(2S)-2-(甲氧基甲基)吡咯烷盐酸盐 | 95312-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S)-2-(甲氧基甲基)吡咯烷盐酸盐
• 英文名称: (S)-prolinol methyl ether hydrochloride
• 英文别名: (2S)-methoxymethylpyrrolidine hydrochloride；(S)-2-(methoxymethyl)pyrrolidine hydrochloride；(S)-2-Methoxymethyl-pyrrolidine hydrochloride；(2S)-2-(methoxymethyl)pyrrolidine;hydrochloride
• CAS: 95312-81-5
• 化学式: C₆H₁₃NO*ClH
• 分子量: 151.636
• InChiKey: QTMPYFZNWHQZAZ-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-(甲氧基甲基)吡咯烷盐酸盐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.33h， 生成 7-isopropoxy-5,6-dimethoxy-2-{{4-{{[(S)-2-(methoxymethyl)-1-pyrrolidinyl]carbonyl}oxy}phenyl}thio}-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Carbamate Prodrugs of a Phenolic Compound

  摘要：

  酚类化合物1的一系列氨基甲酸酯被制备并作为前药在体内进行了评估。每种氨基甲酸酯被口服给予大鼠，并随着时间的推移测量母体化合物1的血浆浓度。我们从1的AUC值和血浆中无氨基甲酸酯存在这两方面来判断哪种氨基甲酸酯适合作为1的前药。口服给予2b后1的AUC值大约是直接给予1的40倍，且2b向1的生物转化非常出色。总体而言，双取代氨基甲酸酯导致1的血浆浓度高于单取代氨基甲酸酯。然而双取代氨基甲酸酯几乎总是被检测到在血浆中存在。因此，我们发现乙氨基甲酸酯衍生物2b在这一系列中显示出最佳的前药特性。

  DOI：

  10.1248/cpb.55.328
• 作为产物：
  描述：

  (S)-tert-butyl 2-(methoxymethyl)pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2S)-2-(甲氧基甲基)吡咯烷盐酸盐
  参考文献：
  名称：

  CHEMOKINE RECEPTOR MODULATORS AND USES THEREOF

  摘要：

  披露的内容包括但不限于，用于调节趋化因子受体活性的化合物及其使用方法。

  公开号：

  US20180072743A1

文献信息

• Enantioselective Vicinal Bis-Acylation of Olefins
  作者：Léon Ghosez、Florence Mahuteau-Betzer、Christophe Genicot、Adelina Vallribera、Jean-François Cordier

  DOI：10.1002/1521-3765(20020802)8:15<3411::aid-chem3411>3.0.co;2-a

  日期：2002.8.2

  A two-step sequence for the asymmetric vicinal acylation of olefins by a [2+2+1] strategy is reported. The key reaction is a [2+2] cycloaddition of an olefin to a chiral keteniminium salt derived from N-tosylsarcosinamide. This is followed by a regioselective Baeyer-Villiger oxidation of the resulting cyclobutanone to yield a lactol derivative that is equivalent to the product of addition of a carboxyl

  报道了通过[2 + 2 + 1]策略进行烯烃不对称邻位酰化的两步序列。关键反应是烯烃与衍生自N-甲苯磺酰基肌氨酸酰胺的手性酮亚胺盐的[2 + 2]环加成反应。随后是所得环丁酮的区域选择性的Baeyer-Villiger氧化，以生成丙三醇衍生物，其等同于将羧基和羰基加成至烯烃。衍生自脯氨醇甲基醚和2,5-二甲基吡咯烷的N-甲苯磺酰基肌氨酸酰胺具有最佳的收率和非对映选择性。五元和六元环烯烃仅产生预期的顺式产物。在具有七元和八元环和顺式1，2-二取代的无环烯烃的情况下，观察到顺式部分或完全差向异构化为反式加合物。除末端烯烃外，表面选择性总体上良好。氧化步骤以高收率进行，得到结晶化合物，其通常可以通过简单的重结晶以对映纯形式获得。
• Simplified Analogues of Immucillin-G Retain Potent Human Purine Nucleoside Phosphorylase Inhibitory Activity
  作者：Teresa Semeraro、Andrea Lossani、Maurizio Botta、Chiara Ghiron、Reinaldo Alvarez、Fabrizio Manetti、Claudia Mugnaini、Silvia Valensin、Federico Focher、Federico Corelli

