2-甲基-1-(4-硝基苯基磺酰基)哌啶 | 346689-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-1-(4-硝基苯基磺酰基)哌啶
• 英文名称: 2-methyl-1-(4-nitrophenylsulfonyl)piperidine
• 英文别名: 2-Methyl-1-(4-nitrophenyl)sulfonylpiperidine
• CAS: 346689-79-0
• 化学式: C₁₂H₁₆N₂O₄S
• 分子量: 284.336
• InChiKey: IBATUZBCIWHCAC-UHFFFAOYSA-N

物化性质

• 沸点：
  437.0±47.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)
• 溶解度：
  22.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基-1-(4-硝基苯基磺酰基)哌啶 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0~120.0 ℃ 、506.66 kPa 条件下， 反应 8.0h， 生成 2-(4-((2-methylpiperidin-1-yl)sulfonyl)phenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3

  摘要：

  High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (<100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.047
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 2-甲基哌啶 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-甲基-1-(4-硝基苯基磺酰基)哌啶
  参考文献：
  名称：

  Potent Non-Nucleoside Inhibitors of the Measles Virus RNA-Dependent RNA Polymerase Complex

  摘要：

  Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds Could conceivably diminish these statistics and provide a therapy that complements vaccine treatment. We recently described a high-throughput screening hit compound 1 (16677) against MV-infected cells with the capacity to eliminate viral reproduction at 250 nM by inhibiting the action of the virus's RNA-dependent RNA polymerase complex (RdRp). The compound, 1-methyl-3-(trifluoroi-nethyl)-N-[4-sulfonylphenyl]-1H-pyrazole-5-carboxamide, 1 carries a critical CF3 moiety on the 1,2-pyrazole ring. Elaborating on the preliminary structure-activity (SAR) study, the present work presents the synthesis and SAR of a much broader range of low nanomolar nonpeptidic MV inhibitors and speculates on the role of the CF3 functionality.

  DOI：

  10.1021/jm701239a

文献信息

• Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
  作者：Joshua J. Clarke、Yuuki Maekawa、Masakazu Nambo、Cathleen M. Crudden

  DOI：10.1021/acs.orglett.1c01892

  日期：2021.9.3

  Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation

  在氢硅烷和氢气氛的存在下，介离子卡宾稳定的硼离子有效地将取代的吡啶还原为哌啶。对照实验和氘标记研究证明了吡啶的可逆氢化硅烷化，能够在较温和的条件下完全还原 N-杂环。硅烷是防止哌啶产物和硼催化剂之间形成加合物的关键反应组分。
• Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds
  作者：Narasimhulu Gandhamsetty、Sehoon Park、Sukbok Chang

  DOI：10.1021/jacs.5b09209

  日期：2015.12.9

  Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp(3) C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence

  已开发出三（五氟苯基）硼烷催化的吡啶甲硅烷基化还原，从而形成 sp(3) C-Si 键选择性地β到氮杂环产品的氮原子。根据吡啶取代基的位置和性质，在硼烷催化下以高选择性获得结构多样的氮杂环。机理研究阐明了这种多重还原级联中氢化硅烷化的顺序：1,2- 或 1,4- 氢化硅烷化作为初始步骤，具体取决于取代基位置，然后选择性氢化硅烷化烯胺双键，最终得到 β-硅烷化氮杂环化合物。