1-benzyl-4-tosylpiperazine | 95558-32-0

• 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: 1-benzyl-4-tosylpiperazine
• 英文别名: 1-Benzyl-4-[(4-methylphenyl)sulfonyl]piperazine；1-benzyl-4-(4-methylphenyl)sulfonylpiperazine
• CAS: 95558-32-0
• 化学式: C₁₈H₂₂N₂O₂S
• mdl: MFCD00832325
• 分子量: 330.451
• InChiKey: AVLMRGRKHPZMGH-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  467.5±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-tosylpiperazine 在 potassium fluoride on basic alumina 作用下， 反应 0.1h， 以80%的产率得到1-苄基哌嗪
  参考文献：
  名称：

  Microwave Assisted Selective Cleavage of Sulfonates and Sulfonamides in Dry Media

  摘要：

  首次在微波辐射条件下，采用KF-Al2O3成功实现了磺酸盐和磺酰胺的简单高效裂解方法。

  DOI：

  10.1055/s-1999-2940
• 作为产物：
  描述：

  toluene sulfonyl chloride 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 1-benzyl-4-tosylpiperazine
  参考文献：
  名称：

  One-Step Cyclization: Synthesis of N-Heteroalkyl-N′-tosylpiperazines

  摘要：

  Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (S-N) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.

  DOI：

  10.1021/jo3012896

文献信息

• PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
  作者：Debayan Sarkar、Manoj Kumar Ghosh、Nilendri Rout

  DOI：10.1016/j.tetlet.2018.05.017

  日期：2018.6

  A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral

  已经描述了一种简便的方法，该方法已成功简化了磺酰胺，硫代磺酸盐和对称二硫烷的生成。这种“三重”反应发生在无金属的露天气氛中，并且也已按比例放大至克，使其适合商业化。该反应还已经成功地用不对称变体进行，因此有助于手性库。用户友好的“三重奏”能够轻松生成这些多用途的硫类似物，并且所采用的反应条件反映了经济状况。
• Base-free monosulfonylation of amines using tosyl or mesyl chloride in water
  作者：Ahmed Kamal、J. Surendranadha Reddy、E. Vijaya Bharathi、D. Dastagiri

  DOI：10.1016/j.tetlet.2007.11.044

  日期：2008.1

  A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.

  在室温下使用甲磺酰或甲苯磺酰氯在水中开发了一种温和有效的程序，用于各种胺的单磺酰化反应，从而以高收率得到相应的磺酰胺。
• Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives
  作者：Maloy Kumar Parai、Gautam Panda、Kumkum Srivastava、Sunil Kumar Puri

  DOI：10.1016/j.bmcl.2007.11.038

  日期：2008.1

  A new series of benzene and isoquinoline sulfonamide derivatives were synthesized by nucleophilic displacement reaction on benzene and isoquinoline sulfonyl chlorides by substituted amines (primary and secondary). The title compounds were evaluated for antimalarial activity against Plasmodium falciparum in vitro and showed MIC in the range of 2-50 microg/mL.

  通过取代胺（伯胺和仲胺）在苯和异喹啉磺酰氯上的亲核取代反应，合成了一系列新的苯和异喹啉磺酰胺衍生物。评价了标题化合物在体外对恶性疟原虫的抗疟活性，并且其MIC在2-50μg/ mL的范围内。
• Nitrolysis of urethanes derived from secondary alcohols as a new method for the synthesis of secondaryN-nitroamines
  作者：O. A. Luk'yanov、T. G. Mel'nikova、M. E. Shagaeva

  DOI：10.1007/bf02503484

  日期：1998.6

  The reactions of dialkylurethanes R12NCOOR (RO is the residue of a secondary but not a primary alcohol) with nitrating reagents leads to the formation of the corresponding sccondaryN-nitroamines R12NNO2.

  二烷基氨基甲酸乙酯 R12NCOOR（RO 是仲醇而非伯醇的残基）与硝化试剂的反应导致形成相应的仲 N-硝基胺 R12NNO2。
• Design, synthesis, pharmacological and in silico screening of disubstituted-piperazine derivatives as selective and reversible MAO-A inhibitors for treatment of depression
  作者：Nilay Kumar Nandi、Rohit Bhatia、Suresh Saini、Ravi Rawat、Shilpa Sharma、Khadga Raj、Naresh Rangra、Bhupinder Kumar

  DOI：10.1016/j.molstruc.2022.134671

  日期：2023.3

  Monoamine oxidase-A inhibitors (MAO-AIs) are potential drug candidates for the treatment of depression. In the present study, a series of substituted benzenesulfonyl piperazine (NP1-NP16) derivatives was synthesized and screened for their MAO-A and MAO-B inhibitory activity using the Amplex Red assay. Most of the synthesized compounds were found to show selective inhibition of MAO-A isoform. Compounds

  单胺氧化酶-A 抑制剂 (MAO-AIs) 是治疗抑郁症的潜在候选药物。在本研究中，合成了一系列取代的苯磺酰基哌嗪 ( NP1-NP16 ) 衍生物，并使用 Amplex Red 测定法筛选了它们的 MAO-A 和 MAO-B 抑制活性。发现大多数合成化合物显示出对 MAO-A 亚型的选择性抑制作用。化合物NP4和化合物NP12显示出最有效的 MAO-A 抑制剂活性，IC 50值分别为 0.25 ± 0.04 μM 和 0.46 ± 0.02 μM，并且这两种化合物都是可逆抑制剂。复合NP4被发现作为 MAO-A 抑制剂最具选择性，选择性是 MAO-B 同种型的 52 倍。在细胞毒性评估中，发现这些化合物对 SH-SY5Y 细胞无毒，并且还表现出神经保护特性。在 DPPH 研究中，化合物NP4和NP12在浓度为 1 mM 时通过将吸光度降低约 50% 显示出自由基清除活性。在体内强迫游泳试验