(E)-1-methyl-3,5-bis(4-methoxybenzylidene)-4-piperidone | 4369-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-methyl-3,5-bis(4-methoxybenzylidene)-4-piperidone
• 英文别名: 3,5-bis((E)-4-methoxybenzylidene)-1-methylpiperidin-4-one；3,5-Bis(4-methoxybenzylidene)-1-methyl-4-piperidinone；(3E,5E)-3,5-bis[(4-methoxyphenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 4369-12-4
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: OKMDTMGJNJKWAE-KLCVKJMQSA-N

物化性质

• 熔点：
  202-204 °C(Solv: ethanol (64-17-5))
• 沸点：
  552.9±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-3,5-bis(4-methoxybenzylidene)-4-piperidone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(3E,5E)-3,5-bis[(4-methoxyphenyl)methylidene]-1-methylpiperidin-4-ol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents

  摘要：

  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.

  DOI：

  10.1021/jm000038m
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 (E)-1-methyl-3,5-bis(4-methoxybenzylidene)-4-piperidone
  参考文献：
  名称：

  一种高度原子经济，化学，区域和立体选择性的合成方法以及螺吡咯并噻唑类抗结核药的评估

  摘要：

  源自取代的靛红和1,3-噻唑烷-4-羧酸的偶氮甲亚胺的1,3-偶极环加成反应生成一系列1-甲基-3,5-双[（E）-芳基亚甲基]-四氢-4（ 1 H）-吡啶酮以定量产率提供了化学，区域和立体选择性的新型螺-吡咯并噻唑。使用琼脂稀释法筛选这些化合物的抗结核分枝杆菌H37Rv（MTB）和耐多药结核分枝杆菌（MDR-TB）的体外活性。在合成的化合物中，螺[5.3''-5''-硝基氧吲哚-螺-[6.3']-1'-甲基-5'-（2,4-二氯苯基亚甲基）四氢-4'（1 H）吡啶酮-7-（2,4-二氯苯基）四氢-1 H-吡咯并[1,2-发现c ] [1,3]噻唑（9k）最具活性，对MTB和MDR-TB的最低抑菌浓度（MIC）为0.6μM。

  DOI：

  10.1016/j.bmcl.2009.10.107

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。
• Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents
  作者：Khairia M. Youssef、Magda A. El-Sherbeny、Faiza S. El-Shafie、Hassan A. Farag、Omar A. Al-Deeb、Sit Albanat A. Awadalla

  DOI：10.1002/ardp.200300763

  日期：2004.1

  New series of 3, 5‐bis(substituted benzylidene)‐4‐piperidones, 2, 7‐bis(substituted benzylidene)cycloheptanones, 1, 5‐bis(substituted phenyl)‐1, 4‐pentadien‐3‐ones, 1, 7‐bis(substituted phenyl)‐1, 6‐heptadien‐3, 5‐diones, 1, 1‐bis(substituted cinnamoyl)‐cyclopentanes, and 1, 1‐bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds

  新系列 3, 5-双（取代苯亚甲基）-4-哌啶酮，2, 7-双（取代苯亚甲基）环庚酮，1, 5-双（取代苯基）-1，4-戊二烯-3-，1， 7-双（取代苯基）-1, 6-庚二烯-3, 5-二酮，1, 1-双（取代肉桂酰基）-环戊烷和1, 1-双（取代肉桂酰基）环己烷已合成并测试其性能抗氧化活性。在被测化合物中，化合物II4、II9、II10、II11、V1和V4表现出较高的自由基清除活性，%抑制率分别为90.71、91.24、96.91、94.26、99.23和99.85%。此外，化合物 V1 是外周多核中性粒细胞 (PMN) 的安全成员，存活率为 91%。报告了详细的合成、光谱和生物学数据。
• Synthesis and spectroscopic and structural studies of cross-conjugated dienones derived from cyclic ketones and aromatic aldehydes
  作者：S. Z. Vatsadze、M. A. Manaenkova、N. V. Sviridenkova、N. V. Zyk、D. P. Krut’ko、A. V. Churakov、M. Yu. Antipin、J. A. K. Howard、H. Lang

  DOI：10.1007/s11172-006-0397-6

  日期：2006.7

  Cross-conjugated dienones were synthesized by the reactions of cyclic ketones with two equivalents of aromatic aldehydes under basic conditions. An NMR spectroscopic study and X-ray diffraction analysis demonstrated that all reaction products are formed as E,E isomers. Spontaneous photochemical trans-cis isomerization of cross-conjugated dienones under the scattered light in solution was observed for

  交叉共轭二烯酮是通过环状酮与两当量的芳香醛在碱性条件下反应合成的。NMR 光谱研究和 X 射线衍射分析表明，所有反应产物均以 E、E 异构体的形式形成。首次观察到溶液中散射光下交叉共轭二烯酮的自发光化学反顺异构化。异构化程度主要取决于二烯酮分子中心片段的性质。合成了以前未知的 2,5-双 [(E)-(3-吡啶基) 亚甲基] 环戊酮的光化学 [2+2]-环加成产物，并通过光谱方法和 X 射线衍射进行了表征。在所使用的条件下，仅获得环丁烷加合物的一种异构体。
• 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。
• Microwave-assisted synthesis of pyrimido[4,5-b][1,6]naphthyridin-4(3H)-ones with potential antitumor activity
  作者：Braulio Insuasty、Diana Becerra、Jairo Quiroga、Rodrigo Abonia、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.ejmech.2012.11.037

  日期：2013.2

  The 6,7,8,9-tetrahydropyrimido[4,5-b][1,6]naphthyridin-4(3H,5H,10H)-ones 4,5a–g and their oxidized forms 6,7a–g were obtained from the catalyst-free reaction of 6-amino-2-methylthiopyrimidin-4(3H)-one 3 and (E)-3,5-bis(benzylidene)-1-alkyl-4-piperidones 1,2a–g under Microwave irradiation and their subsequent oxidation process with p-chloranil. Eighteen of the new compounds were evaluated in the US

  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。