[N-(2-nitrophenylsulfonyl)imino]phenyliodinane | 934282-04-9

• 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-(2-nitrophenylsulfonyl)imino]phenyliodinane
• 英文别名: 2-nitro-N-(phenyl-λ³-iodanylidene)benzene sulfonamide；[N-(o-nitrophenylsulfonyl)imino]phenyliodinane；2-nitro-N-(phenyl-lambda3-iodanylidene)benzenesulfonamide；2-nitro-N-(phenyl-λ3-iodanylidene)benzenesulfonamide
• CAS: 934282-04-9
• 化学式: C₁₂H₉IN₂O₄S
• 分子量: 404.185
• InChiKey: AJGVZXCPXDYLDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [N-(2-nitrophenylsulfonyl)imino]phenyliodinane 在 Cu(OTf)₂ 、 sodium hydride 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 5.25h， 生成 (R)-trans-N-(1-(4-aminocyclohexyl)-2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)-2-nitrobenzenesulfonamide
  参考文献：
  名称：

  Optimization of physicochemical properties and safety profile of novel bacterial topoisomerase type II inhibitors (NBTIs) with activity against Pseudomonas aeruginosa

  摘要：

  Type II bacterial topoisomerases are well validated targets for antimicrobial chemotherapy. Novel bacterial type II topoisomerase inhibitors (NBTIs) of these targets are of interest for the development of new antibacterial agents that are not impacted by target-mediated cross-resistance with fluoroquinolones. We now disclose the optimization of a class of NBTIs towards Gram-negative pathogens, especially against drug-resistant Pseudomonas aeruginosa. Physicochemical properties (pKa and logD) were optimized for activity against P. aeruginosa and for reduced inhibition of the hERG channel. The optimized analogs 9g and 9i displayed potent antibacterial activity against P. aeruginosa, and a significantly improved hERG profile over previously reported analogs. Compound 9g showed an improved QT profile in in vivo models and lower clearance in rat over earlier compounds. The compounds show promise for the development of new antimicrobial agents against drug-resistant Pseudomonas aeruginosa.

  DOI：

  10.1016/j.bmc.2014.07.040
• 作为产物：
  描述：

  碘苯二乙酸 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.34h， 以68%的产率得到[N-(2-nitrophenylsulfonyl)imino]phenyliodinane
  参考文献：
  名称：

  WO2006/101860

  摘要：

  公开号：

文献信息

• Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
  作者：Daichi Kawauchi、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1002/ejoc.201900088

  日期：2019.3.14

  Various C–C and C‐X bonds could be formed by double functionalization of olefins featuring Cu‐mediated assisted tandem catalysis. Furthermore, one‐pot indoline syntheses with o‐bromostyrenes as an application could be achieved.

  通过具有铜介导的辅助串联催化作用的烯烃的双重官能化，可以形成各种C–C和C–X键。此外，可以实现与邻溴苯乙烯的一锅二氢吲哚合成。
• A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers
  作者：Tadashi Oohara、Hisanori Nambu、Masahiro Anada、Koji Takeda、Shunichi Hashimoto

  DOI：10.1002/adsc.201200219

  日期：2012.8.13

  copolymerization of a dirhodium(II) complex-containing monomer with styrene and 1,6-bis(4-vinylbenzyloxy)hexane as a flexible cross-linker. The polymer-supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh) to provide α-amino ketones in high yields with high levels of enantioselectivity and could be used

  四（N-四氟邻苯二甲酰基- （S）-叔亮氨酸酯] [Rh 2（S -TFPTTL）4 ]的四氢吡啶鎓（II）的固定化是通过将含二氢吡啶鎓（II）配合物的单体与苯乙烯共聚完成的。和1,6-双（4-乙烯基苄氧基）己烷作为柔性交联剂。聚合物负载的手性氟化二氢吡啶鎓（II）配合物催化甲硅烷基烯醇醚与[ N-（2-硝基苯基磺酰基）亚氨基]苯基碘丁烷（NsNIPh）的胺化反应，以高收率和高对映选择性提供α-氨基酮。在固体反应物的存在下，催化剂的使用量高达20倍，很容易经受住搅拌。
• Synthesis of β-alkoxy-<i>N</i>-protected phenethylamines <i>via</i> one-pot copper-catalyzed aziridination and ring opening
  作者：Jorge Saavedra-Olavarría、Matías Madrid-Rojas、Iriux Almodovar、Patricio Hermosilla-Ibáñez、Edwin G. Pérez

  DOI：10.1039/c8ra03815e

  日期：——

  one-pot aminoalkoxylation of styrenes using primary and secondary alcohols and three different iminoiodanes as alkoxy and nitrogen sources respectively, is reported. The β-alkoxy-N-protected phenethylamines obtained were used to synthesise β-alkoxy-N-benzylphenethylamines which are interesting new compounds that could act as possible neuronal ligands.

  报道了分别使用伯醇和仲醇以及三种不同的亚氨基碘烷作为烷氧基和氮源的苯乙烯区域选择性、铜催化的一锅氨基烷氧基化反应。获得的 β-烷氧基-N-保护的苯乙胺用于合成 β-烷氧基-N-苄基苯乙胺，这是一种有趣的新化合物，可以作为可能的神经元配体。
• Palladium-catalyzed carbonylation of (arylsulfonyliminoiodo)benzenes to arylsulfonyl isocyanates
  作者：Gábor Besenyei、László I. Simándi

  DOI：10.1016/s0040-4039(00)73576-3

  日期：1993.4

  In the presence of palladium complexes as catalysts, carbonylation of (arylsulfonyliminoiodo)benzenes to arylsulfonyl isocyanates can be accomplished with 50–80% yield.

  在钯络合物作为催化剂的存在下，可以将（芳基磺酰亚胺基碘）苯羰基化为芳基磺酰基异氰酸酯，产率为50-80％。
• Synthesis of the Oxygenated Pactamycin Core
  作者：Spencer Knapp、Younong Yu

  DOI：10.1021/ol0702472

  日期：2007.3.1

  [structure: see text]. Pactamycin, one of the most complex and densely functionalized aminocyclitol antibiotics known, presents synthetic challenges that include reactivity and sterics, relative and absolute stereochemistry, and functional group compatibility and protection. An approach is reported that features four different types of (cyclopentane) face selective functionalization reactions and results

  [结构：见文字]。泛霉素是已知的最复杂，功能最密集的氨基环醇抗生素之一，它在合成方面面临挑战，包括反应性和空间位阻，相对和绝对立体化学以及官能团的相容性和保护作用。据报道，一种方法具有四种不同类型的（环戊烷）表面选择性官能化反应，可产生多官能化且经过适当保护的中间体，该中间体结合了目标的所有核心碳原子和氧化官能团。