(R)-1-n-butyl-2-aminomethyltetrahydropyrrole | 130981-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-1-n-butyl-2-aminomethyltetrahydropyrrole
• 英文别名: (R)-2-(aminomethyl)-1-n-butylpyrrolidine；(R)-(+)-2-aminomethyl-1-butylpyrrolidine；[(2R)-1-butylpyrrolidin-2-yl]methanamine
• CAS: 130981-39-4
• 化学式: C₉H₂₀N₂
• 分子量: 156.271
• InChiKey: VRKXUSCKISXSIH-SECBINFHSA-N

物化性质

• 沸点：
  66-67 °C(Press: 0.6 Torr)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-n-butyl-2-aminomethyltetrahydropyrrole 、 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (2R,2R)-N-<(1-n-butyl-2-pyrrolidinyl)methyl>-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide
  参考文献：
  名称：

  Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides

  摘要：

  The stereoisomers of some N-[(1-alkyl-2-pyrrolidinyl)methyl]5-sulfamoylbenzamides (3-8) and -2,3-dihydrobenzofuran-7-carboxamides (9-18) were prepared to compare their dopamine D2 receptor binding affinities (in vitro) and inhibitory effects on apomorphine-induced hyperactivity (in vivo). In the 1-ethyl substituted compounds of the two series, the stereoisomers with S absolute configuration at the 2-position of the pyrrolidine moiety (S enantiomer 3 and 2S diastereomers 9 and 10) were more potent in both of the above activities than those with R absolute configuration (R enantiomer 4 and 2R diastereomers 11 and 12, respectively), whereas the R enantiomer (8) was more potent than the S enantiomer (7) in the 1-n-hexyl-substituted-benzamides and the 2R diastereomers (15, 16, and 18) were more potent than the 2S diastereomers (13, 14, and 17) in the 1-n-butyl- and 1-n-hexyl-2,3-dihydrobenzofuran-7-carboxamies. It was found that the stereospecificity of the compound activities altered from the S configuration to the R configuration as the 1-alkyl side chain became longer in the two series. How these stereoisomers meet the configurational requirements to interact with the dopamine D2 receptors is also discussed.

  DOI：

  10.1021/jm00105a041
• 作为产物：
  描述：

  2-aminomethyl-1-butyl pyrrolidine 生成 (R)-1-n-butyl-2-aminomethyltetrahydropyrrole
  参考文献：
  名称：

  Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides

  摘要：

  The stereoisomers of some N-[(1-alkyl-2-pyrrolidinyl)methyl]5-sulfamoylbenzamides (3-8) and -2,3-dihydrobenzofuran-7-carboxamides (9-18) were prepared to compare their dopamine D2 receptor binding affinities (in vitro) and inhibitory effects on apomorphine-induced hyperactivity (in vivo). In the 1-ethyl substituted compounds of the two series, the stereoisomers with S absolute configuration at the 2-position of the pyrrolidine moiety (S enantiomer 3 and 2S diastereomers 9 and 10) were more potent in both of the above activities than those with R absolute configuration (R enantiomer 4 and 2R diastereomers 11 and 12, respectively), whereas the R enantiomer (8) was more potent than the S enantiomer (7) in the 1-n-hexyl-substituted-benzamides and the 2R diastereomers (15, 16, and 18) were more potent than the 2S diastereomers (13, 14, and 17) in the 1-n-butyl- and 1-n-hexyl-2,3-dihydrobenzofuran-7-carboxamies. It was found that the stereospecificity of the compound activities altered from the S configuration to the R configuration as the 1-alkyl side chain became longer in the two series. How these stereoisomers meet the configurational requirements to interact with the dopamine D2 receptors is also discussed.