  DOI：10.1021/jm060547+

  日期：2006.10.1

  A set of deazaguanine derivatives 1-3 targeting human purine nucleoside phosphorylase (hPNP) have been designed and synthesized. The new compounds are characterized by the presence of a structurally simplified "azasugar" motif to be more easily accessible by chemical synthesis than previous inhibitors. In the enzymatic assays, some of the new derivatives proved to be able to inhibit hPNP at low nanomolar concentration, thereby showing the same inhibitory potency in vitro as immucillin-H (IMH). Molecular docking experiments revealed a binding mode to hPNP essentially identical to that of IMH. As a result, the lower in vivo activity exhibited by 1d, compared with that exhibited by IMH, might be ascribed to differences in the pharmacokinetic, rather than pharmacodynamic, profile between these compounds. Derivatives 1a, 1d, and 2c emerged as the most active compounds within this new set and may represent interesting leads in the search for novel hPNP inhibitors.
• (S)-(&amp;#8722;)-1-AMINO-2-METHOXYMETHYLPYRROLIDINE (SAMP) AND (R)-(+)-1-AMINO-2-METHOXYMETHYLPYRROLIDINE (RAMP), VERSATILE CHIRAL AUXILIARIES
  作者：Enders, Dieter、Fey, Peter、Kipphardt, Helmut

  DOI：10.15227/orgsyn.065.0173

  日期：——
• 2-ETHYLAMINE SUBSTITUTED BENZOFURAN AND BENZOTHIOPHENE COMPOSITIONS FOR MENTAL DISORDERS OR ENHANCEMENT
  申请人：[en]TACTOGEN INC

  公开号：WO2024108179A2

  公开（公告）日：2024-05-23

  Pharmaceutically active 2-ethylamine substituted benzofuran and benzothiophene compositions are provided for the treatment of mental disorders or for mental enhancement, including for entactogenic therapy. The present invention also includes 2-ethylamine substituted benzofuran and benzothiophene compounds, compositions, and methods for generally modulating central nervous system activity and treating central nervous system disorders.
• Synthesis and Evaluation of Carbamate Prodrugs of a Phenolic Compound
  作者：Yasushi Igarashi、Erika Yanagisawa、Toshihiro Ohshima、Shuichi Takeda、Masaki Aburada、Ken-ichi Miyamoto

  DOI：10.1248/cpb.55.328

  日期：——

  A series of carbamates of the phenolic compound 1 were prepared and evaluated in vivo as its prodrug. Each carbamate was orally administered to rats, and plasma concentrations of the parent compound 1 were measured with the passage of time. We judged which carbamate was suitable for the prodrug of 1 from both the AUC value of 1 and absence of the carbamate in plasma. The AUC value of 1 after oral administration of 2b was approximately 40-fold higher than that for an administration of 1, and the bioconversion from 2b to 1 was excellent. As a whole, di-substituted carbamates resulted in higher plasma concentrations of 1 than did mono-substituted ones. However di-substituted carbamates were almost always detected in plasma. As a result, we found that the ethycarbamoyl derivative 2b demonstrates the best prodrug property in this series.

  酚类化合物1的一系列氨基甲酸酯被制备并作为前药在体内进行了评估。每种氨基甲酸酯被口服给予大鼠，并随着时间的推移测量母体化合物1的血浆浓度。我们从1的AUC值和血浆中无氨基甲酸酯存在这两方面来判断哪种氨基甲酸酯适合作为1的前药。口服给予2b后1的AUC值大约是直接给予1的40倍，且2b向1的生物转化非常出色。总体而言，双取代氨基甲酸酯导致1的血浆浓度高于单取代氨基甲酸酯。然而双取代氨基甲酸酯几乎总是被检测到在血浆中存在。因此，我们发现乙氨基甲酸酯衍生物2b在这一系列中显示出最佳的前药特性。