acetic acid 3-hydroxy-4-(3-phenylacryloyl)phenyl ester | 1040406-67-4

• 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: acetic acid 3-hydroxy-4-(3-phenylacryloyl)phenyl ester
• 英文别名: 2'-hydroxy-4'-acetoxychalcone；[3-hydroxy-4-[(E)-3-phenylprop-2-enoyl]phenyl] acetate
• CAS: 1040406-67-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: RECTUXYEXUIOKT-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 3-hydroxy-4-(3-phenylacryloyl)phenyl ester 、 2,3-二甲基-1,3-丁二烯 在 silver nanoparticles on silica 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以93%的产率得到
  参考文献：
  名称：

  Silver Nanoparticle-Catalyzed Diels−Alder Cycloadditions of 2′-Hydroxychalcones

  摘要：

  Metal nanoparticles are currently being employed as catalysts for a number of classical chemical transformations. In contrast, identification of novel reactions of nanoparticles, especially toward the synthesis of complex natural products and derivatives, is highly underdeveloped and represents a bourgeoning area in chemical synthesis. Herein, we report silica-supported silver nanoparticles as solid, recyclable catalysts for Diels-Alder cycloadditions of 2'-hydroxychalcones and dienes in high yield and turnover number. The use of silver nanoparticle catalysts is further demonstrated by the total synthesis of the cytotoxic natural product panduratin A employing a highly electron-rich dienophile and Lewis acid sensitive diene.

  DOI：

  10.1021/ja102482b
• 作为产物：
  描述：

  2',4'-diacetoxychalcone 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以88%的产率得到acetic acid 3-hydroxy-4-(3-phenylacryloyl)phenyl ester
  参考文献：
  名称：

  BF3·OEt2 mediated regioselective deacetylation of polyacetoxyacetophenones and its application in the synthesis of natural products

  摘要：

  We have developed an efficient method to regioselectively deacetylate polyacetoxyacetophenones using BF(3)center dot OEt(2) in excellent yields and demonstrated the application of the procedure in the synthesis of natural products. (C) 2008 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.020