  DOI：

  10.1021/jm00105a041

文献信息

• Benzazine compounds and pharmaceutical uses thereof
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US05185333A1

  公开（公告）日：1993-02-09

  A benzazine compound, a geometrical isomer of said benzazine compound, an optical isomer of said benzazine compound, and a pharmaceutically acceptable salt of said benzazine compound, said benzazine compound being represented by formula (I): ##STR1## wherein each symbol is as defined in the specification. Said benzazine compounds exhibit 5-HT.sub.3 receptor antagonistic activity, and 5-HT.sub.1A receptor and/or 5-HT.sub.2 receptor and/or dopamine D.sub.2 receptor blocking activity so that they are useful as drugs for the prophylaxis or treatment of various digestive diseases vomiting and disturbances in central nervous systems and the like. The intermediates for said benzazine compounds are also disclosed.

  一种苯嗪化合物，所述苯嗪化合物的几何异构体，所述苯嗪化合物的光学异构体，以及所述苯嗪化合物的药学可接受的盐，其中所述苯嗪化合物由式（I）表示：##STR1##其中每个符号如规范中定义。所述苯嗪化合物表现出5-HT.sub.3受体拮抗活性，以及5-HT.sub.1A受体和/或5-HT.sub.2受体和/或多巴胺D.sub.2受体阻断活性，因此它们可用作用于预防或治疗各种消化疾病、呕吐和中枢神经系统紊乱等药物。所述苯嗪化合物的中间体也被披露。
• 手性胺基酚氧基锌、镁化合物及其制备方法和 应用
  申请人：华东理工大学

  公开号：CN103787943B

  公开（公告）日：2016-06-15

  本发明公开了一类多手性中心胺基酚氧基锌、镁化合物及其制备方法和在高活性、高选择性催化内酯开环聚合中的应用。其制备方法包括如下步骤：将中性配体直接与金属原料化合物在有机介质中反应，然后经过滤、浓缩、重结晶步骤获得目标化合物。本发明的手性胺基酚氧基锌、镁化合物是一种高效的内酯开环聚合催化剂，可用于催化丙交酯等的聚合反应；特别对于外消旋丙交酯可得到较高等规度或杂规度的聚乳酸。本发明的手性胺基酚氧基锌、镁化合物优点十分明显：原料易得，合成路线简单，产物收率高，具有较高的催化活性和立体选择性，能获得高规整度、高分子量聚酯材料，能够满足工业部门的需要。其结构式如下所示：
• MURAKAMI, SHU;MARUBAYASHI, NOBUHIRO;FUKUDA, TAKEMI;TAKEHARA, SHUZO;TAHARA+, J. MED. CHEM., 34,(1991) N, C. 261-267
  作者：MURAKAMI, SHU、MARUBAYASHI, NOBUHIRO、FUKUDA, TAKEMI、TAKEHARA, SHUZO、TAHARA+

  DOI：——

  日期：——
• US5185333A
  申请人：——

  公开号：US5185333A

  公开（公告）日：1993-02-09
• Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides
  作者：Shu Murakami、Nobuhiro Marubayashi、Takemi Fukuda、Shuzo Takehara、Tetsuya Tahara

  DOI：10.1021/jm00105a041

  日期：1991.1

  The stereoisomers of some N-[(1-alkyl-2-pyrrolidinyl)methyl]5-sulfamoylbenzamides (3-8) and -2,3-dihydrobenzofuran-7-carboxamides (9-18) were prepared to compare their dopamine D2 receptor binding affinities (in vitro) and inhibitory effects on apomorphine-induced hyperactivity (in vivo). In the 1-ethyl substituted compounds of the two series, the stereoisomers with S absolute configuration at the 2-position of the pyrrolidine moiety (S enantiomer 3 and 2S diastereomers 9 and 10) were more potent in both of the above activities than those with R absolute configuration (R enantiomer 4 and 2R diastereomers 11 and 12, respectively), whereas the R enantiomer (8) was more potent than the S enantiomer (7) in the 1-n-hexyl-substituted-benzamides and the 2R diastereomers (15, 16, and 18) were more potent than the 2S diastereomers (13, 14, and 17) in the 1-n-butyl- and 1-n-hexyl-2,3-dihydrobenzofuran-7-carboxamies. It was found that the stereospecificity of the compound activities altered from the S configuration to the R configuration as the 1-alkyl side chain became longer in the two series. How these stereoisomers meet the configurational requirements to interact with the dopamine D2 receptors is also discussed.