(R)-2-Methylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 785825-41-4

• 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: (R)-2-Methylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: (R)-1-Boc-N-methylpyrrolidine-2-carboxamide；tert-butyl (2R)-2-(methylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 785825-41-4
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: JTLUSFVWHVIZGT-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-Methylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 硼烷四氢呋喃络合物 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 2-furan-2-yl-N⁵-methyl-N⁵-pyrrolidin-2-ylmethyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine
  参考文献：
  名称：

  Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]triazine as Potent and Selective Adenosine A_2a Receptor Antagonists

  摘要：

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been demonstrated to be potent and selective adenosine A(2a) receptor antagonists with oral activity in rodent models of Parkinson's disease. We have replaced the piperazinyl group with a variety of linear, monocyclic, and bicyclic diamines. Of these diamines, (R)-2-(aminomethyl)pyrrolidine is a particularly potent and selective replacement for the piperazinyl group. With this diamine component, we have been able to prepare numerous analogues with low nanomolar affinity toward the A(2a) receptor and good selectivity with respect to the A(1) receptor (> 200-fold in some cases). Selected analogues from this series of [1,2,4]triazolo[1,5-a][1,3,5]triazine have now been shown to be orally active in the mouse catalepsy model.

  DOI：

  10.1021/jm0498396
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-D-proline 、 甲胺 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以100%的产率得到(R)-2-Methylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  [EN] TRIAZOLO[1,5-C]PYRIMIDINES AND PYRAZOLO[1,5-C]PYRIMIDINES USEFUL AS A2A ADENOSIN E RECEPTOR ANTAGONISTS
  [FR] TRIAZOLO[1,5-C]PYRIMIDINES ET PYRAZOLO[1,5-C]PYRIMIDINES ET PROCEDES DE PREPARATION ET D'UTILISATION DE CELLES-CI

  摘要：

  公开号：

  WO2004092172A3

文献信息

• Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
  作者：Byoungmoo Kim、Alex J. Chinn、Daniel R. Fandrick、Chris H. Senanayake、Robert A. Singer、Scott J. Miller

  DOI：10.1021/jacs.6b03444

  日期：2016.6.29

  guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates

  我们报道了一类新型含胍肽作为过渡金属催化多功能配体的开发及其在通过铜催化乌尔曼交叉偶联二芳基甲烷远程去对称化中的应用。通过这些肽的设计，芳基溴和丙二酸之间的长程不对称交叉偶联（高达 93:7 er 和 76% 产率）实现了高水平的对映诱导和良好的分离产率。我们的机制研究表明，远端立体控制是通过肽的路易斯碱性C端羧酸酯与底物的远端芳烃之间的Cs桥相互作用来实现的。
• PYRIMIDINE COMPOUNDS AS INHIBITORS OF PROTEIN KINASES IKK EPSILON AND/OR TBK-1, PROCESSES FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Perrior Trevor Robert

  公开号：US20130267491A1

  公开（公告）日：2013-10-10

  C Compounds of the general formula (I) and salts thereof are useful in the treatment of diseases associated with aberrant activity of the protein kinases IKKε and/or TBK-1: in which: R 1 represents an aliphatic heterocyclyl group having 4, 5, 6 or 7 ring atoms, bonded to the phenyl group shown in formula I through a ring nitrogen atom, and optionally substituted by one or more substituents defined in the Specification; R 2 represents a phenyl or heteroaryl group which is optionally substituted by one or more substituents defined in the Specification; and each of R 3 and R 4 independently represents a hydrogen atom or a C 1-4 alkyl group.

  通式（I）的化合物及其盐在治疗与蛋白激酶IKKε和/或TBK-1的异常活性相关的疾病方面是有用的：其中：R1代表通过一个环氮原子与通式I中所示的苯基相连的具有4、5、6或7个环原子的脂肪族杂环基，可选地被本说明书中定义的一个或多个取代基取代；R2代表一个苯基或杂环基，可选地被本说明书中定义的一个或多个取代基取代；R3和R4各自独立地代表氢原子或C1-4烷基。
• [EN] TRIAZOLO[1,5-A]PYRIMIDINES AND PYRAZOLO[1,5-A]PYRIMIDINES USEFUL AS A2A ADENOSIN E RECEPTOR ANTAGONISTS<br/>[FR] TRIAZOLO[1,5-A]PYRIMIDINES ET PYRAZOLO[1,5-A]PYRIMIDINES ET PROCEDES DE PREPARATION ET D'UTILISATION DE CELLES-CI
  申请人：BIOGEN IDEC INC

  公开号：WO2004092171A3

  公开（公告）日：2005-03-31
• US8962609B2
  申请人：——

  公开号：US8962609B2

  公开（公告）日：2015-02-24