2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl acetate | 55210-75-8

• 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-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl acetate
• 英文别名: 2-acetoxychalcone；2-(Acetyl)oxybenzylidene acetophenone；[2-[(E)-3-oxo-3-phenylprop-1-enyl]phenyl] acetate
• CAS: 55210-75-8
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: TUMBTXSGFTVGFD-VAWYXSNFSA-N

物化性质

• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl acetate 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 48.25h， 生成 2-Benzoyl-5,7-dibrombenzofuran
  参考文献：
  名称：

  Reaction of Chalcones with NBS, a Simple One Pot Synthesis of 2-Aroylbenzo[b]furanes

  摘要：

  A simple one pot synthesis of 2-aroylbenzo[b]furanes has been achieved by bromomethoxylation with NBS and subsequent treatment of the appropriately substituted 2-hydroxychalcones with sodium hydroxide.

  DOI：

  10.1080/00397919608004609
• 作为产物：
  描述：

  苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 49.0h， 生成 2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl acetate
  参考文献：
  名称：

  Ortho effect in the fragmentation of 2-acetoxychalcones under electron impact

  摘要：

  Abstract2‐Acetoxychalcones decompose under electron impact conditions by loss of an acetoxy fragment to form flavylium ions. The effect is restricted to the ortho position and is reduced after hydrogenation of the chalcone double bond. The intense flavylium ion originates—as shown by specific labelling with 18O—from two different fragmentation lines: (a) direct loss of an acetoxy radical by cleavage of the phenolic ArO bond and (b) sequential elimination of ketene and a hydroxy radical.

  DOI：

  10.1002/oms.1210190708

文献信息

• Preparation of functional benzofurans and indoles via chemoselective intramolecular Wittig reactions
  作者：Yu-Ting Lee、Yeong-Jiunn Jang、Siang-en Syu、Shu-Chi Chou、Chia-Jui Lee、Wenwei Lin

  DOI：10.1039/c2cc33972b

  日期：——

  A general preparation of new types of benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester and amide functionalities using in situ formed phosphorus ylides as key intermediates. The reaction conditions are very mild, and numerous Michael acceptors and commercially available acid chlorides can be applied very

  新型苯并呋喃，苯并噻吩和吲哚的一般制备方法是通过化学选择性分子内Wittig反应，使用原位形成的磷化磷作为主要中间体，与相应的酯，硫酯和酰胺官能团进行的。反应条件非常温和，可以一步一步高效地应用许多迈克尔受体和市售的酰氯。
• [EN] AMINOALKYL SUBSTITUTED CHALCONES AND ANALOGUES AND DERIVATIVES THEREOF<br/>[FR] CHALCONES SUBSTITUÉES PAR AMINOALKYLE ET ANALOGUES ET DÉRIVÉS ASSOCIÉS
  申请人：UNIV FREE STATE ZA

  公开号：WO2011151789A2

  公开（公告）日：2011-12-08

  This invention relates to B-ring aminoalkyl substituted chalcones and analogues thereof. It also relates to processes for the synthesis of such compounds and to the use of such compounds as medicaments, in particular but not exclusively for the treatment of cancer and malaria.
• Ortho effect in the fragmentation of 2-acetoxychalcones under electron impact
  作者：Rolf Mentlein、Erich Vowinkel

  DOI：10.1002/oms.1210190708

  日期：1984.7

  Abstract2‐Acetoxychalcones decompose under electron impact conditions by loss of an acetoxy fragment to form flavylium ions. The effect is restricted to the ortho position and is reduced after hydrogenation of the chalcone double bond. The intense flavylium ion originates—as shown by specific labelling with 18O—from two different fragmentation lines: (a) direct loss of an acetoxy radical by cleavage of the phenolic ArO bond and (b) sequential elimination of ketene and a hydroxy radical.
• Reaction of Chalcones with NBS, a Simple One Pot Synthesis of 2-Aroylbenzo[b]furanes
  作者：György Litkei、Katalin Gulácsi、Sándor Antus、Zoltán Dinya

  DOI：10.1080/00397919608004609

  日期：1996.8

  A simple one pot synthesis of 2-aroylbenzo[b]furanes has been achieved by bromomethoxylation with NBS and subsequent treatment of the appropriately substituted 2-hydroxychalcones with sodium hydroxide.