(S)-2-(苯氧基甲基)吡咯烷 | 174213-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-2-(苯氧基甲基)吡咯烷
• 英文名称: (S)-2-(phenoxymethyl)pyrrolidine
• 英文别名: (2S)-2-(phenoxymethyl)pyrrolidine
• CAS: 174213-76-4
• 化学式: C₁₁H₁₅NO
• mdl: MFCD10022827
• 分子量: 177.246
• InChiKey: CVINTVJDIQIIGZ-JTQLQIEISA-N

物化性质

• 沸点：
  277.3±13.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(苯氧基甲基)吡咯烷 在 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  高效的合成，生物学评估和对基于半胱氨​​酸蛋白酶的半胱天冬酶抑制剂的对接研究。

  摘要：

  在本文中，设计，合成和评估了一系列新的基于isatin-sulphonamide的衍生物作为胱天蛋白酶抑制剂。与未取代的衍生物相比，在靛红核的C5位上含有1-（吡咯烷基）磺酰基和2-（苯氧基甲基）吡咯烷-1-基）磺酰基取代的化合物表现出更好的结果。根据caspase抑制活性的结果，与Ac-DEVD-CHO相比，化合物20d在体外显示出对caspase-3和-7的中等抑制活性（IC 50 = 0.016±0.002μM）。在研究的化合物中，鉴定出一些活性抑制剂，IC 50值在2.33–116.91μM之间。化合物20d的活性通过分子建模研究使之合理化，该研究展示了N-苯基乙酰胺取代的额外范德华相互作用以及有效的T形π-π和π-阳离子相互作用。具有良好的半胱天冬酶抑制活性的化合物20d的引入将有助于研究人员寻找更有效的药物。

  DOI：

  10.1080/14756366.2020.1809388
• 作为产物：
  描述：

  L-脯氨醇 在 吡啶 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 (S)-2-(苯氧基甲基)吡咯烷
  参考文献：
  名称：

  5-Pyrrolidinylsulfonyl Isatins as a Potential Tool for the Molecular Imaging of Caspases in Apoptosis

  摘要：

  Caspases are the unique enzymes responsible for the execution of the cell death program and may represent an exclusive target for the specific molecular imaging of apoptosis in vivo. 5-Pyrrolidinylsulfonyl isatins represent potent nonpeptidyl caspase inhibitors that may be suitable for the development of caspase binding radioligands ( CBRs). ( S)-5-[ 1-(2-Methoxymethylpyrrolidinyl) sulfonyl] isatin ( 7) served as a lead compound for modification of its N-1-position. Corresponding pairs of N-1-substituted 2-methoxymethyl- and 2-phenoxymethylpyrrolidinyl derivatives were examined in vitro by biochemical caspase inhibition assays. All target compounds possess high in vitro caspase inhibtion potencies in the nanomolar to subnanomolar range for caspase-3 ( K-i = 0.2- 56.1 nM). As shown for compound ( S)-1-( 4-(2-fluoroethoxy) benzyl)-5-[ 1( 2-methoxymethylpyrrolidinyl) sulfonyl] isatin ( 35), the class of N-1-substituted 5-pyrrolidinylsulfonyl isatins competitively inhibits caspase-3. All caspase inhibitors show selectivity for the effector caspases-3 and -7 in vitro. The 2-methoxymethylpyrrolidinyl versions of the isatins appear to possess superior caspase inhibition potencies in cellular apoptosis inhibition assays compared with the 2-phenoxymethylpyrrolidinyl inhibitors.

  DOI：

  10.1021/jm051217c

文献信息

• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Pyrimidoindolones and methods for using same
  申请人：Dollings Jeffrey Paul

  公开号：US20050250798A1

  公开（公告）日：2005-11-10

  Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.

  揭示了一种新型的嘧啶吲哚酮化合物。还揭示了使用这些嘧啶吲哚酮化合物的方法，以及包含这些化合物的组合物在治疗和/或预防与炎症、神经退行性疾病、骨关节炎和细胞凋亡相关的疾病和其他情况中的应用。
• Synthesis of Optically Active N-(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)
  作者：Udo Nubbemeyer、Jonas Donges、Sandra Hofmann、Johannes C. Walter、Julia Reichertz、Moritz Brüggemann、Andrea Frank

  DOI：10.1055/s-0037-1610770

  日期：2021.8

  (S)-configured N-propargylprolinol ethers, coupling delivered N-(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured

  从5-甲基己醛和（S）-构型的N-炔丙基脯氨醇醚开始，偶联递送作为C4非对映异构体的混合物的N-（4-羟基壬-2-炔基）脯氨醇衍生物。引入（R）-扁桃酸酯衍生物并随后进行HPLC分离后，差向异构体的拆分成功。或者，适当的氧化得到相应的炔基酮。Midland试剂控制的非对映选择性还原得到定义的构型的炔丙醇，具有高选择性。烯丙醇的LiAlH 4还原和Mosher分析可阐明结构。适当保护的产物用作对映选择性链霉菌的关键中间体 γ-丁内酯信号分子的全合成。
• [EN] AMIDO-THIOPHENE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS AMIDO-THIOPHÈNE ET LEUR UTILISATION
  申请人：UNIV EDINBURGH

  公开号：WO2009112845A1

  公开（公告）日：2009-09-17

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain amido-thiophene compounds that, inter alia, inhibit 11 β-hydroxysteroid dehydrogenase type 1 (11 β-HSD1 ). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 11 β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11 β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc.

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些酰胺-噻吩化合物，其中包括抑制11β-羟基类固醇脱氢酶1（11β-HSD1）的作用。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物和组合物，在体内和体外，抑制11β-羟基类固醇脱氢酶1；治疗通过抑制11β-羟基类固醇脱氢酶1而得到改善的疾病；治疗代谢综合征，其中包括糖尿病和肥胖等疾病，以及相关疾病，包括胰岛素抵抗、高血压、脂质紊乱和心血管疾病，如缺血性（冠状）心脏病；治疗中枢神经系统疾病，如轻度认知障碍和早期痴呆，包括阿尔茨海默病等。
• Caspases and apoptosis
  申请人：SmithKline Beecham Corporation

  公开号：US06514992B1

  公开（公告）日：2003-02-04

  The present invention is to novel compounds of Formula (I), their pharmaceutical compositions, and to the novel inhibition of Caspases for use in the treatment of apoptosis, and disease states caused by excessive or inappropriate cell death.

  本发明涉及式（I）的新化合物，它们的药物组合物，以及用于治疗凋亡和由过度或不恰当的细胞死亡引起的疾病状态的新的Caspases抑制方法。