2,2-dimethyl-3-oxo-3-(p-methoxyphenyl)propanal | 10326-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-3-oxo-3-(p-methoxyphenyl)propanal
• 英文别名: α-p-Anisoyl-isobutyraldehyd；3-(4-Methoxyphenyl)-2,2-dimethyl-3-oxopropanal
• CAS: 10326-94-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: AGNXWAHNAGXPME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-oxo-3-(p-methoxyphenyl)propanal 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 p-甲氧基异苯丁酮
  参考文献：
  名称：

  Preparation of .beta.-oxo aldehydes by acylation of aldehyde enamines

  摘要：

  DOI：

  10.1021/jo01288a032
• 作为产物：
  描述：

  4-(2-甲基丙-1-烯基)吗啉 、 对甲氧基苯甲酰氯 生成 2,2-dimethyl-3-oxo-3-(p-methoxyphenyl)propanal
  参考文献：
  名称：

  Preparation of .beta.-oxo aldehydes by acylation of aldehyde enamines

  摘要：

  DOI：

  10.1021/jo01288a032

文献信息

• 1,4-Carbonyl participation in solvolysis of alkyl toluene-p-sulphonates
  作者：Philip K. G. Hodgson、Stuart Warren

  DOI：10.1039/p29750000372

  日期：——

  2,2-Dimethyl-3-oxo-3-phenylpropyl toluene-p-sulphonate (tosylate) and some related 3-oxoalkyl tosylates are solvolysed in buffered carboxylic acid solvents by 1,4-carbonyl participation to give unrearranged carboxylate esters. The reactions are too fast to be direct displacements, and do not occur in similar compounds which lack the carbonyl group. Secondary alkyl tosylates in the same series also

  2，2-二甲基-3-氧代-3-苯基丙基甲苯对磺酸酯（甲苯磺酸酯）和一些相关的3-氧代烷基甲苯磺酸酯通过1，4-羰基参与溶剂化在缓冲的羧酸溶剂中，得到未重排的羧酸酯。该反应太快而不能直接取代，并且在缺少羰基的类似化合物中不会发生。同一系列的仲烷基甲苯磺酸盐也通过1,4-羰基参与反应，但发生中间阳离子片段，并与溶剂反应生成未重排的产物。
• Selective Aldehyde Reduction in Ketoaldehydes with NaBH₄-Na₂CO₃-H₂O at Room Temperatures
  作者：Sosale Chandrasekhar、Annadka Shrinidhi

  DOI：10.1080/00397911.2014.888751

  日期：2014.7.18

  A variety of aliphatic and aromatic ketoaldehydes were reduced to the corresponding ketoalcohols with a mixture of sodium borohydride (1.2 equivalents) and sodium carbonate (sixfold molar excess) in water. Reactions were performed at room temperatures over (typically) 2 h, and yields of isolated products generally ranged from 70% to 85%. A biscarbonate-borane complex, [(BH3)(2)CO2](2-) 2Na(+), possibly formed from the reagent mixture, is likely the active reductant. The moderated reactivity of this acylborane species would explain the chemoselectivity observed in the reactions. The readily available reagents and the mild aqueous conditions make for ease of operation and environmental compatibility, and make a useful addition to available methodology.
• The Intramolecular Aldol Condensation Route to Fused Bi- and Tricyclic β-Lactams¹^,²
  作者：Benito Alcaide、Concepción Polanco、Elena Sáez、Miguel A. Sierra

  DOI：10.1021/jo960904w

  日期：1996.1.1

  Staudinger cycloaddition of activated acid chlorides to 1,3-ketoaldimines, prepared in quantitative yields from 1,3-ketoaldehydes and amino esters, gave in excellent yields cis-a-azetidinones, 6-8, having the adequate functionality to obtain fused bi- and tricyclic beta-lactams. Reaction of compounds 6 with LHMDS at low temperature gave a single diastereomer of fused bicyclic compounds with a carbapenam or carbacefam skeleton. Treatment of diastereomeric cis-2-azetidinones, 7/8, in analogous conditions resulted either in the exclusive cyclization of one of the two diastereomers to form tricyclic [4.n.m] (n = 5, 6; m = 5, 6) compounds, or in the cyclization of both diastereomers to form tricyclic [4.n.7] (n = 5, 6) 2-azetidinones. In all cases the cyclization step was totally stereoselective. Alternatively, trans-carbapenams and one example of a tricyclic system having a trans-2-azetidinone ring have been obtained by using longer reaction times and higher temperatures. Epimerization at C3 of the 2-azetidinone nucleus occurs in these reaction conditions to obtain a single diastereomer of the final products. This approach to fused policyclic 2-azetidinones is one of the scarce syntheses of this kind of compound making use of the aldol condensation.