α-phenyl-N-(4-cyanophenyl)nitrone | 534556-64-4

• 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: α-phenyl-N-(4-cyanophenyl)nitrone
• 英文别名: N-(4-cyanophenyl)-1-phenylmethanimine oxide
• CAS: 534556-64-4；115399-99-0
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: YDCHRUZECCBONG-WJDWOHSUSA-N

物化性质

• 沸点：
  422.4±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-morpholin-4-yl-acrylonitrile 、 α-phenyl-N-(4-cyanophenyl)nitrone 以 甲苯 为溶剂， 反应 4.0h， 以47%的产率得到4-(3-morpholin-4-yl-3-oxo-1-phenyl-propylamino)benzonitrile
  参考文献：
  名称：

  在衍生自C，N-二芳基硝酮和2-吗啉-4-基-丙烯腈的异恶唑烷的热重排中，芳基苄基氮离子具有中介作用的证据。

  摘要：

  与二芳基，二烷基，烷基芳基和母体系列相反，对芳基苄基氮离子的产生和化学行为一无所知。在这里，我们报告这些物种可以通过涉及C，N-二芳基亚硝基和2-吗啉-4-基-丙烯腈的异恶唑烷的空前热重排的过程生成。这些反应的产物极大地取决于硝酮的性质。大多数观察到的化学反应均来自单重态。

  DOI：

  10.1002/chem.200390102
• 作为产物：
  描述：

  达比加群酯杂质32 、 苯甲醛 以 乙醇 为溶剂， 生成 α-phenyl-N-(4-cyanophenyl)nitrone
  参考文献：
  名称：

  ¹³C and¹H NMR of Arylnitrones. Substituent Effects of α-Phenyl-N-(p-substituted phenyl)nitrones

  摘要：

  研究了取代基对 α-苯基-N-芳基硝基腈 (2) 共轭位点化学位移的影响。共振效应在这些位置上占主导地位。取代基的电子效应应在供电子基团和吸电子基团之间分开处理。研究还提出了 2 中取代基效应传递的合理机制。

  DOI：

  10.1246/bcsj.60.3607

文献信息

• WEST, PAUL R.;DAVIS, GARY C., J. ORG. CHEM., 54,(1989) N1, C. 5176-5180
  作者：WEST, PAUL R.、DAVIS, GARY C.

  DOI：——

  日期：——
• SPIRO DERIVATIVES OF PARTHENIN AS NOVEL ANTICANCER AGENTS
  申请人：Council Of Scientific & Industrial Research

  公开号：EP2265620A1

  公开（公告）日：2010-12-29
• Spiro Derivatives of Parthenin as Novel Anticancer Agents
  申请人：Halmuthur Mahabalarao Sampath Kumar

  公开号：US20110201661A1

  公开（公告）日：2011-08-18

  The present invention relates to novel spiro derivatives of parthenin prepared by the dipolar cycloaddition of various dipoles viz, benzonitrile oxides, nitrones, azides, nitrile ylide diazoalkane, nitrile imide, ozone, azomethine imides, azomethine ylides etc. with exocyclic double bond of C ring (α-methylene-γ-butyrolactone). Representative compounds have been screened for their anticancer activity against different cancer cell lines. ICs0 value of these analogues varies between 4.3 μM to 93 μM. A mechanistic correlation of their anticancer activity has been described. The results of the cytotoxicity test of the compounds studies indicated that the α,β-unsaturated ketonic moiety in parthenin plays an important role in the maintenance of the high level of cytotoxicity.
• US8609858B2
  申请人：——

  公开号：US8609858B2

  公开（公告）日：2013-12-17
• [EN] SPIRO DERIVATIVES OF PARTHENIN AS NOVEL ANTICANCER AGENTS<br/>[FR] DÉRIVÉS SPIRO DE PARTHÉNINE SERVANT DE NOUVEAUX AGENTS ANTICANCÉREUX
  申请人：COUNCIL QF SCIENT & IND RES

  公开号：WO2009110007A1

  公开（公告）日：2009-09-11

  The present invention relates to novel spiro derivatives of parthenin prepared by the dipola cycloaddition of various dipoles viz, benzonitrile oxides, nitrones, azides, nitrile ylide diazoalkane, nirile imide, ozone, azomethine imides, azomethine ylides etc. with exocycli double bond of C ring (α-methylene-γ-butyrolactone). Representative compounds have bee screened for their anticancer activity against different cancer cell lines. ICs0 value of thes analogues varies between 4.3 μM to 93 μM. A mechanistic correlation of their anticance activity has been described. The results of the cytotoxicity test of the compounds studie indicated that the α, β-unsaturated ketonic moity in parthenin plays an important role in th maintenance of the high level of cytotoxicity.