3'-bromo-2'-hydroxy-4',6'-dimethoxy-trans-chalcone | 1159-57-5

• 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: 3'-bromo-2'-hydroxy-4',6'-dimethoxy-trans-chalcone
• 英文别名: 3'-Brom-2'-hydroxy-4',6'-dimethoxy-trans-chalkon；(E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 1159-57-5
• 化学式: C₁₇H₁₅BrO₄
• 分子量: 363.208
• InChiKey: SMCXTJBQMQBLHX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-bromo-5,7-dimethoxy-2-phenyl-chroman-4-one 在 sodium hydroxide 作用下， 生成 3'-bromo-2'-hydroxy-4',6'-dimethoxy-trans-chalcone
  参考文献：
  名称：

  Bannerjee; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1952, vol. 36, p. 134,138

  摘要：

  DOI：

文献信息

• Synthesis of chalcone analogues with increased antileishmanial activity
  作者：Paula Boeck、Camila Alves Bandeira Falcão、Paulo César Leal、Rosendo Augusto Yunes、Valdir Cechinel Filho、Eduardo Caio Torres-Santos、Bartira Rossi-Bergmann

  DOI：10.1016/j.bmc.2005.10.005

  日期：2006.3

  Eighteen analogues of an active natural chalcone were synthesized using xanhoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden. (c) 2005 Elsevier Ltd. All rights reserved.
• Regioselective monobromination of (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-aryl-2-propen-1-ones using bromodimethylsulfonium bromide and synthesis of 8-bromoflavones and 7-bromoaurones
  作者：Abu T. Khan、Abhik Choudhury、Shahzad Ali、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2012.06.122

  日期：2012.9

  A wide variety of monobrominated compounds 2a-I have been prepared in good yields from (E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-aryl-2-propen-1-ones (1a-I) through regioselective ring bromination using 1.5 equiv of bromodimethylsulfonium bromide (BDMS) at room temperature. Similarly, some of the 2'-hydroxychalcones can be converted directly into tribromides 3 or dibromides 4 by employing 4.0 equiv of BDMS under different reaction conditions which in turn can be transformed into 8-bromoflavones and 7-bromoaurones on treatment with 0.2 M ethanolic KOH solution. Mild reaction conditions, good yields and no chromatographic separation are some of the salient features of the present protocol. (C) 2012 Elsevier Ltd. All rights reserved.
• Nuclear bromination in phloroglucinol derivatives
  作者：John A. Donnelly

  DOI：10.1016/s0040-4039(01)99469-9

  日期：1959.1
• Bannerjee; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1952, vol. 36, p. 134,138
  作者：Bannerjee、Seshadri

  DOI：——

  日期：——