(S)-N-苄基吡咯-3-甲醇对甲苯磺酸酯 | 116183-79-0

• 物质功能分类: 化学试剂 - 有机试剂 - 甲苯磺酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-N-苄基吡咯-3-甲醇对甲苯磺酸酯
• 中文别名: (S)-1-苄基-3-[(对甲苯基磺酰基)氧基]吡咯烷；(S)-N-苄基吡咯-3-甲醇对甲基苯磺酸酯
• 英文名称: (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine
• 英文别名: 3(S)-(4-methylphenylsulfonyloxy)-1-phenylmethyl pyrrolidine；(S)-toluene-4-sulfonic acid 1-benzyl-pyrrolidin-3-yl ester；toluene-4-sulfonic acid (S)-1-benzylpyrrolidin-3-yl ester；(S)-1-Benzyl-3-(p-toluenesulfonyloxy)pyrrolidine；3S-1-Benzyl-3-(p-toluenesulfonyloxy)pyrrolidine；(3S)-3-[(4-tolylsulfonyl)oxy]-1-(phenylmethyl)pyrrolidine；(S)-1-Benzyl-3-[(P-tolylsulfonyl)oxy]pyrrolidine；[(3S)-1-benzylpyrrolidin-3-yl] 4-methylbenzenesulfonate
• CAS: 116183-79-0
• 化学式: C₁₈H₂₁NO₃S
• 分子量: 331.436
• InChiKey: DFFINYKUAYHRBO-KRWDZBQOSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  466.3±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-苄基吡咯-3-甲醇对甲苯磺酸酯 在 吡啶 、 sodium azide 、 sodium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 (3S)-3-azido-1-(phenylmethyl)pyrrolidine
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028
• 作为产物：
  描述：

  N-苄基-3-吡咯烷醇 在 吡啶 、 三乙烯二胺 、 Bacillus licheniformis protease Alcalase 作用下， 以 aq. phosphate buffer 、 甲基叔丁基醚 为溶剂， 反应 15.0h， 生成 (S)-N-苄基吡咯-3-甲醇对甲苯磺酸酯
  参考文献：
  名称：

  Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution

  摘要：

  The synthesis of both enantiomers of N-benzyl-3-hydroxypyrrolidine and N-benzyl-3-hydroxypiperidine via enzymatic kinetic resolution of the corresponding racemic esters is described. Various commercially available hydrolases were studied as biocatalysts in native and immobilized form. The best results were obtained with lipases PS, AK, CAL-B and with protease Alcalase, which were active and selective for the kinetic resolutions of racemic esters (E > 100). Under optimized reaction conditions, highly enantiomerically enriched (up to 99.5% ee) resolution products were obtained. Lipase and protease showed opposite enantiopreference on the esters, allowing the preparation of both enantiomers of the target compounds. Semi-continuous reactions in column reactors with immobilized biocatalysts were also performed with high enantioselectivities. Inversion of the configuration at C(3) of N-benzyl-3-hydroxypyrrolidine was quantitatively effected in a short number of steps. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.04.009

文献信息

• PTERIDINONE COMPOUNDS AND USES THEREOF
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20190322673A1

  公开（公告）日：2019-10-24

  The present invention provides compounds of Formula I, or pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof, and methods of use thereof for treating cellular proliferative disorders (e.g., cancer).

  本发明提供了式I的化合物或其药学上可接受的盐，以及用于治疗细胞增殖性疾病（例如癌症）的药物组合物和使用方法。
• [EN] SUBSTITUTED 4-AMINO-1-BENZYLPIPERIDINE COMPOUNDS<br/>[FR] COMPOSES DE 4-AMINO-1-BENZYLPIPERIDINE SUBSTITUES
  申请人：THERAVANCE INC

  公开号：WO2005007645A1

  公开（公告）日：2005-01-27

  This invention provides 4-amino-1-benzylpiperidine and related compounds and pharmaceutically acceptable salts thereof which are useful as muscarinic receptor antagonists. This invention also provides pharmaceutical compositions containing such compounds; processes and intermediates useful for preparing such compounds; and methods for treating disease conditions mediated by muscarinic receptors, such as overactive bladder, irritable bowel syndrome, asthma and chronic obstructive pulmonary disease, using such compounds.

