1-哌啶基[(2S)-2-吡咯烷基]甲酮 | 65921-40-6

• 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
• 中文名称: 1-哌啶基[(2S)-2-吡咯烷基]甲酮
• 英文名称: (S)-N-Prolylpiperidin
• 英文别名: piperidin-1-yl(pyrrolidin-2-yl)methanone；N-(L-Prolyl)-piperidin；(S)-piperidin-1-yl(pyrrolidin-2-yl)methanone；piperidin-1-yl-[(2S)-pyrrolidin-2-yl]methanone
• CAS: 65921-40-6
• 化学式: C₁₀H₁₈N₂O
• mdl: MFCD09810531
• 分子量: 182.266
• InChiKey: VTWSMIPLWRXVEQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-哌啶基[(2S)-2-吡咯烷基]甲酮 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-1-Ethyl-2-<(piperidin-1-yl)methyl>pyrrolidine
  参考文献：
  名称：

  通过使用手性促进剂，使乙酸酯和醛的非手性烯酮甲硅烷基缩醛之间的不对称醛醇缩合反应

  摘要：

  通过使用手性促进剂，手性二胺配位的三氟甲磺酸锡（II）（三氟甲磺酸锡（II））和三丁基氟化锡。讨论了该新启动子的结构和当前不对称醛醇型反应的机理。

  DOI：

  10.1016/s0040-4020(01)85587-3
• 作为产物：
  描述：

  (S)-2-(piperidine-1'-carbonyl)pyrrolidinium bromide 在 sodium carbonate 作用下， 以 三氯乙烷 为溶剂， 生成 1-哌啶基[(2S)-2-吡咯烷基]甲酮
  参考文献：
  名称：

  Chiral amine catalyzed enantio- and diastereoselective Michael reaction in brine

  摘要：

  Simple pyrrolidine-based chiral amines were synthesized and used for the Michael addition of different ketones to a variety of nitro-olefins in brine. The effect of different surfactants and acids on the yields and stereochemical outcome of the Michael adducts was studied in detail. Chiral amine 1g was found to catalyze the formation of Michael adducts with high enantioselectivity (up to >99%), diastereoselectivity [up to 98:2 (syn:anti)] and yield (up to 94%). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.026

文献信息

• Asymmetric Trasformation of Symmetrical Epoxides to Allylic Alcohols by Lithium (<i>S</i>)-2-(<i>N</i>,<i>N</i>-Disubstituted aminomethyl)pyrrolidide
  作者：Masatoshi Asami

  DOI：10.1246/bcsj.63.721

  日期：1990.3

  Enantioselective deprotonation of symmetrical epoxides was studied by using chiral lithium amide, prepared from (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine and butyllithium. Chiral allylic alcohols were obtained with moderate to high enantiomeric excesses (ee’s) (41–92% ee) from several cyclic and acyclic epoxides employing lithium (S)-2-(1-pyrrolidinylmethyl)pyrrolidide in tetrahydrofuran (THF) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

  使用由(S)-2-(N,N-二取代氨基甲基)吡咯烷和丁基锂制备的手性锂胺，研究了对称环氧化物的对映选择性去质子化反应。通过在四氢呋喃（THF）中采用锂(S)-2-(1-吡咯啉甲基)吡咯化锂并加入1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）的条件，从若干环状和非环状环氧化物中获得了具有中等至高度对映体过剩（ee's）（41-92% ee）的手性烯丙醇。
• Highly Regio- and Enantioselective Organocatalytic Conjugate Addition of Alkyl Methyl Ketones to a β-Silylmethylene Malonate
  作者：Raghunath Chowdhury、Sunil K. Ghosh

  DOI：10.1021/ol900803n

  日期：2009.8.6

  (S)-N-(2-Pyrrolidinylmethyl)pyrrolidine/trifluoroacetic acid (3:1) combination catalyzed the direct addition of alkyl methyl ketones to β-dimethyl(phenyl)silylmethylene malonate at the methyl terminal with high yield and excellent regio- and enantioselectivity. The silyl group played crucial roles in regioselection and substrate reactivity.

  （S）-N-（2-吡咯烷基甲基）吡咯烷/三氟乙酸（3：1）的组合催化烷基甲基酮直接加到β-二甲基（苯基）甲硅烷基亚甲基丙二酸酯的甲基末端上，具有高产率和良好的区域选择性。对映选择性。甲硅烷基在区域选择和底物反应性中起关键作用。
• Synthesis and Catalytic Activities of (<i>S</i>)-1-formylpyrrolidine-2-carboxylic Acid Derivatives for the Enantioselective Reductions of Both a Ketone and a Ketimine
  作者：Zhenfei Chen、Anjiang Zhang、Lixue Zhang、Jing Zhang、Xinxiang Lei

  DOI：10.3184/030823408x318433

  日期：2008.5

  as chiral organocatalysts in the asymmetric reduction of both ketone 2 and ketimine 3. These organic activators afforded good to moderate enantioselectivities in the asymmetric reductions of both the ketone and the ketimine. Among them, organic activator 6h displayed the best efficiency, affording a 84% yield and 41% ee in the reduction of the ketone and 75% yield and 52% ee in the reduction of the ketimine

  一系列 (S)-1-甲酰基吡咯烷-2-羧酸衍生物 (6a-t) 已被合成并作为手性有机催化剂用于酮 2 和酮亚胺 3 的不对称还原。这些有机活化剂提供了良好到中等的对映选择性酮和酮亚胺的不对称还原。其中，有机活化剂6h显示出最佳的效率，在酮的还原中提供了84％的收率和41％的ee，在酮亚胺的还原中提供了75％的收率和52％的ee。
• Selective reduction of secondary amides to amines in the presence of tertiary amides
  作者：Byung H. Lee、Michael F. Clothier

  DOI：10.1016/s0040-4039(98)02509-x

  日期：1999.1

  Secondary amides activated with a Cbz group can be reduced to their corresponding hemiaminals using lithium borohydride. Hydrogenation then removes the Cbz and hydroxyl groups to produce the related amine. Tertiary amides are not affected.

  可以使用硼氢化锂将被Cbz基团激活的仲酰胺还原为相应的半缩醛。然后氢化除去Cbz和羟基以产生相关的胺。叔酰胺不受影响。
• Novel CD40:CD154 binding interruptor compounds and use thereof to treat immunological complications
  申请人：Zheng Zhongli

  公开号：US20070249682A1

  公开（公告）日：2007-10-25

  The present invention relates to novel CD40:CD154 binding interrupter compounds and use of these compounds and pharmaceutical compositions comprising them, to treat conditions associated with inappropriate CD154 activation in a subject. Specifically, this invention provides compounds which are identified by screening a library of small molecules for those that are capable of specifically binding CD154 and interrupting CD40:CD154 interaction.

  本发明涉及新型CD40：CD154结合中断化合物的使用以及包含这些化合物的制药组合物，用于治疗与主体中不适当的CD154激活有关的疾病。具体而言，本发明提供了通过筛选小分子库以鉴定能够特异性结合CD154并中断CD40：CD154相互作用的化合物。