(Z)-methyl 2-(bromomethyl)-3-(3-fluorophenyl)acrylate | 1609257-70-6

• 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-(3-fluorophenyl)acrylate
• 英文别名: methyl (Z)-2-(bromomethyl)-3-(3-fluorophenyl)prop-2-enoate
• CAS: 1609257-70-6
• 化学式: C₁₁H₁₀BrFO₂
• 分子量: 273.102
• InChiKey: JHPGOAUXLKZDGR-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-(3-fluorophenyl)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-(3-fluorophenyl)-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：

  3-氟苯甲醛 在 三乙烯二胺 、 氢溴酸 、 溶剂黄146 作用下， 反应 7.0h， 生成 (Z)-methyl 2-(bromomethyl)-3-(3-fluorophenyl)acrylate
  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

文献信息

• Microwave-assisted facile synthesis of [a]-annelated pyrazolopyrroloindoles via intramolecular azomethine imine 1,3-dipolar cycloaddition
  作者：Anand H. Shinde、Shinde Vidyacharan、Duddu S. Sharada

  DOI：10.1016/j.tetlet.2014.03.134

  日期：2014.5

  The synthesis of [a]-annelated pyrazolopyrroloindoles via intramolecular 1,3-dipolar cycloaddition of in situ generated azomethine imine from N-allylated indole-2-carboxaldehyde, in regio- and stereoselective manner by using microwave irradiation is described. A one-pot strategy for the expedient synthesis of pyrazolopyrroloindoles has been developed.

  描述了通过微波辐射以区域和立体选择性的方式通过N-烯丙基化的吲哚-2-羧醛通过原位产生的偶氮甲亚胺的分子内1,3-偶极环加成反应合成[ a ]退火的吡唑并吡咯并吲哚。已经开发了一种方便合成吡唑并吡咯并吲哚的一锅策略。