(3E,5E)-3,5-bis(furan-2-ylmethylene)-1-methylpiperidin-4-one | 96733-82-3

• 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: (3E,5E)-3,5-bis(furan-2-ylmethylene)-1-methylpiperidin-4-one
• 英文别名: 3,5-Bis(furan-2-ylmethylene)-1-methylpiperidin-4-one；(3E,5E)-3,5-bis(furan-2-ylmethylidene)-1-methylpiperidin-4-one
• CAS: 96733-82-3
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: QQHADRRKKGASTC-QHKWOANTSA-N

物化性质

• 沸点：
  436.9±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(furan-2-ylmethylene)-1-methylpiperidin-4-one 在 氢氧化钾 、 sodium 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 5.0h， 生成 4-Furan-2-yl-8-[1-furan-2-yl-meth-(E)-ylidene]-6-methyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine
  参考文献：
  名称：

  Deli; Lorand; Szabo, Pharmazie, 1984, vol. 39, # 10, p. 681 - 682

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 、 N-甲基-4-哌啶酮 在 四氢吡咯 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (3E,5E)-3,5-bis(furan-2-ylmethylene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  一种双取代芳基类化合物及其应用

  摘要：

  本发明涉及一种双取代芳基类化合物及其应用，所述的双取代芳基类化合物结构如式I、II或III所示，通过实验验证发现该类双取代芳基类化合物可以与唑类抗真菌药物共同使用，可提高耐药菌对唑类药物的敏感性，实现逆转耐药，因此本发明为临床耐药真菌的治疗提供了一种新途径。

  公开号：

  CN106800547B

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。
• Sacrificial azomethine ylide cycloaddition controlled chemoselective nitrile oxide cycloaddition to 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: formation of mono-spiro-isoxazolines
  作者：Raju Ranjith Kumar、Subbu Perumal

  DOI：10.1016/j.tet.2007.09.033

  日期：2007.12

  The 1,3-dipolar cycloaddition of an azomethine ylide to 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrrolidines in good yields. Further cycloaddition of these spiro-pyrrolidines with nitrile oxide afforded mono-spiro-isoxazolines in moderate yields (45–56%), presumably via a di-spiro intermediate, which undergoes a spontaneous cycloreversion of the spiro-pyrrolidine

  偶氮甲碱内酯的1，3-偶极环加成反应成1-甲基-3,5-双[（E）-芳亚甲叉基]四氢-4（1 H）-吡啶酮，以良好的收率提供了新型螺吡咯烷。这些螺吡咯烷与一氧化二氮的进一步环加成，以中等收率（45-56％）提供了单螺-异恶唑啉，大概是通过双螺中间体，螺中间体经历了螺-吡咯烷单元的自发环还原。相反，将一氧化氮直接环加成到1-甲基-3,5-双[（E）-芳亚甲叉基]四氢-4（1 H）-吡啶酮中得到单螺-异恶唑啉作为次要产物，而二主要形成-螺-异恶唑啉。
• [EN] INHIBITORS OF THE WNT/BETA-CATENIN PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE WNT/BÊTA-CATÉNINE
  申请人：UNIV CALIFORNIA

  公开号：WO2019152536A1

  公开（公告）日：2019-08-08

  The present disclosure relates to compounds that are capable of modulating the WNT/Beta-Catenin pathway. The disclosure further relates to methods of treating colorectal cancer and other WNT/Beta-Catenin mediated cancers.

  本披露涉及能够调节WNT/Beta-Catenin通路的化合物。此外，该披露还涉及治疗结直肠癌和其他WNT/Beta-Catenin介导的癌症的方法。
• 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.
• Discovery of Antimycobacterial Spiro-piperidin-4-ones: An Atom Economic, Stereoselective Synthesis, and Biological Intervention
  作者：Raju Ranjith Kumar、Subbu Perumal、Palaniappan Senthilkumar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1021/jm800545k

  日期：2008.9.25

  An atom economic and stereoselective synthesis of several spiro-piperidin-4-ones through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin and (alpha-amino acids viz. proline, phenylglycine, and sarcosine to a series of 1-methyl- 3,5-bis [(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones is described. These compounds were evaluated for their in vitro and in vivo activity against Mycobacterium tuberculosis H37Rv (MTB), multidrug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2). Compound 4-(4-fluorophenyl)-5-phenylpyrrolo(spiro[2.3"]oxindole)spiro[3.3']-1'-methyl-5'-(4-fluorophenylmethylideiie)piperidin-4'-one (4e) was found to be the most active in vitro with a MIC value of 0.07 mu M against MTB and was 5.1 and 67.2 times more potent than isoniazid and ciprofloxacin, respectively. In vivo, compound 4e decreased the bacterial load in lung and spleen tissues with 1.30 and 3.73-log 1.0 protections respectively and was considered to be promising in reducing bacterial count in lung and spleen tissues.