3,5-bis-(4-bromobenzylidene)-1-methylpiperidin-4-one | 52835-62-8

• 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: 3,5-bis-(4-bromobenzylidene)-1-methylpiperidin-4-one
• 英文别名: 3,5-Bis[(4-bromophenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 52835-62-8
• 化学式: C₂₀H₁₇Br₂NO
• 分子量: 447.169
• InChiKey: CSEWJOXSVCTUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis-(4-bromobenzylidene)-1-methylpiperidin-4-one 、 甲基肼 在 MCM-41-embedded α-iron(III) oxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以90%的产率得到
  参考文献：
  名称：

  (α-Fe2O3)-MCM-41 as a magnetically recoverable nanocatalyst for the synthesis of pyrazolo[4,3-c]pyridines at room temperature

  摘要：

  MCM-41 embedded magnetic nanoparticles which was prepared through the formation of MCM-41 in the presence of Fe3O4 nanoparticles has been used as a magnetically recoverable catalyst for the synthesis of new series of pyrazolo[3,4-c]pyridine derivatives. This catalyst with 10 wt.% of loaded iron oxide nanoparticles 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 X-ray powder diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared (FT-IR), nitrogen physisorption measurements, and acid-base titration. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2012.05.022
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 对溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3,5-bis-(4-bromobenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  微波辐射合成吡喃并[3,2- c ]吡啶衍生物的有效方法

  摘要：

  通过以下反应合成了一系列吡喃并[3,2- c ]吡啶衍生物3,5-二亚苄基-哌啶-4-一和丙二腈在N，N-二甲基甲酰胺在微波辐射下。构建吡喃并[3,2- c ]吡啶骨架是一种简单，高效，有前途的合成方法。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.152

文献信息

• High Anti-cancer Activity, Low Animal Toxicity, and Structure Activity Relationships of Curcumin Analogs
  作者：Sen-Chuan Song、Yu-Liang Mai、Hua-Hong Shi、Bing Liao、Fei Wang

  DOI：10.2174/2352096513999200714103641

  日期：2020.10.23

  both in vitro and in vivo, and their structure activity relationships (SARs) were determined. Methods: Based on the parent structure of curcumin, 81 analogs of 3,5-bis(substitutedbenzylidene)- piperidin-4-one compounds were designed and synthesized. Their anti-cancer activity in the human cancer cell lines was evaluated using the MTT assay, and in vivo toxicity was evaluated in mice. The SARs of selected

  背景：抑制癌细胞生长和降低体内毒性是开发抗癌药物的两个重要标准。姜黄素是开发新型抗癌药物类似物的有希望的候选者。该研究小组设计了姜黄素的3,5-双-（3,4,5-三甲氧基亚苄基）-1-甲基-哌啶-4-一类似物，该类似物可显着抑制体内食管癌细胞的生长。在这项研究中，合成了81个姜黄素类似物，在体内外进行了分析，并确定了它们的结构活性关系（SAR）。 方法：根据姜黄素的母体结构，设计合成了3,5-双（取代亚苄基）-哌啶-4-酮化合物的81个类似物。使用MTT分析评估了它们在人类癌细胞系中的抗癌活性，并评估了小鼠体内毒性。分析了所选化合物的SAR。 结果与讨论：在设计的姜黄素类似物中，有61种化合物在体外具有比母体化合物更高的抗癌作用。23种化合物以低浓度（低于1μM的IC50值）抑制人癌细胞系中的细胞生长。在小鼠中测试了姜黄素类似物的急性毒性。选择了13种化合物，它们在高达25.0 mg /
• An Efficient and Chemoselective Synthesis of 1,6-Naphthyridines and Pyrano[3,2-c]pyridines under Microwave Irradiation
  作者：Shu-Jiang Tu、Zheng-Guo Han、Bo Jiang、Shu Yan、Xiao-Hong Zhang、Shan-Shan Wu、Wen-Juan Hao、Xu-Dong Cao、Feng Shi、Ge Zhang、Ning Ma

