N,N-diallyl-(4-nitrobenzene)sulfonylamine | 35735-57-0

• 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: N,N-diallyl-(4-nitrobenzene)sulfonylamine
• 英文别名: N,N-diallyl-4-nitrobenzenesulfonamide；N,N-diallyl-p-nitrobenzenesulfonamide；N,N-Diallyl-p-nitrobenzolsulfonamid；N,N-diallyl 4-nitrobenzenesulfonamide；4-nitro-N,N-bis(prop-2-enyl)benzenesulfonamide
• CAS: 35735-57-0
• 化学式: C₁₂H₁₄N₂O₄S
• mdl: MFCD01212726
• 分子量: 282.32
• InChiKey: VGAWPVVNQSRFSP-UHFFFAOYSA-N

物化性质

• 熔点：
  61.2-61.9 °C
• 沸点：
  419.5±55.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  N,N-diallyl-(4-nitrobenzene)sulfonylamine 在 盐酸 、 tin 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 N-((4-(N,N-diallylsulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 二烯丙基胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到N,N-diallyl-(4-nitrobenzene)sulfonylamine
  参考文献：
  名称：

  机械化学钌催化的烯烃复分解

  摘要：

  我们描述了 Ru 催化的烯烃复分解的机械化学方法的发展，包括交叉复分解和闭环复分解。该方法使用市售催化剂以不使用或仅使用催化量的液体实现多克规模的固体或液体烯烃的高产率、快速、室温复分解。

  DOI：

  10.1021/jacs.5b00151

文献信息

• Direct use of allylic alcohols in the allylation of sulfonylimidates
  作者：Ryosuke Matsubara、Koichiro Masuda、Jyunya Nakano、Shū Kobayashi

  DOI：10.1039/c0cc03067h

  日期：——

  We have developed catalytic allylation reactions of sulfonylimidates using allylic alcohols as allylating reagents. Stoichiometric amounts of neither activators nor bases are required in this reaction.

  我们已开发出使用烯丙醇作为烯丙基化试剂的磺酰亚胺酯的催化烯丙基化反应。该反应不需要任何活化剂或碱的化学计量量。
• Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
  作者：Weiqiang Chen、Yin-Lin Zhang、Hui-Jing Li、Xiang Nan、Ying Liu、Yan-Chao Wu

  DOI：10.1055/s-0039-1690002

  日期：2019.10

  N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide

  抽象的 N-磺酰基-和N-酰基吡咯是通过二烯丙基胺的烯烃闭环易位和在钌Grubbs催化剂和合适的铜催化剂的存在下原位氧化芳构化而合成的。在Cu（OTf）2和CuBr 2的存在下，反应在一锅中分别得到N-磺酰基-和N-酰基吡咯。在氧气气氛下，不需要氢过氧化物氧化剂即可使反应顺利进行。该方案具有许多优点，例如使用无害氧化剂和易于获得的起始原料，在一个锅中操作，并显示出广泛的底物范围。 N-磺酰基-和N-酰基吡咯是通过二烯丙基胺的烯烃闭环易位和在钌Grubbs催化剂和合适的铜催化剂的存在下原位氧化芳构化而合成的。在Cu（OTf）2和CuBr 2的存在下，反应在一锅中分别得到N-磺酰基-和N-酰基吡咯。在氧气气氛下，不需要氢过氧化物氧化剂即可使反应顺利进行。该方案具有许多优点，例如使用无害氧化剂和易于获得的起始原料，在一个锅中操作，并显示出广泛的底物范围。
• Metal‐Catalyzed Organic Reactions by Resonant Acoustic Mixing**
  作者：Lori Gonnet、Cameron B. Lennox、Jean‐Louis Do、Ivani Malvestiti、Stefan G. Koenig、Karthik Nagapudi、Tomislav Friščić

  DOI：10.1002/anie.202115030

  日期：2022.3.21

  Resonant Acoustic Mixing (RAM) enables mechanochemical organic synthesis that avoids milling or crushing media, as well as bulk solvents. The RAM methodology enables significant simplification and improvement of mechanochemical olefin metathesis, the first mechanochemical strategy for ene-yne metathesis, and permits the direct, 200-fold scaling-up of the mechanochemical synthesis of pharmaceutically

  共振声学混合 (RAM) 可实现机械化学有机合成，避免研磨或粉碎介质以及大量溶剂。RAM 方法能够显着简化和改进机械化学烯烃复分解，这是烯-炔复分解的第一个机械化学策略，并允许将药学活性磺酰脲的机械化学合成直接放大 200 倍，而无需对反应条件进行任何重大改变或转换。
• Process for the production of oxabispidines
  申请人：Pavey John

  公开号：US06936712B1

  公开（公告）日：2005-08-30

  There is provided a process for the preparation of a compound of formula I, (I), or a pharmaceutically acceptable derivative thereof, wherein A, B, G, R 1 , R 2 , R 3 , R 4 and R 41 to R 46 have meanings given in the description, which process comprises the dehydrative cyclisaton of a compound of formula II, (II).

  提供了一种制备式I化合物或其药学上可接受的衍生物的方法，其中A、B、G、R1、R2、R3、R4和R41到R46具有描述中给出的含义，该方法包括式II化合物的脱水环化反应（II）。

表征谱图