3-methoxybenzylidene-(3-chloro-1-propylamine)

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxybenzylidene-(3-chloro-1-propylamine)
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: XVRKKSCDXUORDA-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methoxybenzylidene-(3-chloro-1-propylamine) 在 di(tert-butyl)-biphenyl 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(3-甲氧苯基)-吡咯烷
  参考文献：
  名称：

  Hammett Correlation of Nornicotine Analogues in the Aqueous Aldol Reaction:  Implications for Green Organocatalysis

  摘要：

  A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with rho = 1.14 (R-2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organo-catalyst.

  DOI：

  10.1021/jo050161r
• 作为产物：
  描述：

  3-氯丙胺盐酸盐 、 3-甲氧基苯甲醛 在 三乙胺 、 magnesium sulfate 作用下， 以 氯仿 为溶剂， 反应 16.08h， 以97%的产率得到3-methoxybenzylidene-(3-chloro-1-propylamine)
  参考文献：
  名称：

  A Systematic Study of Nitrated Indenoisoquinolines Reveals a Potent Topoisomerase I Inhibitor

  摘要：

  The biological activity of indenoisoquinoline topoisomerase I inhibitors is significantly enhanced by nitration of the isoquinoline ring. In the present study, nitrated analogues were synthesized with the indenone ring substituted with methoxy groups to further explore a previously identified structure-activity relationship between the nitrated isoquinoline ring and a methylenedioxy-substituted indenone ring. The results indicate that a single methoxy group at the 9-position of an indenoisoquinoline affords superior biological activity. Hypothetical binding models have been developed to rationalize these results, and they indicate that pi-stacking between the indenoisoquinolines and the DNA base pairs, as visualized by electrostatic complementarity, is important for the intercalation and biological activity of the indenoisoquinoline analogues. Collectively, the analysis of methoxy groups on the indenone ring also illustrates a strict steric requirement for substituents extending toward the nonscissile DNA backbone and emphasizes a need for planarity to afford potent biological activity.

  DOI：

  10.1021/jm060974n

文献信息

• Hammett Correlation of Nornicotine Analogues in the Aqueous Aldol Reaction:  Implications for Green Organocatalysis
  作者：Claude J. Rogers、Tobin J. Dickerson、Andrew P. Brogan、Kim D. Janda

  DOI：10.1021/jo050161r

  日期：2005.4.1

  A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with rho = 1.14 (R-2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organo-catalyst.
• A Systematic Study of Nitrated Indenoisoquinolines Reveals a Potent Topoisomerase I Inhibitor
  作者：Andrew Morrell、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1021/jm060974n

  日期：2006.12.1

  The biological activity of indenoisoquinoline topoisomerase I inhibitors is significantly enhanced by nitration of the isoquinoline ring. In the present study, nitrated analogues were synthesized with the indenone ring substituted with methoxy groups to further explore a previously identified structure-activity relationship between the nitrated isoquinoline ring and a methylenedioxy-substituted indenone ring. The results indicate that a single methoxy group at the 9-position of an indenoisoquinoline affords superior biological activity. Hypothetical binding models have been developed to rationalize these results, and they indicate that pi-stacking between the indenoisoquinolines and the DNA base pairs, as visualized by electrostatic complementarity, is important for the intercalation and biological activity of the indenoisoquinoline analogues. Collectively, the analysis of methoxy groups on the indenone ring also illustrates a strict steric requirement for substituents extending toward the nonscissile DNA backbone and emphasizes a need for planarity to afford potent biological activity.