  DOI：10.1055/s-0028-1088052

  日期：2009.5

  6-naphthyridines and pyrano[3,2-c]pyridines were selectively synthesized via microwave-assisted reactions controlled by the nature of the solvent. This has resulted in an efficient and promising synthetic method for constructing the 1,6-naphthyridine and pyrano[3,2-c]pyridine skeletons. solvent-dependent chemoselectivity - 1,6-naphthyridines - pyrano[3,2-c]pyridines

  通过受溶剂性质控制的微波辅助反应，有选择地合成了一系列的1,6-萘啶和吡喃并[3,2- c ]吡啶。这导致了一种有效且有前途的合成方法，用于构建1,6-萘吡啶和吡喃并[3,2- c ]吡啶骨架。 溶剂依赖性化学选择性-1,6-萘吡啶-吡喃并[3,2- c ]吡啶
• An efficient method for synthesis of pyrano[3,2-<i>c</i>]pyridine derivatives under microwave irradiation
  作者：Shu-Liang Wang、Zheng-Guo Han、Shu-Jiang Tu、Xiao-Hong Zhang、Shu Yan、Wen-Juan Hao、Feng Shi、Xu-Dong Cao、Shan-Shan Wu

  DOI：10.1002/jhet.152

  日期：2009.9

  A series of pyrano[3,2-c]pyridine derivatives were synthesized via reactions of 3,5-dibenzylidene-piperidin-4-one and malononitrile in N,N-dimethylformamide under microwave irradiation. It is a simple, efficient, and promising synthetic method to construct pyrano[3,2-c]pyridine skeleton. J. Heterocyclic Chem., (2009).

  通过以下反应合成了一系列吡喃并[3,2- c ]吡啶衍生物3,5-二亚苄基-哌啶-4-一和丙二腈在N，N-二甲基甲酰胺在微波辐射下。构建吡喃并[3,2- c ]吡啶骨架是一种简单，高效，有前途的合成方法。J.杂环化​​学，（2009）。
• Magnetic Graphene Oxide Anchored Sulfonic Acid as a Novel Nanocatalyst for the Synthesis of N-aryl-2-amino-1,6-naphthyridines
  作者：Shahnaz Rostamizadeh、Mina Rezgi、Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1002/jccs.201300167

  日期：2013.11

  Magnetic graphene oxide functionalized with sulfonic acid (Fe3O4‐GO‐SO3H) was used as a new recyclable nanocatalyst for one‐pot synthesis of N‐aryl‐2‐amino‐1,6‐naphthyridine derivatives under solvent free conditions. The catalyst could be easily recovered from the reaction mixture by an external magnet and reused without significant decrease in activity even after 4 runs. This nanocatalyst exhibited

  磺酸功能化的磁性氧化石墨烯（Fe 3 O 4 -GO-SO 3 H）被用作一种新的可回收纳米催化剂，用于在无溶剂条件下一锅法合成N-芳基-2-氨基-1,6-萘啶衍生物。可以容易地通过外部磁体从反应混合物中回收催化剂，并且即使在4次运行后，活性也不会显着降低地重复使用。该纳米催化剂显示出比其他市售磺酸催化剂更好的活性。
• Quinine-catalyzed enantioselective tandem conjugate addition/intramolecular cyclization of malononitrile and 1,4-dien-3-ones
  作者：Zhi-Peng Hu、Jian Li、Xiao-Gang Yin、Xue-Jing Zhang、Ming Yan

  DOI：10.3998/ark.5550190.0014.301

  日期：——

  An organocatalytic tandem conjugate addition / intramolecular cyclization of malononitrile and conformationally restricted 1,4-dien-3-ones has been developed. A series of cinchona alkaloids and their derivatives were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The reaction gave 2-amino-4H-pyrans with high yield and excellent enantiopurity

  已开发出丙二腈和构象受限的 1,4-二烯-3-酮的有机催化串联共轭加成/分子内环化。研究了一系列金鸡纳生物碱及其衍生物作为催化剂。在没有任何添加剂的情况下，奎宁被发现是最有效的催化剂。该反应仅使用 5 mol% 奎宁作为催化剂，以高收率和优异的对映纯度得到 2-氨基-4H-吡喃。