection of the carboxylic acid function are all avoided.

  DOI：

  10.1080/00397911.2010.486506
• 作为产物：
  描述：

  三丁基乙烯基锡 、 2-(4-溴苯基)-2,2-二甲基乙酸甲酯 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以86%的产率得到methyl 2-methyl-2-(4-vinylphenyl)propanoate
  参考文献：
  名称：

  Alternative Synthesis of Bilastine

  摘要：

  [image omitted] A new and efficient synthesis of the non-sedating histamine H1 receptor antagonist Bilastine is reported. The new route employs a convergent strategy, with a longest linear sequence of five steps, giving slightly improved yields over the previous routes. The use of anhydrous metal-halogen exchange, hazardous ethylene oxide, and a tedious protection of the carboxylic acid function are all avoided.

  DOI：

  10.1080/00397911.2010.486506

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
  作者：Mincong Su、Xia Huang、Chuanhu Lei、Jian Jin

  DOI：10.1021/acs.orglett.1c04018

  日期：2022.1.14

  nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used

  已经使用（杂）芳基溴化物和乙酸乙烯酯作为偶联伙伴实现了镍催化的还原交叉偶联。这种温和、适用的方法提供了获得各种乙烯基芳烃、杂芳烃和苯并杂环化合物的可靠途径，这将扩大精细化学品和聚合物前体的化学空间。重要的是，使用了一种可持续溶剂二甲基异山梨醇，从绿色化学的角度来看，这使得该协议更具吸引力。
• [EN] PROCESS AND INTERMEDIATES FOR THE PREPARATION OF BILASTINE<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES POUR LA PRÉPARATION DE BILASTINE
  申请人：FAES FARMA SA

  公开号：WO2020020873A1

  公开（公告）日：2020-01-30

  The invention relates to a process for preparing a compound of (III) wherein X is a leaving group; and R1 is C1-C6 alkyl; which comprises oxidative rearrangement of a compound of formula (II) or a solvate thereof Compounds of formula (III) are key intermediates in the synthesis of Bilastine.

  该发明涉及一种制备化合物(III)的方法，其中X是一个离去基团，而R1是C1-C6烷基；该方法包括将式(II)的化合物或其溶剂化物进行氧化重排。公式(III)的化合物是合成Bilastine的关键中间体。
• PROCESS AND INTERMEDIATES FOR THE PREPARATION OF BILASTINE
  申请人：FAES FARMA, S.A.

  公开号：EP3599235A1

  公开（公告）日：2020-01-29

  The invention relates to a process for preparing a compound of (III) wherein X is a leaving group; and R1 is C1-C6 alkyl; which comprises oxidative rearrangement of a compound of formula (II) or a solvate thereof Compounds of formula (III) are key intermediates in the synthesis of Bilastine.

  本发明涉及一种制备（III）化合物的工艺 其中 X 是离去基团；和 R1 是 C1-C6 烷基； 其中包括式（II）化合物或其溶液的氧化重排 式（III）化合物是合成比拉斯汀的关键中间体。
• Process and intermediates for the preparation of bilastine
  申请人：FAES FARMA, S.A.

  公开号：US11370742B2

  公开（公告）日：2022-06-28

  The invention relates to a process for preparing a compound of (III) wherein X is a leaving group; and R1 is C1-C6 alkyl; which comprises oxidative rearrangement of a compound of formula (II) or a solvate thereof Compounds of formula (III) are key intermediates in the synthesis of Bilastine.

  本发明涉及一种制备（III）化合物的工艺 在其中 X 是离去基团；和 R1 是 C1-C6 烷基； 其中包括式(II)化合物或其溶液的氧化重排 式 (III) 化合物是合成比拉斯汀的关键中间体。
• Alternative Synthesis of Bilastine
  作者：Steven J. Collier、Xiang Wu、Zhiying Poh、Gurubatham Abraham Rajkumar、Larry Yet

  DOI：10.1080/00397911.2010.486506

  日期：2011.4.5

  [image omitted] A new and efficient synthesis of the non-sedating histamine H1 receptor antagonist Bilastine is reported. The new route employs a convergent strategy, with a longest linear sequence of five steps, giving slightly improved yields over the previous routes. The use of anhydrous metal-halogen exchange, hazardous ethylene oxide, and a tedious protection of the carboxylic acid function are all avoided.