n-butyl 3-(4-fluorophenyl)propanoate | 1063628-34-1

• 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: n-butyl 3-(4-fluorophenyl)propanoate
• 英文别名: butyl 3-(4-fluorophenyl)propanoate；butyl 4-fluorobenzenepropanoate；Butyl 3-(4-fluorophenyl)propanoate
• CAS: 1063628-34-1
• 化学式: C₁₃H₁₇FO₂
• 分子量: 224.275
• InChiKey: YCOBGWLASNJISV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 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-氟苯硼酸 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86%的产率得到n-butyl 3-(4-fluorophenyl)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

• 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。
• Ligand-Free Nickel-Catalysed 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds
  作者：Wen Chen、Lu Sun、Xi Huang、Jiayi Wang、Yanqing Peng、Gonghua Song

  DOI：10.1002/adsc.201400761

  日期：2015.5.4

  catalytic system has been developed for the 1,4‐addition of arylboronic acids to α,β‐unsaturated carbonyl compounds. With catalyst loadings of 1–2 mol%, a series of 1,4‐adducts from chalcones and cinnamates was obtained in moderate to excellent yields within 5–30 min under a nitrogen atmosphere and microwave irradiation. The 1,4‐addition of arylboronic acids to acrylates is less efficient.

  已开发出一种简单有效的不含配体的镍基催化体系，用于将芳基硼酸1,4-加成到α，β-不饱和羰基化合物上。当催化剂负载量为1-2 mol％时，在氮气氛和微波辐射下5-30分钟内，从查耳酮和肉桂酸盐中获得了一系列1,4-加合物。芳基硼酸与丙烯酸酯的1,4加成效率较低。
• Rhodium Fluoroapatite Catalyzed Conjugate Addition of Arylboronic Acids to<i>α</i>,<i>β</i>-Unsaturated Carbonyl Compounds
  作者：Mannepalli Lakshmi Kantam、Vura Bala Subrahmanyam、Kota Balaji Shiva Kumar、Gopaladasu T. Venkanna、Bojja Sreedhar

  DOI：10.1002/hlca.200890208

  日期：2008.10

  Rhodium fluoroapatite (RhFAP) is an efficient catalyst for conjugate addition of organoboron reagents to α,β-unsaturated carbonyl compounds. A variety of arylboronic acids and α,β-unsaturated carbonyl compounds were converted to the corresponding conjugate-addition products, demonstrating the versatility of the reaction. The reaction is highly selective. RhFAP was recovered quantitatively by simple filtration

  氟磷灰石铑（RhFAP）是一种有效的催化剂，用于将有机硼试剂共轭加成到α，β-不饱和羰基化合物上。各种芳基硼酸和α，β-不饱和羰基化合物被转化为相应的共轭加成产物，证明了该反应的多功能性。该反应是高度选择性的。通过简单过滤定量回收RhFAP，并重复使用四个周期。
• Highly Efficient and Reusable Polyaniline-Supported Palladium Catalysts for Open-Air Oxidative Heck Reactions under Base- and Ligand-Free Conditions
  作者：Pravin R. Likhar、Moumita Roy、Sarabindu Roy、M. S. Subhas、M. Lakshmi Kantam、B. Sreedhar

  DOI：10.1002/adsc.200800329

  日期：2008.9.5

  Oxidative Heck reactions of arylboronic acids and alkenes are carried out in the presence of polyaniline-supported palladium catalysts using air as a co-oxidant to afford the Heck products with excellent yields and selectivities under base- and ligand-free conditions. The catalyst was recovered by simple filtration and used for several cycles with consistent activity.

  在聚苯胺负载的钯催化剂的存在下，使用空气作为助氧化剂，进行芳基硼酸和烯烃的氧化Heck反应，从而在无碱和无配体的条件下提供具有优异收率和选择性的Heck产物。通过简单过滤回收催化剂，并以一致的活性使用数个循环。