3-(4-dimethylaminophenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)propenone

• 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-(4-dimethylaminophenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)propenone
• 英文别名: (E)-3-[4-(dimethylamino)phenyl]-1-(5-hydroxy-2,2-dimethylchroman-6-yl)prop-2-en-1-one；(E)-3-(4-dimethylaminophenyl)-1-(5-hydroxy-2,2-dimethyl-chroman-6-yl)prop-2-en-1-one；(E)-3-[4-(dimethylamino)phenyl]-1-(5-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)prop-2-en-1-one
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: CDRANEIDFOYMQJ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-dimethylaminophenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)propenone 在 sodium acetate 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.06h， 以82%的产率得到6-{5-[4-(dimethylamino)phenyl]-4,5-dihydro-1Hpyrazol-3-yl}-2,2-dimethylchroman-7-ol
  参考文献：
  名称：

  Microwave-assisted synthesis and antimicrobial evaluation of novel pyrazolines

  摘要：

  A series of 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethylchroman-7-ol and 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethyl-chroman-5-ol derivatives have been synthesized from the corresponding chalcones and hydrazine hydrate in the presence of sodium acetate under microwave irradiation involving the Michael addition followed by cycloaddition. All the newly synthesized 18 compounds were screened for their in vitro antimicrobial activity. Most of the compounds displayed very good to excellent antimicrobial activity in comparison to standard drugs streptomycin and nystatin.

  DOI：

  10.1007/s10593-015-1790-6
• 作为产物：
  描述：

  (E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-[4-(dimethylamino)phenyl]prop-2-en-1-one 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以91%的产率得到3-(4-dimethylaminophenyl)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)propenone
  参考文献：
  名称：

  BF3–Et2O mediated biogenetic type synthesis of chromanochalcones from prenylated chalcones via a regioselective cyclization reaction

  摘要：

  In continuation of out-program on synthetic chalcones. we have developed a simple and convenient method for the synthesis of chromanochalcones from prenylated chalcones in high yields by regioselective cyclization using BF3-Et2O. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.124

文献信息

• Microwave-assisted synthesis and antimicrobial evaluation of novel pyrazolines
  作者：Ashok Dongamanti、Mohan Gandhi Devulapally、Vikas Kumar Aamate、Srinivas Gundu

  DOI：10.1007/s10593-015-1790-6

  日期：2015.10

  A series of 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethylchroman-7-ol and 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethyl-chroman-5-ol derivatives have been synthesized from the corresponding chalcones and hydrazine hydrate in the presence of sodium acetate under microwave irradiation involving the Michael addition followed by cycloaddition. All the newly synthesized 18 compounds were screened for their in vitro antimicrobial activity. Most of the compounds displayed very good to excellent antimicrobial activity in comparison to standard drugs streptomycin and nystatin.
• BF3–Et2O mediated biogenetic type synthesis of chromanochalcones from prenylated chalcones via a regioselective cyclization reaction
  作者：T. Narender、K. Papi Reddy

  DOI：10.1016/j.tetlet.2007.08.124

  日期：2007.10

  In continuation of out-program on synthetic chalcones. we have developed a simple and convenient method for the synthesis of chromanochalcones from prenylated chalcones in high yields by regioselective cyclization using BF3-Et2O. (C) 2007 Elsevier Ltd. All rights reserved.