(S)-N-butylprolinamide | 128843-29-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-butylprolinamide
• 英文别名: 1-ⁿbutylprolinamide；(S)-1-Butylpyrrolidine-2-carboxamide；(2S)-1-butylpyrrolidine-2-carboxamide
• CAS: 128843-29-8
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: DUWFKLLOEYCHRL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-butylprolinamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(1-ⁿbutylpyrrolidin-2-yl)methanamine
  参考文献：
  名称：

  Highly diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide

  摘要：

  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。

  DOI：

  10.1039/c3cc44980g
• 作为产物：
  描述：

  正溴丁烷 、 L-脯氨酰胺 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-N-butylprolinamide
  参考文献：
  名称：

  Highly diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide

  摘要：

  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。

  DOI：

  10.1039/c3cc44980g

文献信息

• Exploring Steric Effects in Diastereoselective Synthesis of Chiral Aminophenolate Zinc Complexes and Stereoselective Ring-Opening Polymerization of <i>rac</i>-Lactide
  作者：Haobing Wang、Yang Yang、Haiyan Ma

  DOI：10.1021/acs.inorgchem.6b00378

  日期：2016.8.1

  loss of the stereoselectivity, whereas the decrease of the steric bulkiness of the X group results in a reverse of the diastereoselectivity, but shows no influence on the stereoselectivity. There is probably no direct relationship between the diastereoselectivity in complex synthesis and the stereoselectivity of the complex toward the ROP of rac-LA. The stereocontrol of these complexes might largely

  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
• METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE
  申请人：API CORPORATION

  公开号：US20140127762A1

  公开（公告）日：2014-05-08

  The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.

  本发明旨在提供一种工业方法，以在温和条件下通过少量步骤从非环状酮化合物中生产光学活性α-取代脯氨酸的方法。本发明涉及一种光学活性α-取代脯氨酸（4）和/或光学活性α-取代脯氨酰胺（5）的生产方法，包括以下步骤：(a)将非环状酮化合物（1）与氨、铵盐、一级胺和一级胺盐和氰化试剂中的至少一种反应，得到环状含氮化合物（2）；(b)使环状含氮化合物（2）水合，得到α-取代脯氨酰胺（3）；(c)通过(d)酶解水解、(e)对映异构盐形成的分离和/或(f)柱层析分离中的一种或多种方法来分离α-取代脯氨酰胺（3）。
• N-Fluoroalkylated and N-alkylated analogs of the dopaminergic D-2 receptor antagonist raclopride
  作者：G. S. Lannoye、Stephen M. Moerlein、D. Parkinson、M. J. Welch

  DOI：10.1021/jm00171a017

  日期：1990.9

  A series of raclopride [(S)-2-[(3,5-dichloro-6-methoxy-2- hydroxybenzamido)methyl]-1-ethylpyrrolidine] derivatives bearing pyrrolidino N-fluoroalkyl or -alkyl substituents were synthesized and evaluated as potential dopaminergic receptor-based positron tomography radiopharmaceuticals. Radiosynthetic procedures for producing the corresponding N-[18F]fluoroalkylated analogues of raclopride from 18F- (beta+, t1/2 = 110 min) in high specific activity were also developed. In vitro binding assays using competitive displacement of [3H]spiperone from primate caudate tissue indicated that the N-alkylated analogues of raclopride had Ki values of 5-40 nM, whereas the corresponding values for analogous N-fluoroalkylated derivatives ranged from 90-160 nM. The relatively low D-2 binding affinity of these fluorinated salicylamides was corroborated by in vivo tissue biodistribution results in rodents. On the basis of structure-binding correlations, the impact of intramolecular hydrogen bonding, ligand basicity, and steric bulk on the affinity of the benzamides for D-2 receptor binding are discussed. Strategies are presented for the development of alternative fluorinated salicylamides that are both receptor active and metabolically stable.
• Amino acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0346847B1

  公开（公告）日：1994-05-11
• LANNEYE, G. S.;MOERLEIN, S. M.;PARKINSON, D.;WELCH, M. J., J. MED. CHEM., 33,(1990) N, C. 2430-2437
  作者：LANNEYE, G. S.、MOERLEIN, S. M.、PARKINSON, D.、WELCH, M. J.

  DOI：——

  日期：——