1-Methyl-3,5-bis(3-phenyl-2-propenylidene)-4-piperidinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Methyl-3,5-bis(3-phenyl-2-propenylidene)-4-piperidinone
• 英文别名: (3E,5E)-1-methyl-3,5-bis[(E)-3-phenylprop-2-enylidene]piperidin-4-one
• 化学式: C₂₄H₂₃NO
• 分子量: 341.453
• InChiKey: UZMNXCUMVFUXQA-DCVUGOMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-Methyl-3,5-bis(3-phenyl-2-propenylidene)-4-piperidinone 、 盐酸氨基脲 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以72%的产率得到(7E)-(4,5,6,7-tetrahydro-5-methyl-7-(E)-3-phenylallylidene)-3-styryl pyrazolo[4,3-c]pyridine-2-carboxamide
  参考文献：
  名称：

  Aruna, S.; Girija, R.; Saamanthi, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 5, p. 746 - 754

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 反式肉桂醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 1-Methyl-3,5-bis(3-phenyl-2-propenylidene)-4-piperidinone
  参考文献：
  名称：

  Aruna, S.; Girija, R.; Saamanthi, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 5, p. 746 - 754

  摘要：

  DOI：

文献信息

• Organocatalytic Conjugate Addition of Malononitrile to Conformationally Restricted Dienones
  作者：Zhi-Peng Hu、Chun-Liang Lou、Jin-Jia Wang、Chun-Xia Chen、Ming Yan

  DOI：10.1021/jo200112r

  日期：2011.5.20

  Organocatalytic conjugate addition of malononitrile to conformationally restricted dienones has been studied. A series of chiral primary and tertiary amine catalysts were screened. A piperidine-based thiourea-tertiary amine was found to be the efficient catalyst. Chiral pyran derivatives were obtained in excellent yields and enantioselectivities via a cascade conjugate addition–intramolecular cyclization pathway

  已经研究了丙二腈向构象受限的二烯酮的有机催化共轭加成。筛选了一系列手性伯胺和叔胺催化剂。发现基于哌啶的硫脲叔胺是有效的催化剂。通过级联共轭加成-分子内环化途径获得了高收率和对映选择性的手性吡喃衍生物。对于构象柔性二烯酮的相应反应，该反应明显不同。
• An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles
  作者：Raju Ranjith Kumar、Subbu Perumal、Palaniappan Senthilkumar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2007.09.095

  日期：2007.12

  An atom efficient, green protocol for the synthesis of fifteen 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro4H-pyrano[3,2-c] pyridine-3-carbonitriles in quantitative yields from the reaction of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones with malononitrile in presence of solid sodium ethoxide under solvent-free condition is described. The compounds were tested for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant tuberculosis (MDR-TB), and Mycobacterium smegmatis using agar dilution method. 2-Amino-4-[4-(dimethylamino) phenyl]-8-(E)-[4(dimethylamino) phenyl] methylidene-6-methyl-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]-pyridine-3-carbonitrile was found to be the most potent compound (MIC: 0.43 mu M) against MTB and MDR-TB, being 100 times more active than standard, isoniazid against MDRTB. (c) 2007 Elsevier Ltd. All rights reserved.