tert-butyl (R)-2-(2-bromoacetyl)pyrrolidine-1-carboxylate | 152665-80-0

• 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: tert-butyl (R)-2-(2-bromoacetyl)pyrrolidine-1-carboxylate
• 英文别名: (R)-N-tert-butoxycarbonyl-2-bromoacetylpyrrolidine；N-Boc-(R)-2-bromoacetylpyrrolidine；tert-butyl (2R)-2-(2-bromoacetyl)pyrrolidine-1-carboxylate
• CAS: 152665-80-0
• 化学式: C₁₁H₁₈BrNO₃
• 分子量: 292.173
• InChiKey: AHDOQGYAXYGUQV-MRVPVSSYSA-N

物化性质

• 沸点：
  351.4±32.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2-(2-bromoacetyl)pyrrolidine-1-carboxylate 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 丙酮 为溶剂， -20.0~20.0 ℃ 、506.66 kPa 条件下， 反应 29.0h， 生成 (2R,2'R)-2-(2'-pyrrolidinyl)-7-hydroxy-1,4-benzodioxane
  参考文献：
  名称：

  Unichiral 2-(2′-Pyrrolidinyl)-1,4-benzodioxanes: the 2R,2′S Diastereomer of the N-Methyl-7-hydroxy Analogue Is a Potent α4β2- and α6β2-Nicotinic Acetylcholine Receptor Partial Agonist

  摘要：

  A series of unichiral 7-substituted 2-(1'-methyl-2'pyrrolidinyl)-1,4-benzodioxanes were synthesized and tested for the affinity for the alpha 4 beta 2 and alpha 7 central nicotinic receptors; the 2R,2'S diastereomer of the 7-OH analogue [(R,S)-7], unique in the series, has a high alpha 4 beta 2 affinity (12nM K-i). N-Demethylation and configuration inversion of the stereocenters greatly weaken its alpha 4 beta 2 affinity, confirming that such a rigid molecule can be considered a new template for alpha 4 beta 2 ligands. Docking analysis showed how (R,S)-7 is capable of strongly and specifically interacting with the amino acidic counterpart of the alpha 4 beta 2 receptor binding site. Further pharmacological characterization demonstrated that (R,S)-7 also has a high affinity for the alpha 6 beta 2 receptor, and in vitro functional tests indicated that it is a potent alpha 4 beta 2 and alpha 6 beta 2 partial agonist, with modest affinity and potency for the alpha 3 beta 4 receptor. Comparison with varenicline, a well-known nicotinic partial agonist used as a smoking cessation aid, interestingly reveals similar nicotinoid profiles.

  DOI：

  10.1021/jm200937t
• 作为产物：
  描述：

  (R)-2-(2-二氮杂乙酰基)吡咯烷-1-羧酸叔丁酯 在 氢溴酸 作用下， 以 乙醚 、 水 为溶剂， 反应 1.5h， 生成 tert-butyl (R)-2-(2-bromoacetyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: Synthesis of all the stereoisomers and α4β2 nicotinic affinity

  摘要：

  The four stereoisomers of 2-oxazolidinone 5-substituted with 1-methyl-2-pyrrolidinyl (1), of 1,4-benzodioxane 2-substituted with the same residue (2) and of the nor-methyl analogue of this latter (2a) were synthesized as candidate nicotinoids. Of the 12 compounds, two N-methylated pyrrolidinyl-benzodioxane stereoisomers, namely those with the same relative configuration at the pyrrolidine stereocentre as (S)-nicotine, bind at alpha 4 beta 2 nicotinic acetylcholine receptor with submicromolar affinity. Consistently with the biological data, docking analysis enlightens significant differences in binding site interactions not only between 1 and 2, but also between 2 and 2a and between the stereoisomers of 2 accounting for the critical role played, in the case of the pyrrolidinyl-benzodioxanes, by the chirality of both the stereolabile and stereostable stereogenic atoms, namely the protonated tertiary nitrogen and the two asymmetric carbons. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.002

文献信息

• Arphamenine and its related compounds, a process for their preparation and their use as medicaments
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0129163A1

  公开（公告）日：1984-12-27

  The present invention relates to Arphamenine-related compounds of the formula wherein R respresents an α-amino acid residue corresponding to an α-amino acid molecule from which the a-carboxyl group has been removed, to a process for their preparation, and their use as medicaments having immunopotentiating activity.

  本发明涉及如下式的阿法米宁相关化合物 其中 R 代表与去除了 a-羧基的 α-氨基酸分子相对应的α-氨基酸残基，本发明涉及其制备方法，以及其作为具有免疫增强活性的药物的用途。
• 吲哚噻唑酮类化合物及其应用
  申请人：张所明

  公开号：CN116925066A

  公开（公告）日：2023-10-24

  本发明涉及一种式(I)所示的吲哚噻唑酮类化合物，及其药学上可接受的盐或溶剂合物或同位素变体或异构体，#imgabs0#其中，各取代基具有本申请中公开的含义。本发明的化合物能够调节AhR活性，用作AhR激动剂。
• [EN] MUSCARINIC AGONISTS<br/>[FR] AGONISTES MUSCARINIQUES
  申请人：HEPTARES THERAPEUTICS LIMTED

  公开号：WO2017021728A9

  公开（公告）日：2017-04-27
• BENZODIAZEPIN DERIVATIVES USEFUL AS CCK-RECEPTOR ANTAGONISTS
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0628033A1

  公开（公告）日：1994-12-14
• US5688943A
  申请人：——

  公开号：US5688943A

  公开（公告）日：1997-11-18