Ethyl 3-(2-bromo-4-fluorophenyl)prop-2-enoate | 1171825-32-3

• 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: Ethyl 3-(2-bromo-4-fluorophenyl)prop-2-enoate
• CAS: 1171825-32-3
• 化学式: C₁₁H₁₀BrFO₂
• 分子量: 273.102
• InChiKey: SMUPSFNKVDBKSI-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：
  0.18
• 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：

  Ethyl 3-(2-bromo-4-fluorophenyl)prop-2-enoate 在 三氟甲磺酸 、 苄基三乙基氯化铵 、 palladium diacetate 、 potassium carbonate 、 双(2-二苯基磷苯基)醚 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 9-fluoro-11-phenyl-5H-benzo[a]fluoren-5-one
  参考文献：
  名称：

  A two-step access to fused-/spiro-polycyclic frameworks via double Heck cascade and acid-driven processes

  摘要：

  本报告展示了通过双赫克级联反应和酸驱动环化，从容易获得的前体中快速构建出两类不同的多环框架--苯并[a]芴酮和螺色酮茚。

  DOI：

  10.1039/d3ob01112g
• 作为产物：
  描述：

  2-溴-4-氟苯甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 反应 2.0h， 生成 Ethyl 3-(2-bromo-4-fluorophenyl)prop-2-enoate
  参考文献：
  名称：

  6,7-Dihydro-5H-pyrrolo[1,2-a] imidazoles as potent and selective α1A adrenoceptor partial agonists

  摘要：

  Novel pyrroloimidazoles have been identified as potent partial agonists of the alpha(1A) adrenergic receptor, with good selectivity over the alpha(1B), alpha(1D) and alpha(2A) receptor subtypes. Pyrimidine 19 possessed attractive CNS drug-like properties with good membrane permeability and no evidence for P-gp mediated efflux. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.166

文献信息

• Palladium-Catalyzed Tandem Reactions of β-(2-Bromophenyl)-α,β-Unsaturated Carbonyl Compounds with 2-Hydroxyphenylboronic Acid: A New Route to Benzo[c]chromenes
  作者：Qihua Zhu、Xuyan Wang、Yungen Xu

  DOI：10.1002/ejoc.201101670

  日期：2012.2

  Palladium-catalyzed tandem reactions of β-(2-bromophenyl)-α,β-unsaturated carbonyl compounds with 2-hydroxyphenylboronic acid for the synthesis of benzo[c]chromenes are presented. This mild reaction allows formation of onecarbon–carbon bond and one carbon–oxygen bond in one pot.

  钯催化β-(2-溴苯基)-α,β-不饱和羰基化合物与2-羟基苯基硼酸的串联反应合成苯并[c]色烯。这种温和的反应允许在一锅中形成一个碳-碳键和一个碳-氧键。
• Synthesis of 6-Substituted Phenanthridine Derivatives by Palladium-Catalysed Domino Suzuki-Miyaura/Aza-Michael Reactions
  作者：Xiaobo Bao、Wei Yao、Qihua Zhu、Yungen Xu

  DOI：10.1002/ejoc.201402913

  日期：2014.11

  An efficient method for the synthesis of 6-substituted phenanthridine derivatives has been developed through a one-pot process involving a sequence of palladium-catalysed Suzuki–Miyaura reaction followed by intramolecular aza-Michael addition. This method is applicable to the synthesis of a wide range of substituted phenanthridines from simple substrates.

  已经通过一锅法开发了一种合成 6-取代菲啶衍生物的有效方法，该方法涉及一系列钯催化的 Suzuki-Miyaura 反应，然后是分子内 aza-Michael 加成。该方法适用于从简单底物合成多种取代菲啶。
• 6,7-Dihydro-5H-pyrrolo[1,2-a] imidazoles as potent and selective α1A adrenoceptor partial agonists
  作者：Lee R. Roberts、Paul V. Fish、R. Ian Storer、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2009.03.166

  日期：2009.6

  Novel pyrroloimidazoles have been identified as potent partial agonists of the alpha(1A) adrenergic receptor, with good selectivity over the alpha(1B), alpha(1D) and alpha(2A) receptor subtypes. Pyrimidine 19 possessed attractive CNS drug-like properties with good membrane permeability and no evidence for P-gp mediated efflux. (C) 2009 Elsevier Ltd. All rights reserved.
• A two-step access to fused-/spiro-polycyclic frameworks <i>via</i> double Heck cascade and acid-driven processes
  作者：Komal Goel、Gedu Satyanarayana

  DOI：10.1039/d3ob01112g

  日期：——

  This report illustrates the rapid construction of two divergent classes of polycyclic frameworks, benzo[a]fluorenones and spiro-chromenone indenes, via a double Heck cascade and an acid-driven cyclization from easily accessible precursors.

  本报告展示了通过双赫克级联反应和酸驱动环化，从容易获得的前体中快速构建出两类不同的多环框架--苯并[a]芴酮和螺色酮茚。