1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine | 74880-17-4

• 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: 1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine
• 英文别名: 1-benzyl-2-methylpyrrolid-3-one oxime；1-Benzyl-3-hydroxyimino-2-methylpyrrolidine；N-(1-benzyl-2-methylpyrrolidin-3-ylidene)hydroxylamine
• CAS: 74880-17-4
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: QYXRREXPAUULFK-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine 在 镍 ammonium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 nemonapride
  参考文献：
  名称：

  Synthesis and neuroleptic activity of benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide and related compounds

  摘要：

  Three series of benzamides of N,N-disubstituted ethylenediamines (linear alkane-1,2-diamines), 1-substituted 2-(aminomethyl)pyrrolidines, and 1-substituted 3-aminopyrrolidines (cyclic alkane-1,2-diamines) were designed and synthesized as potential neuroleptics. All target compounds were evaluated for their inhibitory effects on apomorphine-induced stereotyped behavior in rats, and a good correlation between structure and activity was found throughout the series. In the linear series (analogues of metoclopramide), introduction of a benzyl group on the terminal nitrogen, rather than an ethyl group, and a methyl group on the p-amino group of metoclopramide both enhanced the activity. The resulting N-[2-(N-benzyl-N-methylamino)ethyl]-5-chloro-2-methoxy-4-(methylamino) benzamide(23) was about 15 times more active than metoclopramide. In the cyclic series, particularly among the benzamides of 1-benzyl-3-aminopyrrolidine, most of the compounds tested were more active than the corresponding linear benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino) benzamide (YM-09151-2, 55) was the most active among all of the compounds tested, being 13 and 408 times more potent than haloperidol and metoclopramide, respectively. Moreover, compound 55 exhibited a fairly high ratio of antistereotypic activity to cataleptogenicity compared with haloperidol and metoclopramide. It is expected that compound 55 may be used as a potent drug with few side effects in the treatment of psychosis.

  DOI：

  10.1021/jm00142a019
• 作为产物：
  描述：

  (α-ethoxycarbonylethyl)-β-ethoxycarbonylethylbenzylamine 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 1-benzyl-3-(hydroxyimino)-2-methylpyrrolidine
  参考文献：
  名称：

  Heterocyclization of Oximes of 3,5-Dimethyl(1,3,5-trimethyl)-2,6-diphenylpiperid-4-ones and N-Benzylpyrrolid-3-ones with Acetylene in a Superbasic Medium

  摘要：

  DOI：

  10.1023/b:cohc.0000028629.93231.b8

文献信息

• Benzamide derivatives
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US04210660A1

  公开（公告）日：1980-07-01

  Benzamide derivatives represented by the formula ##STR1## wherein X represents a lower alkoxy group; Y represents a mono- or di-lower alkylamino group; Z represents a halogen atom; R.sub.1 represents a lower alkyl group; and R.sub.2 represents a hydrogen atom or a halogen atom, and their pharmacologically acceptable nontoxic salts, which are strong central nervous system depressants, in particular strong antipsychotics.

  公式如下：##STR1## 其中X代表低级烷氧基；Y代表单个或双个低级烷基氨基；Z代表卤素原子；R.sub.1代表低级烷基；R.sub.2代表氢原子或卤素原子，以及它们的药理学上可接受的无毒盐，这些盐是强的中枢神经系统抑制剂，特别是强的抗精神病药物。
• Synthesis and neuroleptic activity of benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide and related compounds
  作者：Sumio Iwanami、Mutsuo Takashima、Yasufumi Hirata、Osamu Hasegawa、Shinji Usuda

  DOI：10.1021/jm00142a019

  日期：1981.10

  Three series of benzamides of N,N-disubstituted ethylenediamines (linear alkane-1,2-diamines), 1-substituted 2-(aminomethyl)pyrrolidines, and 1-substituted 3-aminopyrrolidines (cyclic alkane-1,2-diamines) were designed and synthesized as potential neuroleptics. All target compounds were evaluated for their inhibitory effects on apomorphine-induced stereotyped behavior in rats, and a good correlation between structure and activity was found throughout the series. In the linear series (analogues of metoclopramide), introduction of a benzyl group on the terminal nitrogen, rather than an ethyl group, and a methyl group on the p-amino group of metoclopramide both enhanced the activity. The resulting N-[2-(N-benzyl-N-methylamino)ethyl]-5-chloro-2-methoxy-4-(methylamino) benzamide(23) was about 15 times more active than metoclopramide. In the cyclic series, particularly among the benzamides of 1-benzyl-3-aminopyrrolidine, most of the compounds tested were more active than the corresponding linear benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino) benzamide (YM-09151-2, 55) was the most active among all of the compounds tested, being 13 and 408 times more potent than haloperidol and metoclopramide, respectively. Moreover, compound 55 exhibited a fairly high ratio of antistereotypic activity to cataleptogenicity compared with haloperidol and metoclopramide. It is expected that compound 55 may be used as a potent drug with few side effects in the treatment of psychosis.
• Heterocyclization of Oximes of 3,5-Dimethyl(1,3,5-trimethyl)-2,6-diphenylpiperid-4-ones and N-Benzylpyrrolid-3-ones with Acetylene in a Superbasic Medium
  作者：L. G. Voskressensky、T. N. Borisova、A. V. Varlamov

  DOI：10.1023/b:cohc.0000028629.93231.b8

  日期：2004.3