  这项发明提供了4-氨基-1-苄基哌啶及其相关化合物和药学上可接受的盐，这些化合物可用作毒蕈碱受体拮抗剂。该发明还提供了含有这些化合物的药物组合物；用于制备这些化合物的有用中间体和过程；以及使用这些化合物治疗由毒蕈碱受体介导的疾病状况的方法，如膀胱过度活跃、肠易激综合征、哮喘和慢性阻塞性肺病。
• Exploring Derivatives of Quinazoline Alkaloid <scp>l</scp>-Vasicine as Cap Groups in the Design and Biological Mechanistic Evaluation of Novel Antitumor Histone Deacetylase Inhibitors
  作者：Mudassier Ahmad、Mushtaq A. Aga、Javeed Ahmad Bhat、Brijesh Kumar、Abdul Rouf、Neena Capalash、Mubashir Javeed Mintoo、Ashok Kumar、Priya Mahajan、Dilip Manikrao Mondhe、Amit Nargotra、Parduman Raj Sharma、Mohmmad Afzal Zargar、Ram A. Vishwakarma、Bhahwal Ali Shah、Subhash Chandra Taneja、Abid Hamid

  DOI：10.1021/acs.jmedchem.7b00322

  日期：2017.4.27

  inhibited cancer cell growth and induced cell death by various mechanisms. However, 4a was found to induce cell death independent of ROS generation, and unlike many natural product based HDAC inhibitors, 4a was found to be nontoxic under in vivo conditions. Importantly, we for the first time report the possibility of using a 3-hydroxypyrrolidine cap for the synthesis of HDAC inhibitors with good potency

  1- Vasicine是一种喹唑啉生物碱，具有电子致密环，并且在其结构中具有其他功能。利用基于计算机模拟研究的靶向定向合成（TOS），合成了具有显着对接分数的分子，其中包含1- vasicine的不同衍生物作为帽。有趣的是，发现一个分子，即4a，它含有3-羟基吡咯烷作为帽基和一个六碳长的脂肪族链作为连接基，可以抑制HDAC。图4a显示了对I类HDAC同工型的更多特异性。与癌细胞系相比，还发现4a对正常细胞系的细胞毒性较小。4a通过多种机制抑制癌细胞的生长并诱导细胞死亡。但是，发现4a可以诱导细胞死亡而与ROS的产生无关，并且与许多基于天然产物的HDAC抑制剂不同，发现4a在体内条件下是无毒的。重要的是，我们首次报道了使用3-羟基吡咯烷帽合成具有良好效力的HDAC抑制剂的可能性。
• Diphenylmethyl compounds useful as muscarinic receptor antagonists
  申请人：Mammen Mathai

  公开号：US20050203167A1

  公开（公告）日：2005-09-15

  This invention provides compounds of formula I: wherein a, b, c, e, m, n, Ar 1 , R 1 , R 2 , R 3 , R 4a , R 4b , R 5 and R 6 are as defined in the specification. The compounds of formula I are muscarinic receptor antagonists. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing such compounds and methods of using such compounds to treat pulmonary disorders.

  这项发明提供了化合物的公式I：其中a、b、c、e、m、n、Ar1、R1、R2、R3、R4a、R4b、R5和R6如规范中所定义。公式I的化合物是肌气镇静受体拮抗剂。该发明还提供了含有这些化合物的药物组合物，用于制备这些化合物的过程和中间体，以及使用这些化合物治疗肺部疾病的方法。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSES ORGANIQUES
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2005061457A1

  公开（公告）日：2005-07-07

  Novel substituted piperidines of the general formulae (I) and (II) with the substituent definitions as explained in detail in the description are described. The compounds are suitable in particular as renin inhibitors and are highly potent.

  描述了一种具有一般式(I)和(II)的新型替代哌啶化合物，其中详细说明了取代基定义。这些化合物特别适用作为肾素抑制剂，并且具有很高的效力。