2'-acetoxy-4,4',6'-trimethoxychalcone | 51254-82-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-acetoxy-4,4',6'-trimethoxychalcone
• 英文别名: 2'-Acetoxy-4,4',6'-trimethoxy-chalkon；2'-Acetoxy-4',6',4-trimethoxychalkon；[3,5-dimethoxy-2-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl] acetate
• CAS: 51254-82-1
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: GPWYAMAFBGDVII-JXMROGBWSA-N

物化性质

• 沸点：
  538.4±50.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-acetoxy-4,4',6'-trimethoxychalcone 在 氢氧化钾 、 水 、 tetra-N-butylammonium tribromide 、 calcium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide

  摘要：

  A wide variety of aurones (3a-f) can be prepared exclusively from 2'-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5 degreesC followed by cyclization of the brominated. products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5 degreesC, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01938-4
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-(4-甲氧基苯基)-2-丙烯-1-酮 、 乙酰氯 以 吡啶 、 ice-water 、 氯仿 为溶剂， 以92%的产率得到2'-acetoxy-4,4',6'-trimethoxychalcone
  参考文献：
  名称：

  Substituted acetophenones and compositions containing them

  摘要：

  式##STR1##中的抗病毒活性化合物，其中R.sup.1代表羟基，来自具有2-18个碳原子的脂肪酸或含氮原子的杂环羧酸的酰氧基，较低的烷氧羰氧基，氨基酰氧基或羧基烷酰氧基；R.sup.2代表较低的烷氧基；R.sup.3代表氢或较低的烷氧基；R.sup.4代表苯基，可以被来自由下列成员的一个或多个取代基所取代：较低的烷基，较低的烷氧基，苄氧基，烯丙氧基，烷基硫醚，二烷基氨基，氨基，氰基，羟基，卤素和烷基二氧基；或吡啶基，呋喃基，噻吩基或吡咯基，可以被较低的烷基取代，其中包含它们的药物组成物以及一种制备那些新颖的式I化合物的过程。

  公开号：

  US04605674A1

文献信息

• A highly efficient and environmentally benign synthesis of 6,8-dibromoflavones, 8-bromoflavones, 5,7-dibromoaurones and 7-bromoaurones
  作者：Abu T. Khan、Papori Goswami

  DOI：10.1016/j.tetlet.2005.05.102

  日期：2005.7

  Various ring substituted 6,8-dibromoflavones (3a-e) as well as 8-bromoflavolics (3f-j) can be synthesized easily from the corresponding 2'-hydroxychalcones (1a-j) in good yields and in two steps under environmentally benign reaction conditions. This can be achieved by bromination with concomitant cyclization by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in dichloromethane-water at 0-5 degrees C, followed by dehydrobromination of the brominated products 2a-j using 0.2 M ethanolic KOH Solution at ice-bath temperature. On the other hand, various 5,7-dibromoaurones and 7-bromoaurone derivatives 6a-c can be obtained, exclusively, from the corresponding 2'-acetoxychalcones (4a-c) in good yields and in two steps by turing the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• US4605674A
  申请人：——

  公开号：US4605674A

  公开（公告）日：1986-08-12
• An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide
  作者：Gopal Bose、Ejabul Mondal、Abu T Khan、Manob J Bordoloi

  DOI：10.1016/s0040-4039(01)01938-4

  日期：2001.12

  A wide variety of aurones (3a-f) can be prepared exclusively from 2'-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5 degreesC followed by cyclization of the brominated. products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5 degreesC, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Substituted acetophenones and compositions containing them
  申请人：Hoffmann-La Roche Inc.

  公开号：US04605674A1

  公开（公告）日：1986-08-12

  Antivirally active compounds of the formula ##STR1## wherein R.sup.1 represents hydroxy, acyloxy derived from an aliphatic acid having 2-18 carbon atoms or a heterocyclic carboxylic acid containing nitrogen atom(s), lower alkoxycarbonyloxy, aminoacyloxy or carboxyalkanoyloxy; R.sup.2 represents lower alkoxy; R.sup.3 represents hydrogen or lower alkoxy; and R.sup.4 represents phenyl which may be substituted by one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, benzyloxy, allyloxy, alkylthio, dialkylamino, amino, cyano, hydroxy, halo and alkylenedioxy; or pyridyl, furyl, thienyl or pyrrolyl which may be substituted by lower alkyl, pharmaceutical compositions containing them and a process for the preparation of those compounds of formula I which are novel.

  式##STR1##中的抗病毒活性化合物，其中R.sup.1代表羟基，来自具有2-18个碳原子的脂肪酸或含氮原子的杂环羧酸的酰氧基，较低的烷氧羰氧基，氨基酰氧基或羧基烷酰氧基；R.sup.2代表较低的烷氧基；R.sup.3代表氢或较低的烷氧基；R.sup.4代表苯基，可以被来自由下列成员的一个或多个取代基所取代：较低的烷基，较低的烷氧基，苄氧基，烯丙氧基，烷基硫醚，二烷基氨基，氨基，氰基，羟基，卤素和烷基二氧基；或吡啶基，呋喃基，噻吩基或吡咯基，可以被较低的烷基取代，其中包含它们的药物组成物以及一种制备那些新颖的式I化合物的过程。