(S)-(1-ⁿbutylpyrrolidin-2-yl)methanamine | 130981-38-3

• 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: (S)-(1-ⁿbutylpyrrolidin-2-yl)methanamine
• 英文别名: (S)-1-n-butyl-2-aminomethyltetrahydropyrrole；(S)-(1-n-butylpyrrolidin-2-yl)methanamine；(S)-2-(aminomethyl)-1-n-butylpyrrolidine；(s)-(-)-2-aminomethyl-1-butylpyrrolidine；[(2S)-1-butylpyrrolidin-2-yl]methanamine
• CAS: 130981-38-3
• 化学式: C₉H₂₀N₂
• 分子量: 156.271
• InChiKey: VRKXUSCKISXSIH-VIFPVBQESA-N

物化性质

• 沸点：
  105 °C(Press: 6 Torr)
• 密度：
  0.892±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：

  (S)-(1-ⁿbutylpyrrolidin-2-yl)methanamine 以 乙醇 为溶剂， 反应 30.0h， 生成 (S)-2-{N-benzyl-N-[(1-ⁿbutylpyrrolidin-2-yl)methyl]aminomethyl}-4,6-di-tert-butylphenol
  参考文献：
  名称：

  探索手性氨基酚盐锌配合物的非对映选择性合成中的立体效应和外消旋丙交酯的立体选择性开环聚合

  摘要：

  一系列三齿的手性氨基酚前配体和相应的锌络合物，LZnX（L =（的小号）-2 - {[（1-R 4 -2-吡咯烷基）CH 2 N（R 3） - ] CH 2 } -6--R 1 -4-R 2 -C 6 H 2 O，X = N（SiMe 3）2，R 3 = n Bu，R 4 = Bn：R 1 = R 2 = Cl（1），R 1 = R 2 = Me（2），R 1 = R 2 = t Bu（3）; X = N（SiMe 3）2，R 1 =三苯甲基，R 2 = Me：R 3 =正辛基，R 4 = Bn（4），R 3 = Bn，R 4 = Bn（5），R 3 = n Bu，R 4＝萘-1-基甲基（6），R 3＝n Bu，R 4＝i Pr（7）；R 1 = R 2 =枯基，R 3 = Et，R 4 = Bn：X = N（SiMe3）2（8），已合成X = O t Bu（9），X = Et（10），X

  DOI：

  10.1021/acs.inorgchem.6b00378
• 作为产物：
  描述：

  2-aminomethyl-1-butyl pyrrolidine 生成 (S)-(1-ⁿbutylpyrrolidin-2-yl)methanamine
  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。
• Stereoselective Polymerization of <i>rac</i>-Lactide Catalyzed by Zinc Complexes with Tetradentate Aminophenolate Ligands in Different Coordination Patterns: Kinetics and Mechanism
  作者：Yang Yang、Haobing Wang、Haiyan Ma

  DOI：10.1021/acs.inorgchem.5b00558

  日期：2015.6.15

  versatile coordination patterns of these complexes in the solid state were further confirmed by X-ray diffraction studies on complexes 2, 3, 5, and 7. In complex 3, the N,N-diisopropylamino group on the pendant side arm does not coordinate to the metal center; only the remaining three donors of the aminophenolate ligand and the silylamido group interact with the zinc center. By contrast, in complexes 2, 5

  一系列带有[NNNO]型四齿氨基酚盐配体的单体锌硅烷基铝配合物，LZnN（SiMe 3）2 [L = （（R 2）ArCH 2 N [（CH 2）2 R 2）CH 2（4- R 4 -6-R 3）C 6 H 2 O-}，R 1＝ NMe 2，R 2＝ N i Pr 2，R 3＝ R 4＝ Cl（1），R 3＝ R 4＝枯基（3））; [R 1＝ NMe 2，R 2＝ NEt 2，R 3＝ R 4＝枯基（2），R 3＝ CPh 3，R 4＝ Me（4）；R 1＝ NEt 2，R 2＝ NEt 2，R 3＝ CPh 3，R 4＝ Me（5）；R 1＝ NMe 2，R 2＝（S）-1-丁基吡咯烷-2-基，R 3＝ R 4＝枯基（6），R 3。通过Zn [N（SiMe 3）2 ] 2和1当量的相应氨基酚的反应合成了＝ CPh 3，R 4＝ Me（7）] 。在固态下这些复合物的性质的单体和通用协调
• Highly diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide
  作者：Haobing Wang、Haiyan Ma

  DOI：10.1039/c3cc44980g

  日期：——

  An enantiopure zinc complex supported by an aminophenolate ligand with multiple stereogenic centers has been diastereoselectively synthesized via the variation of the ortho-substituent of a phenoxy moiety and the N-alkyl group of a chiral pyrrolidinyl ring in the ligand framework, which displays high isoselectivity in the polymerization of rac-lactide.

  通过改变配体框架中一个苯氧基的正位取代基和一个手性吡咯烷基环的 N-烷基，我们非对映地合成了一种由具有多个立体中心的氨基苯酚配体支持的不纯锌配合物，该配合物在 rac-lactide 的聚合过程中显示出很高的等选择性。
• 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：
• Diastereoselective synthesis of chiral aminophenolate magnesium complexes and their application in the stereoselective polymerization of rac-lactide and rac-β-butyrolactone
  作者：Haobing Wang、Jianshuang Guo、Yang Yang、Haiyan Ma

  DOI：10.1039/c6dt01126h

  日期：——

  stereoselectivity of chiral magnesium complexes gradually changed from isoselective-biased (Pm = 0.67) to heteroselective-enriched (Pr = 0.81) via a stepwise adjustment of the substituents of the ligand framework. It was noted that, as the rare reported active magnesium initiator for the ROP of rac-BBL, complexes 3–9 can efficiently initiate the ring-opening polymerization of rac-BBL in a controlled

  合成了一系列由手性氨基酚酸酯配体支撑的甲硅烷基铝镁配合物，探讨了它们对rac-丙交酯（LA）和rac -β-丁内酯（BBL）的开环聚合的催化行为。镁[N（森达的反应3）2 ] 2与手性三齿氨基苯酚大号1-10 ħ [L =（小号） - [（1-R 4，2-吡咯烷基）CH 2 N（R 3） - ] } CH 2 - （6-R 1 -4-R 2）-C 6 H ^ 2 ö -]在甲苯中以1：1的摩尔比得到手性氨基酚盐镁硅氢酰胺基配合物L 1-10 MgN（SiMe 3）2为对映体纯化合物或非对映体。通过X射线分析确定，非对映异构体混合物的结构a和b采用S C S N R N R Mg - a和S C S N S N S Mg - b的构型， 分别。已经发现，这些镁配合物中的大多数充当rac -LA的开环聚合的高活性引发剂。此外，通过逐步调节配体骨架的取代基，手性镁配合物的立体选择性从等选择偏（P