N-(2-iodophenyl)-N,4-dimethylbenzenesulfonamide | 56751-80-5

• 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-iodophenyl)-N,4-dimethylbenzenesulfonamide
• 英文别名: Benzenesulfonamide, N-(2-iodophenyl)-N,4-dimethyl-
• CAS: 56751-80-5
• 化学式: C₁₄H₁₄INO₂S
• 分子量: 387.241
• InChiKey: UUOSIARSXQLWRW-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  446.8±55.0 °C(Predicted)
• 密度：
  1.644±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-iodophenyl)-N,4-dimethylbenzenesulfonamide 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 以81%的产率得到N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Preparation, X-ray Structure, and Oxidative Reactivity of N-(2-Iodylphenyl)tosylamides and 2-Iodylphenyl Tosylate: Iodylarenes Stabilized by Ortho-Substitution with a Sulfonyl Group

  摘要：

  New tosyl derivatives of 2-iodylaniline and 2-iodylphenol were prepared by the dimethyldloxirane oxidation of the corresponding 2-iodophenyltosylamides or 2-iodophenyl tosylate and isolated as stable, microcrystalline products. Single-crystal X-ray diffraction analysis of N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide revealed pseudocyclic structure formed by intramolecular 1 center dot center dot center dot O interactions between the hypervalent iodine center and the sulfonyl oxygens in the tosyl group. This tosylamide has an excellent solubility in organic solvents and is it potentially useful hypervalent iodine oxidant.

  DOI：

  10.1021/jo901638f
• 作为产物：
  描述：

  N-Boc-2-碘苯胺 在 吡啶 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 N-(2-iodophenyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  通过钯/降冰片烯协同催化的CH-H胺化/芳构化，酸促进胺基二苯并sultams的快速合成

  摘要：

  本文我们报道的协议访问胺化苯并稠通过顺序磺内酰胺邻-amination，随后本位经由钯/降冰片烯coorperative催化芳基碘化物轴承磺酰胺官能团的-arylation。该反应在温和条件下以中等到良好的效率展示了广泛的底物范围。

  DOI：

  10.1002/adsc.202001413

文献信息

• Synthesis of biaryls via intramolecular free radical ipso-substitution reactions
  作者：Feroze Ujjainwalla、Maria Lucília E.N. da Mata、Andrew M.K. Pennell、Carmen Escolano、William B. Motherwell、Santiago Vázquez

  DOI：10.1016/j.tet.2015.07.048

  日期：2015.9

  intramolecular free radical [1,5]-ipso-substitution using sulfonamide and sulfonate derived tethering chains. The overall efficiency of the process is determined by appropriately positioned substituents on the aromatic acceptor ring. The extension of the process to benzylic sulfonates and their corresponding N-methylsulfonamide alternatives as substrates in potential [1,6]-ipso-substitution reactions leads

  使用磺酰胺和磺酸酯衍生的束缚链，通过分子内自由基[1,5] -ipso取代制备各种官能化的联芳基和杂联芳基。该方法的总效率由芳族受体环上适当定位的取代基决定。该方法的扩展来苄基磺酸酯和它们的相应Ñ -methylsulfonamide替代作为底物在潜在[1,6] -本位3'-取代反应引线主要以替代[1,7]加成产物。
• Aniline‐Type Hypervalent Iodine(III) for Intramolecular Cyclization via C−H Bond Abstraction of Hydrocarbons Containing N‐ and O‐Nucleophiles
  作者：Yuna Nishiguchi、Katsuhiko Moriyama

  DOI：10.1002/adsc.202100316

  日期：2021.7

  We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C−H bond abstraction, such as the Hofmann-Löffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields.

  我们开发了一种制备（二乙酰氧基碘）-2-（N-烷基酰胺基）苯作为苯胺型高价碘 (III) 的方法。我们还通过 C−H 键提取实现了直接环化，例如 Hofmann-Löffler-Freytag 反应、直接胺化和直接内酯化，使用苯胺型高价碘 (III) 以高产率获得相应的产物。
• Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N–S Bond Cleavage Strategy
  作者：Bo-Sheng Zhang、Fan Wang、Xue-Ya Gou、Ying-Hui Yang、Wan-Yuan Jia、Yong-Min Liang、Xi-Cun Wang、Yuke Li、Zheng-Jun Quan

  DOI：10.1021/acs.orglett.1c02715

  日期：2021.10.1

  bond cleavage with vinyl palladium, thus achieving a highly selective C–N coupling reaction in the Catallani–Lautens reaction system. On the basis of this discovery, a one-step synthesis of highly functionalized tricyclic indole derivatives was realized.

  在钯/降冰片烯 (Pd/NBE) 化学中，“邻位效应”已被证明是消除 β-碳以挤出 NBE 过程中的关键因素。在此，我们发现被对甲氧基苯磺酰基保护的邻碘苯胺可以恢复“邻位效应”，然后与乙烯基钯发生 N-S 键断裂，从而在 Catallani-Lautens 中实现高选择性的 C-N 偶联反应反应系统。在此发现的基础上，实现了高度官能化的三环吲哚衍生物的一步合成。
• A novel route to biaryls via intramolecular free radical ipso substitution reactions
  作者：William B. Motherwell、Andrew M. K. Pennell

  DOI：10.1039/c39910000877

  日期：——

  A variety of usefully functionalised biaryls may be prepared under neutral conditions by an intramolecular free radical ipso substitution reaction at an sp2 sulphonyl substituted carbon atom; the overall efficiency of the process being determined both by the nature and number of atoms linking the two aromatic rings and by appropriately positioned substituents on the aromatic aceeptor ring.

  可以在中性条件下通过sp 2磺酰基取代的碳原子上的分子内自由基ipso取代反应制备各种有用的官能化联芳基；该方法的总效率取决于连接两个芳环的原子的性质和数量以及芳族乙酰对映体环上适当放置的取代基。
• A Convergent Synthesis of Polysubstituted Aromatic Nitriles via Palladium-Catalyzed C−H Functionalization
  作者：Brian Mariampillai、Julien Alliot、Mengzhou Li、Mark Lautens

  DOI：10.1021/ja075599i

  日期：2007.12.1

  A palladium-catalyzed C-H functionalization reaction for the synthesis of highly substituted aromatic nitriles is reported. The modularity of the reaction is demonstrated by the broad range of aryl iodides which can be coupled with metal cyanides and alkyl halides or aryl bromides.

  报道了一种钯催化的 CH 官能化反应，用于合成高度取代的芳香腈。广泛的芳基碘化物可以与金属氰化物和烷基卤化物或芳基溴化物偶联，证明了该反应的模块化。