2,6-Dibromo-4-[(3-bromo-4-hydroxyphenyl)methyl]phenol | 1009647-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-Dibromo-4-[(3-bromo-4-hydroxyphenyl)methyl]phenol
• CAS: 1009647-13-5
• 化学式: C₁₃H₉Br₃O₂
• 分子量: 436.925
• InChiKey: CAACPSHFXPZNGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4'-二羟基二苯甲烷 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-Bromo-4-[(3-bromo-4-hydroxyphenyl)methyl]phenol 、 2,6-Dibromo-4-[(3-bromo-4-hydroxyphenyl)methyl]phenol
  参考文献：
  名称：

  Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives

  摘要：

  A series of bromophenols was obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine. New bromophenols including 3,3,5,5'-tetrabromo-2,2',4,4'-tetrahydroxydiphenylmethane (10), a regioisomer of the potent antimicrobial natural product, together with known derivatives were synthesized in high yield. All of the isolated and synthesized compounds were tested for antimicrobial activity against Gram-negative, Gram-positive bacteria and fungi. The preliminary structure-activity relationship, to elucidate the essential structure requirements for antimicrobial activity, has been described. Among the isolated natural products 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane (4) was found to be the most active derivative against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. The synthetic bromophenols 3,3'-dibromo-6,6'-dihydroxydiphenylmethane (13) and 3,3',5,5'-tetrabromo-6, 6'-dihydroxydiphenylmethane (14) showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus. Proteus vulgaris, and Salmonella typhimurium. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.003

文献信息

• Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives
  作者：Ki-Bong Oh、Ji Hye Lee、Soon-Chun Chung、Jongheon Shin、Hee Jae Shin、Hye-Kyeong Kim、Hyi-Seung Lee

  DOI：10.1016/j.bmcl.2007.11.003

  日期：2008.1

  A series of bromophenols was obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine. New bromophenols including 3,3,5,5'-tetrabromo-2,2',4,4'-tetrahydroxydiphenylmethane (10), a regioisomer of the potent antimicrobial natural product, together with known derivatives were synthesized in high yield. All of the isolated and synthesized compounds were tested for antimicrobial activity against Gram-negative, Gram-positive bacteria and fungi. The preliminary structure-activity relationship, to elucidate the essential structure requirements for antimicrobial activity, has been described. Among the isolated natural products 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane (4) was found to be the most active derivative against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. The synthetic bromophenols 3,3'-dibromo-6,6'-dihydroxydiphenylmethane (13) and 3,3',5,5'-tetrabromo-6, 6'-dihydroxydiphenylmethane (14) showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus. Proteus vulgaris, and Salmonella typhimurium. (C) 2007 Elsevier Ltd. All rights reserved.