3,3-bis-(4-methoxy-phenyl)-butan-2-one | 22927-05-5

• 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: 3,3-bis-(4-methoxy-phenyl)-butan-2-one
• 英文别名: 3,3-Bis-(4-methoxy-phenyl)-butan-2-on；3,3-Bis(4-methoxyphenyl)butan-2-one
• CAS: 22927-05-5
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: FPKVRENXFSRMAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-bis-(4-methoxy-phenyl)-butan-2-one 、 乙醇 生成 3,3-bis(4-methoxyphenyl)butan-2-ol
  参考文献：
  名称：

  OGATA Y.; KAWASAKI A.; HABA M.; TSUJINO T., J. ORG. CHEM. , 1977, 42, NO 14, 2423-2425

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-bis(trimethylsiloxy)-2,3-bis(4'-methoxyphenyl)butane 在 cation-radical orange 9,10-dimethoxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene*BF₄^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 0.2h， 以98%的产率得到3,3-bis-(4-methoxy-phenyl)-butan-2-one
  参考文献：
  名称：

  Acid Catalysis vs. Electron-Transfer Catalysis via Organic Cations or Cation-Radicals as the Reactive Intermediate. Are These Distinctive Mechanisms?

  摘要：

  Proton transfer to aromatic and olefinic donors (D) lends to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide.-pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions, However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of sepal ate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories.

  DOI：

  10.3891/acta.chem.scand.52-0114

文献信息

• Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline
  作者：Hui Shi、Chuan Du、Xinhang Zhang、Fukai Xie、Xiaoyu Wang、Shanshan Cui、Xiaoshi Peng、Maosheng Cheng、Bin Lin、Yongxiang Liu

  DOI：10.1021/acs.joc.7b02587

  日期：2018.2.2

  A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations

  研究了N-氟苯磺酰亚胺和FeCl 3 ·6H 2 O的催化作用，对微波加热的氢安息香素底物进行了无溶剂的频哪醇重排反应。首先通过密度泛函理论（DFT）计算研究了其选择性。然后，通过合成一系列基于DFT计算提供的见解而设计的底物，来检查官能团的耐受性。该方法的应用通过有效的一锅合成（±）-latifine和（±）-cherylline进行了证明，它们都是从芳基马鞭草科植物中分离出来的4-芳基四氢异喹啉生物碱。
• Photochemische Reaktionen. 53. Mitteilung [1]. Photochemische Addition von Alkylaromaten an Aryl-Carbonylverbindungen
  作者：D. Bellu?、K. Schaffner

  DOI：10.1002/hlca.19690520415

  日期：——

  In the preceding paper [1] a novel primary photochemical process of triplet excited α,β-conjugated cycloalkenones in toluene solution has been reported: the abstraction of a benzylic hydrogen from the solvent by the β-carbon (cf. 1 2 + 3 + 4). The reaction has been attributed to the π,π* triplet.

  在先前的论文[1]中，已经报道了三重激发的α，β-共轭环烯酮在甲苯溶液中的新的初级光化学过程：β-碳从溶剂中提取苄基氢（参见1 2 + 3 + 4）。该反应已归因于π，π*三重态。
• Destabilized Carbocations Caged in Water Microdroplets: Isolation and Real-Time Detection of <i>α-</i>Carbonyl Cation Intermediates
  作者：Anubhav Kumar、Supratim Mondal、Sandeep、Paloth Venugopalan、Anil Kumar、Shibdas Banerjee

  DOI：10.1021/jacs.1c12644

  日期：2022.3.2

  proposals of α-carbonyl cation intermediates have been driven by chemical intuition and indirect evidence. Recently, wide interest in α-carbonyl cation chemistry has opened new gates to prepare α-functionalized carbonyl compounds. Though these intrinsically unstable carbocations are formed under forcing conditions (e.g., in a strong acid medium), their fleeting existence prohibits direct observation

  在过去的 50 年中，α-羰基阳离子中间体的提议一直受到化学直觉和间接证据的推动。最近，对α-羰基阳离子化学的广泛兴趣为制备α-官能化羰基化合物打开了新的大门。尽管这些本质上不稳定的碳正离子是在强迫条件下（例如，在强酸介质中）形成的，但它们的短暂存在阻碍了直接观察或光谱测量。我们报告说，高速水性微滴在用相应的反应等分试样轰击时，可以直接从各种反应（弗里德尔-克拉夫茨芳基化、脱氧和叠氮化）中捕获 α-羰基阳离子中间体。然后将笼罩在水滴中的 α-羰基阳离子解吸到气相中，从而通过质谱法成功测量。
• SiCl4–Zn induced reductive coupling of carbonyl compounds: novel and efficient routes for one-pot syntheses of 1,2,3-triaryl-2-propen-1-ones and pinacolones at room temperature
  作者：Tarek A. Salama、Saad S. Elmorsy、Abdel-Galel M. Khalil

  DOI：10.1016/j.tetlet.2007.04.092

  日期：2007.6

  An unprecedented one-pot reductive trimerization of aromatic aldehydes to 1,2,3-triaryl-2-propen-1-ones as well as tandem reductive coupling-rearrangements of aryl ketones to pinacolone analogues was efficiently achieved using tetrachlorosilane-zinc at room temperature. (c) 2007 Elsevier Ltd. All rights reserved.
• The Pinacols and Pinacolone from p-Methoxyacetophenone
  作者：Charles C. Price、George P. Mueller

  DOI：10.1021/ja01232a039

  日期：1944.4