3-ethoxy-1-phenyl-1-propanone | 34008-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethoxy-1-phenyl-1-propanone
• 英文别名: β-Ethoxy-propiophenon；3-ethoxy-1-phenylpropan-1-one
• CAS: 34008-71-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: AUOLHXKGWUNYJA-UHFFFAOYSA-N

物化性质

• 熔点：
  11.5°C
• 沸点：
  270.46°C (rough estimate)
• 密度：
  1.0386

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethoxy-1-phenyl-1-propanone 在 盐酸 、 三氟甲磺酸酐 、 溶剂黄146 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 104.0h， 生成 4-Ethoxy-2-hydroxy-2-phenyl-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis and muscarinic cholinergic receptor affinities of 3-quinuclidinyl .alpha.-(alkoxyalkyl)-.alpha.-aryl-.alpha.-hydroxyacetates

  摘要：

  Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By contrast, an oxygen in the gamma-position did not change the affinity for the muscarinic receptor. However, when a bromine was placed on the remaining phenyl ring, the affinity was significantly reduced in striking contrast to results obtained on halogenation of QNB.

  DOI：

  10.1021/jm00114a006
• 作为产物：
  描述：

  3-乙氧基丙酸 在 氯化亚砜 作用下， 生成 3-ethoxy-1-phenyl-1-propanone
  参考文献：
  名称：

  Synthesis of Certain 2-Alkoxyethyl Phenyl Ketones

  摘要：

  DOI：

  10.1021/ja01178a065

文献信息

• Additive‐Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
  作者：Brian Spiegelberg、Andrea Dell'Acqua、Tian Xia、Anke Spannenberg、Sergey Tin、Sandra Hinze、Johannes G. de Vries

  DOI：10.1002/chem.201901148

  日期：2019.6.12

  Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base

  通过在不存在任何添加剂的情况下使用空气和湿气稳定的钴（II）配合物，可以实现烯丙醇在乙醇中的催化异构化（绿色溶剂）。在温和的条件下，被磷原子上的苯基取代的钴PNP钳形络合物似乎是活性最高的。即使加入一当量的碱可大大提高反应速度，但在120°C时仍可获得较高的反应速率。尽管获得了支持脱氢-加氢机理的一些证据，但已证明这不是主要机理。取而代之的是，乙醇脱氢形成的氢化钴配合物能够通过烯烃插入-消除反应实现双键异构化。
• Cu-Catalyzed Sequential Dehydrogenation–Conjugate Addition for β-Functionalization of Saturated Ketones: Scope and Mechanism
  作者：Xiaoming Jie、Yaping Shang、Xiaofeng Zhang、Weiping Su

  DOI：10.1021/jacs.6b01337

  日期：2016.5.4

  The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible

  报道了第一个铜催化的饱和酮直接β-官能化。该协议使不同的酮能够在操作简单的条件下以通常良好的产率与广泛的氮、氧和碳亲核试剂结合。进行了详细的机理研究，包括动力学研究、KIE 测量、反应中间体的鉴定、EPR 和紫外可见实验，结果表明该反应是通过一种新型的基于自由基的脱氢生成烯酮和随后的共轭加成序列进行的。
• Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis
  作者：Benito Alcaide、Pedro Almendros、M. Teresa Quirós、Ramón López、María I. Menéndez、Aleksandra Sochacka-Ćwikła

  DOI：10.1021/ja3108966

  日期：2013.1.16

  Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition

  伯和仲炔丙基氢过氧化物与各种亲核试剂（包括醇、酚、2-羟基萘-1,4-二酮和吲哚）的受控金催化反应允许直接有效地合成 β-官能化酮。此外，已经证明了一些所得产物用于选择性制备稠合多环的效用。此外，还进行了密度泛函理论 (DFT) 计算和 (18) O 标记实验，以深入了解炔丙基氢过氧化物与外部亲核试剂在金催化下的受控反应性的各个方面。
• Elimination and addition reactions. Part 30. Leaving group abilities in alkene-forming eliminations activated by sulphonyl groups
  作者：Donald R. Marshall、Patsy J. Thomas、Charles J. M. Stirling

  DOI：10.1039/p29770001898

  日期：——

  Rates of elimination of the group Z from a series of β-substituted sulphones, PhSO2·CH2·CH2Z, in ethanolic sodium ethoxide at 25 °C have been measured. For each substrate, the mechanism of the reaction has been shown to be the reversible carbanion mechanism [(E1cB)R] by determination of the primary kinetic deuterium isotope effect or by demonstration that deuterium-hydrogen exchange at Cβ is very much

  在25°C的乙醇乙醇钠中，已测定了从一系列β-取代的砜PhSO 2 ·CH 2 ·CH 2 Z中消除Z基团的速率。对于每个基板，所述反应的机理已被证明是可逆碳负离子机构[（ë 1 CB）- [R ]通过测定的主动力学氘同位素效应或通过示范其中C氘-氢交换β是非常快比消除。
• Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer
  作者：Dhika Aditya Gandamana、Bin Wang、Ciputra Tejo、Benoit Bolte、Fabien Gagosz、Shunsuke Chiba

  DOI：10.1002/anie.201801953

  日期：2018.5.22

  A new protocol for the deoxygenation of alcohols and the hydrogenation of alkenes under Brønsted acid catalysis has been developed. The method is based on the use of either a benzyl or isopropyl ether as a traceless hydrogen‐atom donor, and involves an intramolecular hydride transfer as a key step, which is achieved in a regio‐ and stereoselective manner.

  已经开发了在布朗斯台德酸催化下醇的脱氧和烯烃的氢化的新方案。该方法基于使用苄基或异丙基醚作为无痕氢原子供体，并且涉及分子内氢化物转移作为关键步骤，这是通过区域和立体选择性方式实现的。