1-乙酰氧基-1-(3,4-二甲氧基-苯基)-丙酮 | 38007-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-乙酰氧基-1-(3,4-二甲氧基-苯基)-丙酮
• 英文名称: 1-acetoxy-1-(3,4-dimethoxy-phenyl)-acetone
• 英文别名: 1-Acetoxy-1-(3,4-dimethoxy-phenyl)-aceton；[1-(3,4-Dimethoxyphenyl)-2-oxopropyl] acetate
• CAS: 38007-20-4
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: LCZFFTTYSVVMBY-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±42.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-1-(3,4-二甲氧基-苯基)-丙酮 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 BF*Et₂O 、 potassium tert-butylate 、 四氯化钛 、 对甲苯磺酸 、 三乙胺 、 lithium diisopropyl amide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.25h， 生成 5'-demethoxyporosin
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae).

  摘要：

  藜芦醛与2-氯丙酸甲酯缩合得到缩水甘油酯。将其用氢氧化钠水溶液水解，并将所得钠盐用四乙酸铅(IV)处理，得到1-乙酰氧基-1-(3,4-二甲氧基苯基)丙-2-酮(13)。 13 与丙二酸二甲酯缩合，然后进行酸水解和硼氢化钠还原，得到 (2R*, 3S*, 4R*)-4-(3, 4-二甲氧基苯基)-2-甲氧基羰基-3-甲基-4-丁内酯 (7a ）。然后通过一系列反应将γ-内酯7a转化为5'-脱甲氧基孔松素(10)：与甲基乙烯基酮的迈克尔反应、消除甲氧基羰基、缩醛化、烯丙基化、脱缩醛化和分子内羟醛反应。在10的C-5'位置引入羟基，然后用重氮甲烷甲基化，得到外消旋孔松蛋白。合成的孔隙素进一步转化为5-去甲氧基扩音器乙酸酯。

  DOI：

  10.1248/cpb.43.2099
• 作为产物：
  描述：

  1-Chlor-2-oxo-3-(3,4-dimethoxyphenyl)-propan 在 吡啶 、 水 、 potassium acetate 、 甲苯 作用下， 生成 1-乙酰氧基-1-(3,4-二甲氧基-苯基)-丙酮
  参考文献：
  名称：

  Studies on Lignin and Related Compounds. LXXIV. Relation of Wood Ethanolysis Products to the Hibbert Series of Plant Respiratory Catalysts. Allylic and Dismutation Rearrangements of 3-Chloro-1-(3,4-dimethoxyphenyl)-2-propanone and 1-Bromo-1-(3,4-dimethoxyphenyl)-2-propanone

  摘要：

  DOI：

  10.1021/ja01229a009

文献信息

• DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage:  Lignin Model Studies
  作者：Fachuang Lu、John Ralph

  DOI：10.1021/jf970539p

  日期：1997.12.1

  A new method for selective and efficient cleavage of arylglycerol-beta-aryl (beta-O-4) ether linkages in lignins is described and applied to several Lignin beta-ether models. The term "DFRC" was coined for derivatization followed by reductive cleavage. Derivatization, accompanied by cell wall solubilization, is accomplished with acetyl bromide (AcBr); reductive cleavage of resulting beta-bromo ethers utilizes zinc in acetic acid. Degradation monomers, 4-acetoxycinnamyl acetates, from beta-ether cleavage by the DFRC method were identified by NMR, CC-MS, and comparison of GC retention times with authentic compounds. Under the conditions used in this study, the beta-ether linkage of all models was cleaved in very high (> 92%) yield. The DFRC method produces simpler mixtures of monomers with higher yields than alternative hydrolytic methods. Because of its relative simplicity, mild conditions, and exceptional selectivity, this method should become a powerful analytical method for lignin characterization.
• �ber die Konstitution der synthetischen und durch �thanolyse aus dem Holz isolierbaren Ketole vom Typus des Oxy-propio-guajacons
  作者：A. Wacek、I. Horak

  DOI：10.1007/bf00898991

  日期：——
• Studies on Lignin and Related Compounds. LXXIV. Relation of Wood Ethanolysis Products to the Hibbert Series of Plant Respiratory Catalysts. Allylic and Dismutation Rearrangements of 3-Chloro-1-(3,4-dimethoxyphenyl)-2-propanone and 1-Bromo-1-(3,4-dimethoxyphenyl)-2-propanone
  作者：Arthur M. Eastham、H. E. Fisher、Marshall Kulka、Harold Hibbert

  DOI：10.1021/ja01229a009

  日期：1944.1
• Total Synthesis of (.+-.)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae).
  作者：Takashi MATSUMOTO、Yoshio TAKEDA、Masaki OIWAMOTO、Kazunari FUJII、Masashi KISHIDA、Hiroshi SHIBUTANI、Sachihiko IMAI

  DOI：10.1248/cpb.43.2099

  日期：——

  Veratraldehyde was condensed with methyl 2-chloropropanoate to give a glycidic ester. This was hydrolyzed with aqueous sodium hydroxide and the resulting sodium salt was treated with lead(IV) tetraacetate to give 1-acetoxy-1-(3, 4-dimethoxyphenyl)propan-2-one (13). Condensation of 13 with dimethyl malonate, followed by acidic hydrolysis and sodium borohydride reduction afforded (2R*, 3S*, 4R*)-4-(3, 4-dimethoxyphenyl)-2-methoxycarbonyl-3-methyl-4-butanolide (7a). The γ-lactone 7a was then converted into 5'-demethoxyporosin (10) by means of a series of reactions : Michael reaction with methyl vinyl ketone, elimination of the methoxycarbonyl group, acetalization, allylation, deacetalization, and intramolecular aldol reaction. Introduction of a hydroxyl group at the C-5' position in 10, followed by methylation with diazomethane afforded racemic porosin. The synthetic porosin was further converted into 5-demethoxymegaphone acetate.

  藜芦醛与2-氯丙酸甲酯缩合得到缩水甘油酯。将其用氢氧化钠水溶液水解，并将所得钠盐用四乙酸铅(IV)处理，得到1-乙酰氧基-1-(3,4-二甲氧基苯基)丙-2-酮(13)。 13 与丙二酸二甲酯缩合，然后进行酸水解和硼氢化钠还原，得到 (2R*, 3S*, 4R*)-4-(3, 4-二甲氧基苯基)-2-甲氧基羰基-3-甲基-4-丁内酯 (7a ）。然后通过一系列反应将γ-内酯7a转化为5'-脱甲氧基孔松素(10)：与甲基乙烯基酮的迈克尔反应、消除甲氧基羰基、缩醛化、烯丙基化、脱缩醛化和分子内羟醛反应。在10的C-5'位置引入羟基，然后用重氮甲烷甲基化，得到外消旋孔松蛋白。合成的孔隙素进一步转化为5-去甲氧基扩音器乙酸酯。