3-isopropyl-4-ethylacetophenone | 110224-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropyl-4-ethylacetophenone
• 英文别名: 1-(4-Ethyl-3-propan-2-ylphenyl)ethanone
• CAS: 110224-70-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: JNBWOMUFTHJBIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-isopropyl-4-ethylacetophenone 、 胍 以31%的产率得到
  参考文献：
  名称：

  ROTH, BARBARA;AIG, EDWARD, J. MED. CHEM., 30,(1987) N 11, 1998-2004

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙基苯乙酮 、 2-溴丙烷 在 三氯化铝 作用下， 反应 18.0h， 以11.5 g的产率得到3-isopropyl-4-ethylacetophenone
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 8. The 3,4,5-triethyl isostere of trimethoprim. A study of specificity

  摘要：

  3,4,5-Triethylacetophenone was synthesized in 60% yield by a Friedel-Crafts reaction from 4-ethylacetophenone and converted to 2,4-diamino-5-(3,4,5-triethylbenzyl)pyrimidine (2), a trimethoprim (1) isostere, by standard techniques. This compound is more lipophilic than 1 by three log units (log P, octanol/water). Compound 2 was approximately equipotent with 1 in inhibiting Escherichia coli dihydrofolate reductase (DHFR), 2-fold more potent against P. berghei and N. gonorrhoeae DHFR, and 10 and 25 times better an inhibitor of rat and chicken liver DHFR, respectively. Although the 3,4-dimethoxy analogue 19 was 10-fold less inhibitory to E. coli DHFR than 1, it was 3-4 times more potent on the vertebrate isozymes, whereas the diethyl congener 10 followed 19 in its E. coli DHFR binding but was less active on rat and chicken DHFR. Therefore, a significant portion of the selectivity of 1 for bacterial, as opposed to vertebrate, DHFR, involves the methoxy functions. An analysis of the X-ray data on 1 and 2 complexed with chicken DHFR, coupled with kinetic data, led to the conclusion that the difference in binding energies of the methoxy and ethyl compounds probably involve desolvation factors, as well as direct energies of interaction with protein atoms. Thus, one cannot invoke lipophilicity or shape alone in explaining the relationship in properties of 1 and 2.

  DOI：

  10.1021/jm00394a012

文献信息

• ROTH, BARBARA;AIG, EDWARD, J. MED. CHEM., 30,(1987) N 11, 1998-2004
  作者：ROTH, BARBARA、AIG, EDWARD

  DOI：——

  日期：——
• Novel red electroluminescent compounds and organic electroluminescent device using the same
  申请人：Gracel Display Inc.

  公开号：EP2053112B1

  公开（公告）日：2011-08-24
• 2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 8. The 3,4,5-triethyl isostere of trimethoprim. A study of specificity
  作者：Barbara Roth、Edward Aig

  DOI：10.1021/jm00394a012

  日期：1987.11

  3,4,5-Triethylacetophenone was synthesized in 60% yield by a Friedel-Crafts reaction from 4-ethylacetophenone and converted to 2,4-diamino-5-(3,4,5-triethylbenzyl)pyrimidine (2), a trimethoprim (1) isostere, by standard techniques. This compound is more lipophilic than 1 by three log units (log P, octanol/water). Compound 2 was approximately equipotent with 1 in inhibiting Escherichia coli dihydrofolate reductase (DHFR), 2-fold more potent against P. berghei and N. gonorrhoeae DHFR, and 10 and 25 times better an inhibitor of rat and chicken liver DHFR, respectively. Although the 3,4-dimethoxy analogue 19 was 10-fold less inhibitory to E. coli DHFR than 1, it was 3-4 times more potent on the vertebrate isozymes, whereas the diethyl congener 10 followed 19 in its E. coli DHFR binding but was less active on rat and chicken DHFR. Therefore, a significant portion of the selectivity of 1 for bacterial, as opposed to vertebrate, DHFR, involves the methoxy functions. An analysis of the X-ray data on 1 and 2 complexed with chicken DHFR, coupled with kinetic data, led to the conclusion that the difference in binding energies of the methoxy and ethyl compounds probably involve desolvation factors, as well as direct energies of interaction with protein atoms. Thus, one cannot invoke lipophilicity or shape alone in explaining the relationship in properties of 1 and 2.