(1E,4E)-1-(2-nitrophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one | 1403252-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1E,4E)-1-(2-nitrophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-(2-nitrophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
• CAS: 1403252-62-9
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: HDFNORZPAYGLDS-AQASXUMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(2-nitrophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one 在 一水合肼 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以41%的产率得到(E)-2-(2-(2,6,6-trimethylcyclohex-1-en-1-yl)vinyl)quinoline 1-oxide
  参考文献：
  名称：

  N₂H₄–H₂O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides

  摘要：

  DOI：

  10.1021/acs.orglett.0c04162
• 作为产物：
  描述：

  beta-紫罗酮 、 邻硝基苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以93%的产率得到(1E,4E)-1-(2-nitrophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  N₂H₄–H₂O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides

  摘要：

  DOI：

  10.1021/acs.orglett.0c04162

文献信息

• Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles
  作者：Avinash Tiwari、Santosh Kumar、S.N. Suryawanshi、Monika Mittal、Preeti Vishwakarma、Suman Gupta

  DOI：10.1016/j.bmcl.2012.10.110

  日期：2013.1

  Some novel alpha and beta ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49 mu M and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent. (c) 2012 Elsevier Ltd. All rights reserved.
• N₂H₄–H₂O Enabled Umpolung Cyclization of <i>o</i>-Nitro Chalcones for the Construction of Quinoline <i>N</i>-Oxides
  作者：Guan Zhang、Kai Yang、Shihui Wang、Qiang Feng、Qiuling Song

  DOI：10.1021/acs.orglett.0c04162

  日期：2021.1.15