butyl 3-(4-formylphenyl)propanoate | 1063628-38-5

• 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: butyl 3-(4-formylphenyl)propanoate
• 英文别名: Butyl 3-(4-formylphenyl)propanoate
• CAS: 1063628-38-5
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ZGXGSASBGKOCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 4-甲酰基苯硼酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2,6-二叔丁基苯酚 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以81%的产率得到butyl 3-(4-formylphenyl)propanoate
  参考文献：
  名称：

  Ru-catalyzed 1,4-addition of arylboronic acids to acrylic acid derivatives in the presence of phenols

  摘要：

  以[Ru(p-cymene)Cl2]2为催化剂，研究了芳基硼酸与丁基丙烯酸酯和丙烯酰胺在酚类化合物存在下的1,4-加成反应，获得了良好的至优异的产率。酚的添加显著促进了质子解离，抑制了1,4-加成中间体的β-H消除，并有效抑制了芳基硼酸的质子解离。

  DOI：

  10.1039/c3cc43095b

文献信息

• Ru-catalyzed 1,4-addition of arylboronic acids to acrylic acid derivatives in the presence of phenols
  作者：Lei Zhang、Xiaomin Xie、Zhiyong Peng、Lei Fu、Zhaoguo Zhang

  DOI：10.1039/c3cc43095b

  日期：——

  [Ru(p-cymene)Cl2]2-catalyzed 1,4-addition reactions between arylboronic acids and butyl acrylate and acrylamide in the presence of phenols were investigated, good to excellent yields were obtained. The addition of phenols remarkably promoted the protonolysis and inhibited the β-H elimination of the 1,4-addition intermediates, and also efficiently suppressed the protonolysis of arylboronic acids.

  以[Ru(p-cymene)Cl2]2为催化剂，研究了芳基硼酸与丁基丙烯酸酯和丙烯酰胺在酚类化合物存在下的1,4-加成反应，获得了良好的至优异的产率。酚的添加显著促进了质子解离，抑制了1,4-加成中间体的β-H消除，并有效抑制了芳基硼酸的质子解离。
• Cobalt(II)-Catalyzed 1,4-Addition of Organoboronic Acids to Activated Alkenes: An Application to Highly<i>cis</i>-Stereoselective Synthesis of Aminoindane Carboxylic Acid Derivatives
  作者：Min-Hsien Chen、Subramaniyan Mannathan、Pao-Shun Lin、Chien-Hong Cheng

  DOI：10.1002/chem.201202575

  日期：2012.11.19

  It all adds up: The 1,4‐addition of organoboronic acids to activated alkenes catalyzed by [Co(dppe)Cl2] is described. A [3+2]‐annulation reaction of ortho‐iminoarylboronic acids with acrylates to give various aminoindane carboxylic acid derivatives with cis‐stereoselectivity is also demonstrated (see scheme; dppe=1,2‐bis(diphenylphosphino)ethane).

  所有这些加起来：描述了[Co（dppe）Cl 2 ]催化的有机硼酸与活化烯烃的1,4加成。还证明了邻亚氨基芳基硼酸与丙烯酸酯的[3 + 2]环化反应可得到具有顺式立体选择性的各种氨基茚满羧酸衍生物（见方案； dppe = 1,2-双（二苯基膦基）乙烷）。
• Air-tolerant, ligand-free nickel-catalyzed, manganese-assisted reductive Heck reaction of alkyl/aryl halides with electron-deficient olefins
  作者：Minling Xü、Lijia Qian、Gang Zou

  DOI：10.1016/j.mcat.2023.113291

  日期：2023.8

  An air-tolerant reductive Heck reaction of alkyl/aryl halides with α, β-unsaturated esters, nitriles and amides catalyzed by simple nickel bromide has been developed by using manganese as reductant in refluxing acetonitrile. Water plays a double-face role in the catalytic process, hydrolysis of the enolate and/or C-tautomer intermediates to afford the conjugate adducts while suppressing the catalysis

  以锰为还原剂，在回流乙腈中，发展了简单溴化镍催化的烷基/芳基卤化物与α 、β-不饱和酯、腈和酰胺的耐空气还原Heck反应。水在催化过程中起着双重作用，水解烯醇和/或 C-互变异构体中间体以提供共轭加合物，同时在高浓度下抑制催化作用。40 多个实例证明了镍催化锰介导过程的范围和局限性，显示出大的空间效应和良好的官能团相容性，但还原敏感的除外。
• Catalyzation of 1,4-additions of arylboronic acids to α,β-unsaturated substrates using nickel(I) complexes
  作者：Jing-Jing Meng、Min Gao、Min Dong、Yu-Ping Wei、Wen-Qin Zhang

  DOI：10.1016/j.tetlet.2014.02.046

  日期：2014.3

  Nickel(I) complexes were generated in situ from Ni (PPh3)2Cl2 using activated iron and the complexes combined with N,N′-bis(4-fluorobenzylidene) ethane-1,2-diamine (BFBED) were then used as a catalyst for the 1,4-addition reaction of arylboronic acids to α,β-unsaturated substrates. The reaction proceeded to completion and did not require the addition of a base but the addition of potassium iodide is

  使用活化铁从Ni（PPh 3）2 Cl 2原位生成镍（I）配合物，然后使用与N，N'-双（4-氟亚苄基）乙烷-1,2-二胺（BFBED）结合的配合物作为芳基硼酸与α，β-不饱和底物的1,4-加成反应的催化剂。反应进行至完全，不需要添加碱，但是添加碘化钾对于该交叉偶联反应至关重要。此外，实验观察结果表明可能存在Ni（I）–Ni（III）催化循环机制。