(3E,5E)-1-methyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one

• 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: (3E,5E)-1-methyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one
• 英文别名: (E)-1-methyl-3,5-bis(4-nitrobenzylidene)-4-piperidone；3.5-bis(4-nitrobenzylidene)-1-methyl-4-piperidone；1-methyl-3,5-bis-(4-nitro-benzylidene)-piperidin-4-one；1-Methyl-3,5-bis-(4-nitro-benzyliden)-piperidin-4-on；(3E,5E)-1-methyl-3,5-bis[(4-nitrophenyl)methylidene]piperidin-4-one
• 化学式: C₂₀H₁₇N₃O₅
• 分子量: 379.372
• InChiKey: RZSZIUWKHOTPLG-OTYYAQKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3E,5E)-1-methyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one 在 四氯苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 (E)-7-methyl-2-(methylthio)-9-(4-nitrobenzylidene)-5-(4-nitrophenyl)-6,7,8,9-tetrahydropyrimido[4,5-b][1,6]naphthyridin-4(3H)-one
  参考文献：
  名称：

  微波辅助合成具有潜在抗肿瘤活性的嘧啶并[4,5- b ] [1,6]萘啶-4（3 H）-酮

  摘要：

  的6,7,8,9-四氢嘧啶并[4,5- b ] [1,6]萘啶-4（3 H ^，5 ħ，10 ħ） -酮4，图5a -克和它们的氧化形式6，图7a -克从6-氨基-2-甲硫基-4（3无催化剂反应获得ħ） -酮3和（ë）-3,5-双（亚苄基）-1-烷基-4-哌啶酮1，图2a – g在微波辐射下及其随后的氧化过程中，p-氯苯胺。在美国国家癌症研究所（NCI）中评估了18种新化合物，其中化合物4g对57种癌细胞具有显着活性，体外试验中最重要的GI 50值范围为1.48至9.92μM。

  DOI：

  10.1016/j.ejmech.2012.11.037
• 作为产物：
  描述：

  1-甲基-4-哌啶酮-3-羧酸甲酯 在 盐酸 、 水 、 溶剂黄146 作用下， 生成 (3E,5E)-1-methyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one
  参考文献：
  名称：

  1,3-DIMETHYLPIPERIDONE-4

  摘要：

  DOI：

  10.1021/jo01180a003

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。
• 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。
• Catalytic Activity of (Fe<SUB>2</SUB>O<SUB>3</SUB>)-MCM-41-nPrNH<SUB>2</SUB> Magnetically Recoverable Nanocatalyst for the Synthesis of Phenylpyrido[4,3-d]Pyrimidins
  作者：Shahnaz Rostamizadeh、Nasrin Shadjou、Elyass Isapoor、Mohammad Hasanzadeh

  DOI：10.1166/jnn.2013.7582

  日期：2013.7.1

  A new series of phenylpyrido[4,3-d]pyrimidin-2-amin derivatives have been synthesised from the reaction of (E)-3,5-bis(benzylidene)-4-piperidones and guanidine carbonate in the presence of (Fe2O3)-MCM-41-nPrNH2 as a magnetically recoverable nanocatalyst under solvent free conditions. This catalyst was highly recyclable (up to 5 times) and was easily recovered from the reaction mixture using an external magnet without loss of activity. The prepared magnetic catalyst is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), and nitrogen physisorption measurements. Also all the structures of title compounds 3a–h were elucidated by comprehensive 1H NMR,13C NMR, IR and Mass spectra.

  在无溶剂条件下，以 (Fe2O3)-MCM-41-nPrNH2 为磁性可回收纳米催化剂，通过 (E)-3,5-双(亚苄基)-4-哌啶酮和碳酸胍的反应合成了一系列新的苯基吡啶并[4,3-d]嘧啶-2-氨基衍生物。这种催化剂具有很强的可回收性（最多可回收 5 次），使用外部磁铁就能轻松地从反应混合物中回收，且不会丧失活性。所制备的磁性催化剂通过傅立叶变换红外（FT-IR）、X 射线粉末衍射（XRD）和氮气物理吸附测量进行了表征。此外，标题化合物 3a-h 的结构也通过 1H、13C NMR、IR 和质谱得到了全面的阐明。
• A Facile Stereoselective Domino Approach for the Construction of Novel Bis(spiropiperidone)–Tetrahydrothiophene Hybrid Heterocycles
  作者：Subbu Perumal、Chelliah Bharkavi、Sundaravel Kumar

  DOI：10.1055/s-0034-1380722

  日期：——

  A library of novel bis-spiropiperidone–tetrahydrothiophene hybrid heterocycles have been synthesized via pseudo-three-component domino reaction of (3 E ,5 E )-3,5-bis(arylidene)-1-methyl/benzyl piperidin-4-ones and 1,4-dithiane-2,5-diol in the presence of triethylamine. This transformation presumably proceeds via two annulations each involving the generation of 2-mercaptoacetaldehyde from 1,4-dithiane-2

  通过 (3 E ,5 E )-3,5-双(亚芳基)-1-甲基/苄基哌啶-4-酮的假三组分多米诺反应合成了新型双螺哌啶酮-四氢噻吩杂环化合物库和 1,4-二噻烷-2,5-二醇在三乙胺的存在下。这种转化大概是通过两个环化进行的，每个环化都涉及从 1,4-二噻烷-2,5-二醇-迈克尔加成-分子内醛醇序列生成 2-巯基乙醛，这导致在一锅操作中产生四个新键。该协议的优点是原子经济性高、立体选择性高、反应时间短、操作简单。
• Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents
  作者：Hussein I. El-Subbagh、Suhair M. Abu-Zaid、Mona A. Mahran、Farid A. Badria、Abdulrahman M. Al-Obaid

  DOI：10.1021/jm000038m

  日期：2000.7.1

  A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3,2-c]pyridines, as flavone and coumarin isosteres, were synthesized and screened for their in vitro antiviral and antitumor activities at the National Cancer Institute (NCI). Compounds 9 and 18 proved to be active against herpes simplex virus-1 (HSV-1), while compound 13 showed moderate activity against human immunodeficiency virus-1 (HIV-1). Compounds 14, 26, 28, 33, and 35 exhibited a broad spectrum antitumor activity. In addition, compounds 26, 33, and 35 proved to be of moderate selectivity toward leukemia cell lines. The pyrano[3,2-c]pyridines heterocyclic system proved to be the most active antitumors among the investigated heterocycles.