β‐acetamido‐β‐(2‐hydroxyphenyl)propiophenone | 571169-61-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: β‐acetamido‐β‐(2‐hydroxyphenyl)propiophenone
• 英文别名: β-acetamido-β-(2-hydroxyphenyl)propiophenone；Acetamide, N-[1-(2-hydroxyphenyl)-3-oxo-3-phenylpropyl]-；N-[1-(2-hydroxyphenyl)-3-oxo-3-phenylpropyl]acetamide
• CAS: 571169-61-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: GMPGTJMYIIJPCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲基苄醇 、 苯乙酮 、 乙腈 在 dodecatungstosilic acid 、 乙酰氯 作用下， 反应 1.33h， 以90%的产率得到β‐acetamido‐β‐(2‐hydroxyphenyl)propiophenone
  参考文献：
  名称：

  Heteropoly acids as solid green Brønsted acids for a one-pot synthesis of β-acetamido ketones by Dakin–West reaction

  摘要：

  An efficient improved procedure for the synthesis of beta-acetamido ketones has been developed by a heteropoly acid (HPA) catalyzed three-component coupling protocol. The present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and mild conditions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.080

文献信息

• Recyclable Magnetic Copper Ferrite Nanoparticle Catalyzed One-pot Four-component Dakin-West Reaction: Efficient Synthesis of β-Acetamido Ketones
  作者：Hamid Saeidian、Zahra Eraghi、Hamed Naseri、Saleh Vahdati Khajeh、Leila Ahmadi

  DOI：10.2174/1570178614666170726124823

  日期：2018.6.13

  CuFe2O4 nanoparticles were prepared by co-precipitation method. After the characterization of nanoparticles by XRD, SEM, EDS and TEM, their catalyst activity was investigated in the synthesis of β-acetamido ketones. CuFe2O4 nanoparticles were introduced as a recyclable, inexpensive and nontoxic catalyst in a four-component reaction of aromatic aldehydes, enolizable aromatic ketones, acetyl chloride

  采用共沉淀法制备了CuFe2O4纳米粒子。通过XRD，SEM，EDS和TEM对纳米粒子进行表征，研究了其在β-乙酰氨基酮合成中的催化活性。在室温下，将CuFe2O4纳米颗粒作为可回收，廉价且无毒的催化剂引入芳族醛，可烯化的芳族酮，乙酰氯和乙腈的四组分反应中。
• One-Pot Four-Component Dakin-West Synthesis of β-Acetamido Ketones Catalyzed by a Vanadium-Substituted Heteropolyacid
  作者：Reza TAYEBEE、Shima TIZABI

  DOI：10.1016/s1872-2067(11)60379-3

  日期：2012.4

  enolizable ketone as one-pot synthesis of β-acetamido ketones in high yields was investigated using commercial, non-corrosive, and environmentally benign Keggin and Wells-Dawson heteropolyacid catalysts. The best catalyst was H5PW10V2O40. The methodology used simple experimental conditions, and the short reaction times and high yields indicate it is a useful strategy for the large scale synthesis of β-acetamido

  使用商业、无腐蚀性和环境友好的 Keggin 和 Wells-Dawson 杂多酸催化剂，研究了芳醛、乙酰氯、乙腈和可烯醇化酮的多​​组分缩合反应，以高产率一锅法合成 β-乙酰胺酮。最好的催化剂是H5PW10V2O40。该方法使用简单的实验条件，反应时间短，收率高，表明它是大规模合成β-乙酰氨基酮的有用策略。
• Studying catalytic activity of ternary mixed‐metal Keggin H₇SiV₃W₉O₄₀as a versatile acid catalyst for the synthesis of β‐acetamido ketones
  作者：Reza Tayebee、Akbar Pejhan

  DOI：10.1002/aoc.5350

  日期：2020.2

  One‐pot four‐component condensation of an aromatic aldehyde with an enolisable ketone and acetyl chloride is investigated in the presence of H7SiV3W9O40 in acetonitrile. The prepared catalyst was characterized by standard techniques such as XRD, SEM, and FT‐IR to verify the Keggin structure of nanocatalyst. Furthermore, findings revealed a very good catalytic activity for the applied vanadium substituted

  在乙腈中存在H 7 SiV 3 W 9 O 40的情况下，研究了芳香醛与可缩合的酮和乙酰氯的单锅四组分缩合反应。用XRD，SEM和FT-IR等标准技术对制备的催化剂进行表征，以验证纳米催化剂的Keggin结构。此外，发现表明在该酸催化的缩合反应中，所用的钒取代的杂多酸具有非常好的催化活性。比较了一系列Keggin Si和V-取代的杂多酸对β-乙酰氨基-β-（4-氯苯基）苯乙酮的合成，显示出对H 7 SiV 3 W 9 O更好的催化活性。40和H 4 SiW 12 O 40比介电和混合金属Keggin H 4 SiW 9 Mo 3 O 40和H 5 SiW 9 Mo 2 VO 40高。另外，在该催化体系中也证明了硝化剂的作用，并且发现表明与乙腈相比，PhCN的熟练程度较低。此外，丙苯酮作为一种可被α-取代的可酮化酮与一些芳族醛反应，并且检测到反异构体是主要的非对映异构体。因此，H 7 SiV
• Efficient Synthesis of β‐Acetylamino Ketones using Silica‐Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst
  作者：N. Vijaya Kumari、Lingaiah Nagarapu、Shivaraj

  DOI：10.1080/00397910701410467

  日期：2007.7

  Abstract Silica‐supported sodium hydrogen sulfate (NaHSO4 · SiO2) efficiently catalyzes the four‐component reaction of aryl aldehydes, enolisable ketones, acetyl chloride, and acetonitrile to form the corresponding β‐acetylamino ketones at room temperature. The catalyst is inexpensive and ecofriendly and works under heterogeneous conditions.The present methodology offers several advantages such as

  摘要 二氧化硅负载的硫酸氢钠 (NaHSO4·SiO2) 在室温下可有效催化芳醛、可烯化酮、乙酰氯和乙腈的四组分反应生成相应的 β-乙酰氨基酮。该催化剂价格低廉且环保，可在非均相条件下工作。本方法提供了几个优点，如产率高、程序简单、反应时间短（1-3 小时）和条件温和。
• Synergic effect of nano-catalyst and continuous flow system: Dakin–West reaction catalyzed by Nafion-H@SPIONs in a microreactor
  作者：Zahra Arabloo Narei、Behnaz Shafiee、Ahmad R. Khosropour

  DOI：10.1039/c4ra15466e

  日期：——

  The expansion of practical processes for superferromagnetic nanocatalysts is a very attractive subject.

  超铁磁纳米催化剂实用化过程的拓展是一个非常有吸引力的课题。