2-(hydroxy(4-bromophenyl)methyl)acrylic acid butyl ester | 1198113-69-7

• 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: 2-(hydroxy(4-bromophenyl)methyl)acrylic acid butyl ester
• 英文别名: butyl 2-((4-bromophenyl)(hydroxy)methyl)acrylate；Butyl 2-[(4-bromophenyl)-hydroxymethyl]prop-2-enoate
• CAS: 1198113-69-7
• 化学式: C₁₄H₁₇BrO₃
• 分子量: 313.191
• InChiKey: YTFMDYVQOLYYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxy(4-bromophenyl)methyl)acrylic acid butyl ester 、 sodium benzenesulfonate 在 copper dichloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以87%的产率得到butyl 2-benzyl-3-(4-bromophenyl)-3-oxopropanoate
  参考文献：
  名称：

  Regioselective Palladium(II)-Catalyzed Desulfitative Heck-Type Reaction: Access to α-Benzyl-β-keto Esters from Baylis-Hillman Adducts and Sodium Sulfinates

  摘要：

  A new palladium(II)-catalyzed desulfitative Heck-Type arylation from sodium arenesulfinates and Baylis-Hillman adducts for the synthesis of highly functionalized alpha-benzyl-beta-keto ester derivatives in good to excellent yields has been developed. This methodology is simple and mild, it can utilize halogen bearing building blocks, and it has excellent regioselectivity.

  DOI：

  10.1055/s-0033-1339663
• 作为产物：
  描述：

  丙烯酸丁酯 、 对溴苯甲醛 在 三乙烯二胺 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以87%的产率得到2-(hydroxy(4-bromophenyl)methyl)acrylic acid butyl ester
  参考文献：
  名称：

  Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O

  摘要：

  A recyclable protic-ionic-liquid solvent-catalyst system, DABCO-AcOH-H2O, has been developed and used in the Baylis-Hillman reaction of aromatic aldehydes, aliphatic aldehydes, and cinnamaldehydes with acrylates and acrylonitrile, showing comparable performance to free DABCO in traditional solvents. The DABCO-AcOH-H2O solvent-catalyst system could be reused for at least five times without significant loss of activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.049

文献信息

• Ligated Regioselective PdII Catalysis to Access β-Aryl-Bearing Aldehydes, Ketones, and β-Keto Esters
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1002/ejoc.201200770

  日期：2012.9

  arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′-alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis–Hillman adducts). A practical

  通过在 PdII 介导的烯丙醇芳基化异构化中使用配体，开发了一种更温和和区域选择性的通用构建块 β-芳基醛和酮。这种新的螯合控制方案使广泛的功能兼容，以生成二氢查耳酮、α-苄基-α'-烷基丙酮、二氢肉桂醛和 α-苄基 β-酮酯（来自 Baylis-Hillman 加合物）。还展示了普罗帕酮中间体的实用多克合成。
• Replacing a stoichiometric silver oxidant with air: ligated Pd(<scp>ii</scp>)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1039/c3gc42504e

  日期：——

  Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(ii)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important β-aryl carbonyl derivatives.

  空气被用作Pd（0）的绿色氧化剂，取代了化学计量且有毒的银盐，在以螯合控制的Pd（II）调控下进行的烯醇化反应中，将丙烯-1-醇芳基化，以获得具有合成重要性的β-芳基酮衍生物。
• Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O
  作者：Ying Song、Haihua Ke、Nan Wang、Limin Wang、Gang Zou

  DOI：10.1016/j.tet.2009.09.049

  日期：2009.11

  A recyclable protic-ionic-liquid solvent-catalyst system, DABCO-AcOH-H2O, has been developed and used in the Baylis-Hillman reaction of aromatic aldehydes, aliphatic aldehydes, and cinnamaldehydes with acrylates and acrylonitrile, showing comparable performance to free DABCO in traditional solvents. The DABCO-AcOH-H2O solvent-catalyst system could be reused for at least five times without significant loss of activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselective Palladium(II)-Catalyzed Desulfitative Heck-Type Reaction: Access to α-Benzyl-β-keto Esters from Baylis-Hillman Adducts and Sodium Sulfinates
  作者：Kommu Nagaiah、Kammari Bal Raju、Vellakkaran Mari

  DOI：10.1055/s-0033-1339663

  日期：——

  A new palladium(II)-catalyzed desulfitative Heck-Type arylation from sodium arenesulfinates and Baylis-Hillman adducts for the synthesis of highly functionalized alpha-benzyl-beta-keto ester derivatives in good to excellent yields has been developed. This methodology is simple and mild, it can utilize halogen bearing building blocks, and it has excellent regioselectivity.