1-(4-甲氧基苯磺酰基)哌啶 | 35088-89-2

• 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: 1-(4-甲氧基苯磺酰基)哌啶
• 英文名称: 1-((4-methoxyphenyl)sulfonyl)piperidine
• 英文别名: 1-(4-methoxybenzenesulfonyl)-piperidine；1-[(4-methoxyphenyl)sulfonyl]piperidine；1-(4-methoxy-benzenesulfonyl)-piperidine；1-(4-Methoxy-benzolsulfonyl)-piperidin；4-Methoxy-benzolsulfonsaeure-piperidid；1-((p-Methoxyphenyl)sulfonyl)piperidine；1-(4-methoxyphenyl)sulfonylpiperidine
• CAS: 35088-89-2
• 化学式: C₁₂H₁₇NO₃S
• mdl: MFCD00625655
• 分子量: 255.338
• InChiKey: ZLBJQKXSLZFZSC-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  392.2±44.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苯磺酰基)哌啶 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到4-(piperidin-1-ylsulfonyl)phenol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents

  摘要：

  Novel polar functionalities containing 6-nitro-2,3-dihydroimidazooxazole (NHIO) analogues were synthesized to produce a compound with enhanced solubility. Polar functionalities including sulfonyl, uridyl, and thiouridyl-bearing NHIO analogues were synthesized and evaluated against Mycobacterium tuberculosis (MTB) H(37)Rv. The aqueous solubility of compounds with MIC values <= 0.5 mu g/mL were tested, and six compounds showed enhanced aqueous solubility. The best six compounds were further tested against resistant (Rif(R) and MDR) and dormant strains of MTB and tested for cytotoxicity in HepG2 cell line. Based on its overall in vitro characteristics and solubility profile, compound 6d was further shown to possess high microsomal stability, solubility under all tested biological conditions (PBS, SGF and SIF), and favorable oral in vivo pharmacokinetics and in vivo efficacy.

  DOI：

  10.1021/acsmedchemlett.5b00202
• 作为产物：
  描述：

  sodium 4-methoxybenzenesulfinate 在 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 1-(4-甲氧基苯磺酰基)哌啶
  参考文献：
  名称：

  高价碘介导的磺酰胺合成

  摘要：

  描述了由高价碘试剂介导的磺酰基向胺和苯胺的清洁和温和转移。通过该反应，即使以克为单位，也以高达99％的产率合成了总共25种磺酰胺。通过ESI-MS和DFT计算研究了反应机理。

  DOI：

  10.1002/ejoc.201900259

文献信息

• Iodine-catalyzed sulfonylation of sulfonyl hydrazides with <i>tert</i>-amines: a green and efficient protocol for the synthesis of sulfonamides
  作者：Jinyang Chen、Xiaoran Han、Lan Mei、Jinchuan Liu、Kui Du、Tuanwu Cao、Qiang Li

  DOI：10.1039/c9ra07361b

  日期：——

  This study provides a direct, sustainable and eco-friendly method for the synthesis of various sulfonamides via the sulfonylation of sulfonyl hydrazides with tert-amines. The method utilizes sulfonyl hydrazides to oxidize and couple with tertiary amines through selective cleavage of C–N bonds. In this reaction, molecular iodine was used as the catalyst and t-butyl hydroperoxide was used as the oxidant

  该研究为通过磺酰肼与叔胺磺酰化合成各种磺胺类药物提供了一种直接、可持续和环保的方法。该方法利用磺酰肼氧化并通过选择性裂解 C-N 键与叔胺偶联。在该反应中，分子碘用作催化​​剂，叔丁基过氧化氢用作氧化剂。
• Synthesis of sulfonamides via copper-catalyzed oxidative C–N bond cleavage of tertiary amines
  作者：Jing Ji、Zhengyi Liu、Ping Liu、Peipei Sun

  DOI：10.1039/c6ob01208f

  日期：——

  A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C–N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.

  开发了铜催化的磺酰氯与叔胺通过叔胺的氧化C–N键裂解的偶联反应。使用该策略以中等至良好的产率合成了磺酰胺。该反应适用于各种叔胺以及磺酰氯。
• TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with <i>tert</i>-amines
  作者：Hongmei Jiang、Xiaoyue Tang、Zhihui Xu、Huixian Wang、Kang Han、Xiaolan Yang、Yuanyuan Zhou、Yong-Lai Feng、Xian-Yong Yu、Qingwen Gui

  DOI：10.1039/c8ob02992j

  日期：——

  A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C–N and C–H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity

  一种简单，实用和不含金属的方法已被开发用于磺酰胺和β-芳基磺酰基的烯胺的合成通过的C-N和C-H键的选择性裂解通过芳烃磺酰基氯化物和钠基亚磺酸盐的碘催化氧化用叔-胺类。该方法使用可商购的廉价催化剂和氧化剂，并且具有广泛的底物范围和操作简便性。
• Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides
  作者：Andrei Shavnya、Steven B. Coffey、Aaron C. Smith、Vincent Mascitti

  DOI：10.1021/ol403072r

  日期：2013.12.20

  A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The

  描述了新颖的钯催化的芳基和杂芳基卤化物的硫化。该反应在温和的条件下进行，并提供了广泛的芳基和杂芳基亚磺酸盐，这是一种有用且用途广泛的合成中间体。利用这种硫化反应，还开发了一种一锅法，可以直接使用砜和磺酰胺。这些转化的实用性通过药物万艾可类似物的平行合成得到了说明。
• Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
  作者：Weixi Zhang、Meiming Luo

  DOI：10.1039/c5cc09830k

  日期：——

  A novel strategy for installation of sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine...

  通过铁催化的自由基偶联反应已经实现了将磺酰基片段安装到芳烃中的新策略。通过单电子转移反应衍生自二芳基鎓的芳烃自由基结合...