(E)-3-(4-methoxybenzylidene)-1-methylpiperidin-4-one | 1131012-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-(4-methoxybenzylidene)-1-methylpiperidin-4-one
• 英文别名: 3-[(E)-(4-methoxyphenyl)methylidene]-1-methyltetrahydro-4(1H)-pyridinone；3-(4-Methoxy-benzylidene)-1-methyl-piperidin-4-one；(3E)-3-[(4-methoxyphenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 1131012-50-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: UXZFMRNXQJXNAC-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxybenzylidene)-1-methylpiperidin-4-one 、 Alpha,4-二氯苯甲醛肟 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.16h， 以63%的产率得到3-(4-chlorophenyl)-4-(4-methoxyphenyl)-7-methyl-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one
  参考文献：
  名称：

  A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines

  摘要：

  An efficient synthesis of 1-methyl-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones was achieved by the reaction of 1-methyl-4-piperidone and aromatic aldehydes in the presence of pyrrolidine under solvent-free microwave irradiation. These dipolarophiles upon cycloaddition with nitrile oxide and azomethine ylides afford stereoselectively novel spiro-isoxazolines, pyrrolizines and pyrrolidines respectively in excellent yields. The spiro compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) using agar dilution method. Among the synthesized compounds, 1-methyl-4-(2,4-dichlorophenyl)pyrrolo(spiro[2.3 '']oxindole)spiro[3.3']-1'-methylpiperidin-4'-one was found to be the most active with a minimum inhibitory concentration (MIC) of 1.76 and 0.88 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.010
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 4-甲氧基苯甲醛 在 四氢吡咯 作用下， 反应 0.03h， 生成 (E)-3-(4-methoxybenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  超声条件下绿色合成环己酮类似物的不对称双亚芳基衍生物

  摘要：

  摘要开发了一种用于合成两个环己酮类似物的不对称双亚芳基衍生物的新方法。在温和的超声/有机催化条件下，第一醛与酮反应生成单亚芳基中间体，随后在向反应混合物中添加NaOH / MeOH时，其与第二醛缩合。两种冷凝都在一个锅中进行，并且在相对短的时间段内获得了高产率的相应产物。结果表明，该方法也可用于合成单亚芳基对应物。 图形概要

  DOI：

  10.1007/s13738-018-1498-5

文献信息

• Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes
  作者：Xin Gu、Xiaoyan Wang、Fengtian Wang、Hongbao Sun、Jie Liu、Yongmei Xie、Mingli Xiang

  DOI：10.3390/molecules19021976

  日期：——

  An efficient method for the facile synthesis of (E)-monoarylidene derivatives of homo- and heterocyclic ketones with various aldehydes in the presence of a pyrrolidine organocatalyst has been achieved. A range of α,β-unsaturated ketones were obtained in moderate to high yields (up to 99%). Unlike the Claisen-Schmidt condensation process, the formation of undesired bisarylidene byproducts is not observed. The possible reaction mechanism suggests that the reaction proceeds via a Mannich-elimination sequence.

  在吡咯烷有机催化剂的作用下，实现了一种高效的方法，可以方便地合成同环酮和杂环酮与各种醛的 (E)- 单芳基衍生物。一系列 α、β-不饱和酮以中等至高产率（高达 99%）获得。与 Claisen-Schmidt 缩合过程不同的是，没有观察到不需要的双亚芳基副产物的形成。可能的反应机理表明，反应是通过曼尼希-消除顺序进行的。
• A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines
  作者：Raju Ranjith Kumar、Subbu Perumal、Palaniappan Senthilkumar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.05.010

  日期：2009.9

  An efficient synthesis of 1-methyl-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones was achieved by the reaction of 1-methyl-4-piperidone and aromatic aldehydes in the presence of pyrrolidine under solvent-free microwave irradiation. These dipolarophiles upon cycloaddition with nitrile oxide and azomethine ylides afford stereoselectively novel spiro-isoxazolines, pyrrolizines and pyrrolidines respectively in excellent yields. The spiro compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) using agar dilution method. Among the synthesized compounds, 1-methyl-4-(2,4-dichlorophenyl)pyrrolo(spiro[2.3 '']oxindole)spiro[3.3']-1'-methylpiperidin-4'-one was found to be the most active with a minimum inhibitory concentration (MIC) of 1.76 and 0.88 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Green synthesis of dissymmetric bisarylidene derivatives of cyclohexanone analogues under ultrasonic conditions
  作者：Mohammad M. Mojtahedi、Leila Afshinpoor、Fatemeh Karimi、M. Saeed Abaee

  DOI：10.1007/s13738-018-1498-5

  日期：2019.2

  AbstractA new procedure is developed for the synthesis of dissymmetric bisarylidene derivatives of two cyclohexanone analogues. Under mild ultrasonic/organocatalytic conditions, the first aldehyde reacts with the ketone to give the monoarylidene intermediate which subsequently condenses with the second aldehyde upon addition of NaOH/MeOH to the reaction mixture. Both condensations proceed in one pot

  摘要开发了一种用于合成两个环己酮类似物的不对称双亚芳基衍生物的新方法。在温和的超声/有机催化条件下，第一醛与酮反应生成单亚芳基中间体，随后在向反应混合物中添加NaOH / MeOH时，其与第二醛缩合。两种冷凝都在一个锅中进行，并且在相对短的时间段内获得了高产率的相应产物。结果表明，该方法也可用于合成单亚芳基对应物。 图形概要