benzylidene-(3-chloro-1-propylamine) | 1026774-25-3

• 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: benzylidene-(3-chloro-1-propylamine)
• CAS: 1026774-25-3
• 化学式: C₁₀H₁₂ClN
• 分子量: 181.665
• InChiKey: YHDGLXVVWLCNHG-FMIVXFBMSA-N

物化性质

• 沸点：
  270.1±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  benzylidene-(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-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 、 苯甲醛 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到benzylidene-(3-chloro-1-propylamine)
  参考文献：
  名称：

  N-（ω-卤代烷基）-β-内酰胺对氢化铝锂的反应性：1-（1-芳基-3-羟丙基）氮丙啶和3-芳基-3-（N-丙基氨基）丙烷-1的新颖合成-ols。

  摘要：

  首次评估了4-芳基-1-（2-氯乙基）氮杂环丁烷-2-酮和4-芳基-1-（3-溴丙基）氮杂环丁烷-2-酮对氢化铝锂的反应性。通过将β-内酰胺前所未有地转化为2,3-未取代的氮丙啶衍生物，将4-芳基-1-（2-氯乙基）氮杂环丁烷-2-酮转化为新型的1-（1-芳基-3-羟丙基）氮丙啶。出乎意料的是，在使用LiAlH（4）处理后，4-芳基-1-（3-溴丙基）氮杂环丁烷-2-酮经历了向3-芳基-3-（N-丙基氨基）丙烷-1-醇的脱卤反应。通过使用苄基溴在乙腈中向3-芳基-3- [N-苄基-N-（2-溴乙基）氨基]丙烷-1的开环反应进一步修饰1-（1-芳基-3-羟丙基）氮丙啶-醇，并使用氯化铝（iii）在乙醚中，得到3-芳基-3- [N-（2-氯乙基）氨基]丙烷-1-醇。

  DOI：

  10.1039/b719686e

文献信息

• Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors
  作者：Andrew Morrell、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1016/j.bmcl.2004.05.022

  日期：2004.7

  Indenoisoquinolines and dihydroindenoisoquinolines have been synthesized possessing a nitro-substituted isoquinoline ring in an effort to explore the effects of electron-withdrawing substituents on biological activity. The in vitro anticancer activities of these molecules have been tested in the National Cancer Institute's screen of 55 cell lines. The compounds have also been tested for topoisomerase I (topI) inhibition. The results indicate that these substances are a potent class of topI inhibitors with sub-micromolar cytotoxicity mean graph midpoints (MGM) and topI inhibition equal to camptothecin. (C) 2004 Elsevier Ltd. All rights reserved.
• Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors
  作者：Andrew Morrell、Michael Placzek、Seth Parmley、Brian Grella、Smitha Antony、Yves Pommier、Mark Cushman

  DOI：10.1021/jm070307+

  日期：2007.9.1

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.
• MADZAKI, MITSUO;SINTO, NAOYA;XASIMOTO, KOITI;SINODZAKI, ATSUXIKO
  作者：MADZAKI, MITSUO、SINTO, NAOYA、XASIMOTO, KOITI、SINODZAKI, ATSUXIKO

  DOI：——

  日期：——
• US4212877A
  申请人：——

  公开号：US4212877A

  公开（公告）日：1980-07-15
• US4256756A
  申请人：——

  公开号：US4256756A

  公开（公告）日：1981-03-17