Cyclopropyl-[4-[(4-methoxyphenyl)methoxy]phenyl]methanone | 868699-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cyclopropyl-[4-[(4-methoxyphenyl)methoxy]phenyl]methanone
• CAS: 868699-42-7
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: NFUCXOAZGFSXJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cyclopropyl-[4-[(4-methoxyphenyl)methoxy]phenyl]methanone 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 1-[{4-(4-methoxybenzyloxy)phenyl}(cyclopropyl)methyl]-1H-1,2,4-triazole
  参考文献：
  名称：

  鉴定1- [4-苄氧基苯基）-丁-3-烯基] -1H-唑类为新型抗结核药和抗微生物剂。

  摘要：

  一系列的1-[（4-苄氧基苯基）-丁-3-烯基] -1H-唑已被鉴定为针对结核分枝杆菌的有效抗结核药。化合物的合成涉及苯环丙基甲醇的环丙基环的酸催化开环，然后吡咯对碳正离子中间体的亲核攻击。与许多标准药物相比，几种化合物26、34和36表现出显着的抗结核活性，MIC值分别低至1.56、1.56和0.61马克/毫升。这些化合物还针对其他细菌和真菌菌株进行了筛选，并且其中很少有人显示出对引起肺部感染的烟曲霉具有良好的抗真菌活性。

  DOI：

  10.1021/ml4002248
• 作为产物：
  描述：

  4-氯-4'-氟苯丁酮 、 4-甲氧基苄醇 在 四丁基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 Cyclopropyl-[4-[(4-methoxyphenyl)methoxy]phenyl]methanone
  参考文献：
  名称：

  An efficient synthesis of aryloxyphenyl cyclopropyl methanones: a new class of anti-mycobacterial agents

  摘要：

  An efficient, high yield and one-pot synthesis of phenyl cyclopropyl methanones by reaction of different aryl alcohols with 4'-fluoro-4-chloro-butyrophenone in THF/DMF in the presence of NaH/TBAB is reported. Most of the methanones were further reduced to respective alcohols or methylenes. All the compounds were evaluated for their anti-tubercular activities against M. tuberculosis H37Rv in vitro displaying MICs ranging from 25 to 3.125 mu g/mL. The most active compounds showed activity against MDR strains and two of them (14 and 16) showed marginal enhancement of MST in mice. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.007

文献信息

• An efficient synthesis of aryloxyphenyl cyclopropyl methanones: a new class of anti-mycobacterial agents
  作者：Namrata Dwivedi、Neetu Tewari、V.K. Tiwari、Vinita Chaturvedi、Y.K. Manju、A. Srivastava、A. Giakwad、S. Sinha、R.P. Tripathi

  DOI：10.1016/j.bmcl.2005.07.007

  日期：2005.10

  An efficient, high yield and one-pot synthesis of phenyl cyclopropyl methanones by reaction of different aryl alcohols with 4'-fluoro-4-chloro-butyrophenone in THF/DMF in the presence of NaH/TBAB is reported. Most of the methanones were further reduced to respective alcohols or methylenes. All the compounds were evaluated for their anti-tubercular activities against M. tuberculosis H37Rv in vitro displaying MICs ranging from 25 to 3.125 mu g/mL. The most active compounds showed activity against MDR strains and two of them (14 and 16) showed marginal enhancement of MST in mice. (c) 2005 Elsevier Ltd. All rights reserved.
• Identification of 1-[4-Benzyloxyphenyl)-but-3-enyl]-1<i>H</i>-azoles as New Class of Antitubercular and Antimicrobial Agents
  作者：Namrata Anand、K. K. G. Ramakrishna、Munna P. Gupt、Vinita Chaturvedi、Shubhra Singh、Kishore K. Srivastava、Prapunjika Sharma、Niyati Rai、Ravishankar Ramachandran、A. K. Dwivedi、Varsha Gupta、Brijesh Kumar、Smriti Pandey、Praveen K. Shukla、Shailandra K. Pandey、Jawahar Lal、Rama Pati Tripathi

  DOI：10.1021/ml4002248

  日期：2013.10.10

  A series of 1-[(4-benzyloxyphenyl)-but-3-enyl]-1H-azoles has been identified as potent antitubercular agents against Mycobacterium tuberculosis. Synthesis of compounds involved acid catalyzed ring-opening of cyclopropyl ring of phenyl cyclopropyl methanols followed by nucleophilic attack of the azoles on the carbocation intermediates. Several of the compounds 26, 34, and 36 exhibited significant antitubercular

  一系列的1-[（4-苄氧基苯基）-丁-3-烯基] -1H-唑已被鉴定为针对结核分枝杆菌的有效抗结核药。化合物的合成涉及苯环丙基甲醇的环丙基环的酸催化开环，然后吡咯对碳正离子中间体的亲核攻击。与许多标准药物相比，几种化合物26、34和36表现出显着的抗结核活性，MIC值分别低至1.56、1.56和0.61马克/毫升。这些化合物还针对其他细菌和真菌菌株进行了筛选，并且其中很少有人显示出对引起肺部感染的烟曲霉具有良好的抗真菌活性。