meso-N-butyl-2,6-diphenyl-4-piperidone | 725712-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: meso-N-butyl-2,6-diphenyl-4-piperidone
• 英文别名: meso-1-butyl-2,6-diphenylpiperidin-4-one；(2R,6S)-1-butyl-2,6-diphenylpiperidin-4-one
• CAS: 725712-74-3
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: YIZIHCIBTABEJO-OYRHEFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基-4-亚氨基-利福霉素 、 meso-N-butyl-2,6-diphenyl-4-piperidone 在 乙酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以46.5%的产率得到4-deoxo-3,4-[(2r)-2-spiro(N-butyl-2,6-diphenyl-4-piperidyl)-2,5-dihydro-1H-imidazo]rifamycin S
  参考文献：
  名称：

  New rifabutin analogs: Synthesis and biological activity against Mycobacterium tuberculosis

  摘要：

  The synthesis, structure, and biological evaluation of a series of novel rifamycin derivatives, Rifastures (RFA) with potent anti-tuberculosis activity are presented. Some of these derivatives showed higher in vitro activity than rifabutin and rifampicin against not only Mycobacterium tuberculosis strains but also against MAC and Mycobacterium kansasii. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.090
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 meso-N-butyl-2,6-diphenyl-4-piperidone
  参考文献：
  名称：

  亚氨基狄尔斯-阿尔德合成中消旋-2,6-二取代-4-哌啶酮的路线

  摘要：

  的一种方便的立体选择性制备内消旋-2,6-二取代-4-哌啶酮已经通过与亚胺在铜（TFO）的催化量存在的2-氨基-1,3-丁二烯亚氨基Diels-Alder反应研制2。

  DOI：

  10.1016/j.tetlet.2004.03.195

文献信息

• Stereoselective Synthesis of <i>meso</i>- and <i>cis</i>-2,6-Diarylpiperidin-4-ones Catalyzed by <scp>l</scp>-Proline
  作者：Fernando Aznar、Ana-Belén García、Noelia Quiñones、María-Paz Cabal

  DOI：10.1055/s-2007-990814

  日期：2008.2

  A convenient stereoselective preparation of meso- and cis-2,6-diarylpiperidin-4-ones has been developed by aza-Diels-Alder reaction­ catalyzed by l-proline from simple and commercially available starting materials.

  在 l-脯氨酸的催化下，利用简单的市售起始原料，通过偶氮-Diels-Alder 反应，开发出了一种方便的立体选择性制备介-和顺-2,6-二芳基哌啶-4-酮的方法。
• Proline-Catalyzed Imino-Diels–Alder Reactions: Synthesis ofmeso-2,6-Diaryl-4-piperidones
  作者：Fernando Aznar、Ana-Belén García、María-Paz Cabal

  DOI：10.1002/adsc.200600318

  日期：2006.11

  Amine-catalyzed imino-Diels–Alder reactions of acyclic α,β-unsaturated ketones with imines have been developed. L-Proline catalyzed the in situ generation of 2-amino-1,3-butadienes to provide a stereoselective synthesis of meso-2,6-diaryl-4-piperidones in one direct step.

  已经开发了胺催化的无环α，β-不饱和酮与亚胺的亚氨基Diels-Alder反应。L-脯氨酸在一个直接步骤中催化了2-氨基-1,3-丁二烯的原位生成，从而提供了内消旋-2,6-二芳基-4-哌啶酮的立体选择性合成。
• An imino-Diels–Alder route to meso-2,6-disubstituted-4-piperidones
  作者：Ana-Belén Garcı́a、Carlos Valdés、Marı́a-Paz Cabal

  DOI：10.1016/j.tetlet.2004.03.195

  日期：2004.5

  A convenient stereoselective preparation of meso-2,6-disubstituted-4-piperidones has been developed by imino-Diels–Alder reaction of 2-amino-1,3-butadienes with imines in the presence of catalytic amount of Cu(TfO)2.

  的一种方便的立体选择性制备内消旋-2,6-二取代-4-哌啶酮已经通过与亚胺在铜（TFO）的催化量存在的2-氨基-1,3-丁二烯亚氨基Diels-Alder反应研制2。
• New rifabutin analogs: Synthesis and biological activity against Mycobacterium tuberculosis
  作者：José Barluenga、Fernando Aznar、Ana-Belén García、María-Paz Cabal、Juan J. Palacios、María-Angela Menéndez

  DOI：10.1016/j.bmcl.2006.08.090

  日期：2006.11

  The synthesis, structure, and biological evaluation of a series of novel rifamycin derivatives, Rifastures (RFA) with potent anti-tuberculosis activity are presented. Some of these derivatives showed higher in vitro activity than rifabutin and rifampicin against not only Mycobacterium tuberculosis strains but also against MAC and Mycobacterium kansasii. (c) 2006 Elsevier Ltd. All rights reserved.