2'-Benzyloxychalcon | 31487-82-8

• 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'-Benzyloxychalcon
• 英文别名: 3-[2-(Benzyloxy)phenyl]-1-phenylprop-2-en-1-one；(E)-1-phenyl-3-(2-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 31487-82-8
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: CBDLLBDTLMYFRZ-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-Benzyloxychalcon 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到2-hydroxychalcone
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).

  DOI：

  10.3109/14756366.2010.543420
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 生成 2'-Benzyloxychalcon
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).

  DOI：

  10.3109/14756366.2010.543420

文献信息

• Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5-Diaryl-hexahydropyrano[3,4-<i>c</i>]chromene Skeleton of Calyxins I and J
  作者：Basi V. Subba Reddy、Mittapalli Ramana Reddy、Sama Gopal Reddy、Balasubramanyan Sridhar、Singarapu Kiran Kumar

  DOI：10.1002/ejoc.201500117

  日期：2015.5

  A Prins bicyclization strategy for the stereoselective synthesis of trans-fused hexahydropyrano[3,4-c]chromene derivatives in good to excellent yields has been developed. The synthetic versatility of this approach has been demonstrated in the synthesis of calyxin I and J analogues. This is the first example of the synthesis of hexahydropyrano[3,4-c]chromene derivatives from (E)-3-[2-(benzyloxy)phe

  已经开发了一种用于立体选择性合成反式稠合六氢吡喃并 [3,4-c] 色烯衍生物的 Prins 双环化策略，收率很好。这种方法的合成多功能性已在花萼 I 和 J 类似物的合成中得到证明。这是从 (E)-3-[2-(苄氧基)苯基]-5-苯基戊-4-en-1-醇 (4b) 和醛类。
• Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
  作者：Lei Ma、Zhengyi Yang、Chenjing Li、Zhiyuan Zhu、Xu Shen、Lihong Hu

  DOI：10.3109/14756366.2010.543420

  日期：2011.10.1

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).