(3E,5E)-3,5-Bis({[4-(benzyloxy)phenyl]methylidene})-1-methylpiperidin-4-one | 1392316-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E,5E)-3,5-Bis({[4-(benzyloxy)phenyl]methylidene})-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-1-methyl-3,5-bis[(4-phenylmethoxyphenyl)methylidene]piperidin-4-one
• CAS: 1392316-56-1
• 化学式: C₃₄H₃₁NO₃
• 分子量: 501.625
• InChiKey: GZZAGYNRXIWPNT-OQIGUVFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.8
• 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({[4-(benzyloxy)phenyl]methylidene})-1-methylpiperidin-4-one 、 丙二腈 在 mesoporous MCM-41-SO₃H 作用下， 反应 0.67h， 以95%的产率得到(8E)-2-amino-8-[4-(benzyloxy)benzylidene]-4-[4-(benzyloxy)phenyl]-5,6,7,8-tetrahydro-6-methyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile
  参考文献：
  名称：

  MCM-41-SO3H作为高级纳米催化剂在无溶剂合成吡喃并[3,2-c]吡啶衍生物中的应用

  摘要：

  MCM-41-SO 3 H，一种有序的介孔二氧化硅材料，其中具有共价锚定磺酸基团的MCM-41被用作酸性催化剂，可在以下条件下快速并“绿色”合成吡喃并[3,2-c]吡啶衍生物无溶剂条件。与文献报道的常规方法相比，该新颖的合成方法的优点是催化剂的可重复使用性，高产率，短反应时间，简单和易于后处理。

  DOI：

  10.1002/jccs.201100667
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 4-苄氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (3E,5E)-3,5-Bis({[4-(benzyloxy)phenyl]methylidene})-1-methylpiperidin-4-one
  参考文献：
  名称：

  MCM-41-SO3H作为高级纳米催化剂在无溶剂合成吡喃并[3,2-c]吡啶衍生物中的应用

  摘要：

  MCM-41-SO 3 H，一种有序的介孔二氧化硅材料，其中具有共价锚定磺酸基团的MCM-41被用作酸性催化剂，可在以下条件下快速并“绿色”合成吡喃并[3,2-c]吡啶衍生物无溶剂条件。与文献报道的常规方法相比，该新颖的合成方法的优点是催化剂的可重复使用性，高产率，短反应时间，简单和易于后处理。

  DOI：

  10.1002/jccs.201100667

文献信息

• Application of MCM-41-SO3H as an Advanced Nanocatalyst for the Solvent Free Synthesis of Pyrano[3,2-c]pyridine Derivatives
  作者：Shahnaz Rostamizadeh、Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1002/jccs.201100667

  日期：2012.7

  MCM‐41‐SO3H, an ordered mesoporous silica material in which MCM‐41 with covalently anchored sulfonic acid groups was used as an acidic catalyst for the rapid and ‘green’ synthesis of pyrano[3,2‐c]pyridine derivatives under solvent‐free conditions. Reusability of the catalyst, high yields, short reaction times, simplicity and easy workup are advantages of this novel synthetic procedure compared to the

  MCM-41-SO 3 H，一种有序的介孔二氧化硅材料，其中具有共价锚定磺酸基团的MCM-41被用作酸性催化剂，可在以下条件下快速并“绿色”合成吡喃并[3,2-c]吡啶衍生物无溶剂条件。与文献报道的常规方法相比，该新颖的合成方法的优点是催化剂的可重复使用性，高产率，短反应时间，简单和易于后处理。
• Efficient synthesis of pyrano[3,2-c]pyridines via a green and catalyst-free method at ambient temperature, and related DFT calculations
  作者：Shahnaz Rostamizadeh、M. Z. Kassaee、Nasrin Shadjou、Hassan Zandi

  DOI：10.1007/s00706-012-0851-0

  日期：2013.5

  Twelve medicinally important pyrano[3,2-c]pyridine derivatives were precipitated, with high yields, from ethanol solutions of malononitrile and (E)-3,5-bis(benzylidene)-4-piperidones at ambient temperature, requiring almost no work-up. Natural bond order calculations at the B3LYP/6-31+G* level indicate that electron-withdrawing groups on the phenyl rings deplete electron density on beta-atoms (with respect to the carbonyl groups) of the piperidones, leading to higher yields of the corresponding products with shorter reaction times. This green methodology appears in a clear contrast to all previous reports, where either a catalyst and/or microwave was employed. So, simplicity and short reaction time, non-toxicity of the solvent, as well as economic feasibility are major advantages of this chemically waste-free process.
• Amino functionalized mesoporous silica decorated with iron oxide nanoparticles as a magnetically recoverable nanoreactor for the synthesis of a new series of 2,4-diphenylpyrido[4,3-d]pyrimidines
  作者：Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1039/c4ra00038b

  日期：——

  (Fe2O3)–MCM-41–nPrNH2 as a magnetically recoverable nanoreactor, was prepared through the reaction of (Fe2O3)–MCM-41 with 3-aminopropyltriethoxysilane in refluxing dry toluene. The catalyst with 10 wt% of loaded iron oxide nanoparticles was found to be a highly efficient nanocatalyst for the synthesis of a new class of 2,4-diphenylpyrido[4,3-d]pyrimidines under solvent free conditions in high to quantitative yields. By using an external magnet the catalyst was recovered and reused several times without any loss of efficiency. The prepared catalyst was characterized by transmission electron microscopy (TEM), Fourier transform infrared (FT-IR) spectroscopy, X-ray powder diffraction (XRD), and nitrogen physisorption measurements.

  (Fe2O3)–MCM-41–nPrNH2作为一种可磁性回收的纳米反应器，通过在干燥甲苯中回流(Fe2O3)–MCM-41与3-氨丙基三乙氧基硅烷的反应制备而成。含有10 wt%负载的氧化铁纳米颗粒的催化剂被发现是一种高效的纳米催化剂，在无溶剂条件下合成新型2,4-二苯基吡啶并[4,3-d]嘧啶，产率高到接近定量。通过使用外部磁铁，催化剂可以被回收并多次重复使用，而没有效率损失。制备的催化剂通过透射电子显微镜(TEM)、傅里叶变换红外光谱(FT-IR)、X射线粉末衍射(XRD)和氮气物理吸附测量进行了表征。