1-[(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)-pyridinone | 934698-37-0

• 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: 1-[(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)-pyridinone
• 英文别名: (3E)-3-benzylidene-1-[(1R)-1-phenylethyl]piperidin-4-one
• CAS: 934698-37-0
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: OXCOVIAXSXLVNU-NISQSXRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-[(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)-pyridinone 、 (Z)-N-hydroxy-4-chloro-benzenecarboximidoyl chloride 在 三乙胺 作用下， 以 苯 为溶剂， 以54%的产率得到(4R,5S)-3-(4-chlorophenyl)-4-phenyl-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: synthesis of enantiomerically pure spiro heterocycles

  摘要：

  The 1,3-dipolar cycloaddition of (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones to nitrile oxides proceeds chemo-, regio-, and stereoselectively affording moderate yields of enantiomerically pure spiro heterocycles comprising piperidine and isoxazoline/dioxazole rings. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.015
• 作为产物：
  描述：

  (R)-1-(1-phenylethyl)piperidin-4-one 、 苯甲醛 在 四氢吡咯 作用下， 反应 0.06h， 以58%的产率得到1-[(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)-pyridinone
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: synthesis of enantiomerically pure spiro heterocycles

  摘要：

  The 1,3-dipolar cycloaddition of (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones to nitrile oxides proceeds chemo-, regio-, and stereoselectively affording moderate yields of enantiomerically pure spiro heterocycles comprising piperidine and isoxazoline/dioxazole rings. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.015

文献信息

• 1,3-Dipolar cycloaddition of C-aryl-N-phenylnitrones to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis and antimycobacterial evaluation of enantiomerically pure spiroisoxazolidines
  作者：Raju Suresh Kumar、Subbu Perumal、Krithika Arun Shetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.09.034

  日期：2010.1

  A series of novel enantiomerically pure spiroisoxazolidines were synthesized regioselectively by the 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidenejtetrahydro-4(1H)-pyridinones. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among the twenty two compounds screened, (3S,4S,5R)-3,4-di(4-methylphenyl)-2-phenyl-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]decan-10-one (3e) was found to possess the maximum activity with MIC of 3.02 mu M, being 2.5 times more potent than the first-line anti-TB drug ethambutol. For comparison, a series of ten enantiomerically pure spirooxazolines were also screened, among which (4R,5S)-3,4-bis(4-chlorophenyl)-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one and (4R,5S)-4-(2-chlorophenyl)-3-(4-chlorophenyl)-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one were found to display maximum activity with MIC of 3.25 mu M. (C) 2009 Published by Elsevier Masson SAS.