1,1-dimethoxy-3-phenyl-2-propanone | 77252-94-9

• 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: 1,1-dimethoxy-3-phenyl-2-propanone
• 英文别名: 3-phenyl methylglyoxal dimethyl acetal；3,3-dimethoxy-1-phenylpropan-2-one；1,1-dimethoxy-3-phenylpropan-2-one
• CAS: 77252-94-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: DPRDIGNALAKBDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-3-phenyl-2-propanone 在 对甲苯磺酸 水 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 2-氧代-3-苯基-丙醛
  参考文献：
  名称：

  Selenium-mediated conversion of alkynes into .alpha.-dicarbonyl compounds

  摘要：

  The reaction of terminal and internal alkynes with diphenyl diselenide and ammonium peroxydisulfate in methanol proceeds smoothly to give alpha-keto acetals and alpha-keto ketals, respectively. This one-pot procedure is suggested to proceed through the initial formation of phenylselenenyl sulfate, a strong electrophilic reagent which effects the methoxyselenenylation of the alkynes. The addition products thus formed suffer methoxydeselenenylation giving the observed products and regenerating the phenylselenenylating agent. In some cases the reaction can be carried out using only catalytic amounts of diphenyl diselenide. The same reaction carried out in the presence of water or of ethylene glycol gives the unprotected or the diprotected alpha-dicarbonyl compounds, respectively.

  DOI：

  10.1021/jo00014a038
• 作为产物：
  描述：

  2-methoxy-2-(phenyl)acetyl chloride 在 盐酸 、 三氟化硼乙醚 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 58.5h， 生成 1,1-dimethoxy-3-phenyl-2-propanone
  参考文献：
  名称：

  Yu, Yin; Chen, Guo-qiang; Zhu, Jun, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2239 - 2243

  摘要：

  DOI：

文献信息

• Efficient Preparation of α-Ketoacetals
  作者：Francisco Ayala-Mata、Citlalli Barrera-Mendoza、Hugo Jiménez-Vázquez、Elena Vargas-Díaz、L. Zepeda

  DOI：10.3390/molecules171213864

  日期：——

  The Weinreb amides 2a,b were prepared from the α,α-dimethoxyacetic acids 1c,d. A number of representative nucleophilic additions (RMgX and RLi) on 2 afforded α-ketoacetals 3a–j in 70–99% yield. These compounds represent a versatile arrangement of functional groups of significant synthetic value, as demonstrated in the synthesis of (±)-salbutamol.

  Weinreb酰胺2a，b由α，α-二甲氧基乙酸1c，d制备。在2上进行多种典型的亲核加成（RMgX和RLi），以70-99%的产率得到了α-酮缩醛3a-j。这些化合物代表着具有重要合成价值的多种官能团的灵活排列，如合成（±）-沙丁胺醇所示。
• Selective Protection of the Functionalities of α-Hydroxy Unsaturated Aldehydes
  作者：L. Khamliche、S. Bakkas、A. Robert

  DOI：10.1055/s-1994-25652

  日期：——

  The polyfunctionalized title compounds α-enol aldehydes are selectively protected either as ethylenic aldehyde acetates, ethylenic aldehyde sulfonates, ethylenic acetal sulfonates, or oxo acetal derivatives.

  多官能化的标题化合物δ-烯醇醛可选择性地以乙烯醛乙酸酯、乙烯醛磺酸盐、乙烯缩醛磺酸盐或氧代缩醛衍生物的形式进行保护。
• Kinetic and mechanistic studies on the rearrangement of 1-(substituted phenyl)-1,3-dimethoxy-2-propanones
  作者：Guo-qiang Cheng、Zhi-fen Li、Pang Zhang

  DOI：10.1016/s0008-6215(00)90539-1

  日期：1991.8

  mechanism of rearrangement of 1-(substituted phenyl)-1,3-dimethoxy-2-propanones to give substituted benzylglyoxal dimethyl acetals ( 5 ) was studied by kinetic measurements, by the effects of acid catalysis, by rearangements in the absence of acid and in the presence of base, by solvent effects, by effects of temperature, and by mass spectroscopy. It is concluded that the title ketones rearrange by a sigmatropic

  摘要通过动力学测量，酸催化作用，在不存在苯甲酸的情况下进行重排，研究了1-（取代苯基）-1,3-二甲氧基-2-丙烷重排生成取代的苄基乙二醛二甲基乙缩醛（5）的机理。酸和碱的存在下，通过溶剂的作用，通过温度的影响，和通过质谱。结论是，标题酮是通过σ而不是S n 1'的烯丙基位移而重排的。
• DDQ mediated one step dimerisation of beta-asarone or beta-asarone rich acorus calamus oil in the formation of novel neolignan
  申请人：Council of Scientific & Industrial Research

  公开号：US20030187306A1

  公开（公告）日：2003-10-02

  The present invention relates to a novel neolignan (NEOLASA-I) 3-ethyl-2-methyl-3-(2″,4″,5″-trimethoxy-phenyl-1-(2′,4′,5′-trimethoxy)phenyl-1-(2′,4′,5′-trimethoxy)phenyl-1-propene and a process for the preparation of high purity, higher yield neolignan, &agr;-asarone, 2,4,5-trimethoxy-phenyl propionone from &bgr;-asarone or &bgr;-asarone rich Acorus calamus oil containing &agr; and &ggr;-asarone by hydrogenating and dimerizing by treatment with DDQ in presence of an organic acid.

  本发明涉及一种新型新木酚类化合物（NEOLASA-I），即3-乙基-2-甲基-3-（2″，4″，5″-三甲氧基苯基）-1-（2′，4′，5′-三甲氧基苯基）-1-丙烯基-1-（2′，4′，5′-三甲氧基苯基）-1-丙烯基，以及从含有α-芳草醚和β-芳草醚的Acorus calamus油中通过氢化和二聚化处理并在有机酸存在下用DDQ制备高纯度、高产率的新木酚类化合物α-芳草醚、2,4,5-三甲氧基苯基丙酮的方法。
• Process for 3,4-dimethoxyphenyl-acetone preparation
  申请人：LARK S.p.A.

  公开号：EP0247526A2

  公开（公告）日：1987-12-02

  A process for preparing 3,4-dimethoxyphenylacetone is disclosed, which consists in electrolytically epoxidating isoeugenol-methylether in a mixture consisting of water and of a dipolar aprotic solvent, in the presence of Br⁻ ions, and in isomerizing the so-obtained epoxide, in an inert organic solvent, in the presence of catalytic amounts of lithium salts, by means of a heating at temperatures comprised within the range of from 50°C up to the solvent refluxing temperatures.

  本发明公开了一种制备 3,4-二甲氧基苯基丙酮的工艺，该工艺包括在由水和二极性非烷基溶剂组成的混合物中，在硼离子的存在下，电解环氧化异丁香酚-甲基醚、并在惰性有机溶剂中，在催化量的锂盐存在下，通过在 50°C 至溶剂回流温度范围内加热的方式，使得到的环氧化物异构化。