N-(2-iodobenzyl)-4-methoxyaniline | 1220282-38-1

• 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-iodobenzyl)-4-methoxyaniline
• 英文别名: N-(p-methoxylphenyl)-N-(o-iodobenzyl)amine；N-(2-iodobenzyl)-4-methoxybenzenamine；N-[(2-iodophenyl)methyl]-4-methoxyaniline
• CAS: 1220282-38-1
• 化学式: C₁₄H₁₄INO
• 分子量: 339.176
• InChiKey: SBYVWNWRILPNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-iodobenzyl)-4-methoxyaniline 在 potassium tert-butylate 作用下， 以 氨 为溶剂， 反应 2.0h， 以95%的产率得到2-methoxyphenanthridine
  参考文献：
  名称：

  Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis

  摘要：

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.

  DOI：

  10.1021/jo9025918
• 作为产物：
  描述：

  邻碘氯苄 、 甲氧苯胺 在 potassium carbonate 、 lithium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以71%的产率得到N-(2-iodobenzyl)-4-methoxyaniline
  参考文献：
  名称：

  Selective Synthesis of Either Isoindole- or Isoindoline-1-carboxylic Acid Esters by Pd(0)-Catalyzed Enolate Arylation

  摘要：

  Two efficient palladium-catalyzed intramolecular alpha-arylation reactions of alpha-amino acid esters have been developed that allow either 1-isoindolecarboxylic acid esters or the corresponding isoindolines to be selectively synthesized simply by a slight change of reaction conditions.

  DOI：

  10.1021/jo101054j

文献信息

• Pd⁰-Catalyzed Intramolecular α-Arylation of Sulfones: Domino Reactions in the Synthesis of Functionalized Tetrahydroisoquinolines
  作者：Daniel Solé、Ferran Pérez-Janer、Raffaella Mancuso

  DOI：10.1002/chem.201406305

  日期：2015.3.16

  A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd0‐catalyzed intramolecular α‐arylation of sulfones is reported. The combination of this Pd‐catalyzed reaction with intermolecular Michael and aza‐Michael reactions allows the development of two‐ and three‐step domino processes to synthesize diversely functionalized scaffolds from readily available starting materials.

  据报道，基于Pd 0催化的砜分子内α-芳基化反应，合成四氢异喹啉的新策略。这种Pd催化反应与分子间Michael和Aza-Michael反应的结合使得可以开发两步和三步的多米诺骨牌工艺，以从容易获得的起始原料合成功能多样的支架。
• Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
  作者：Ping-Xin Zhou、Jian-Yi Luo、Lian-Biao Zhao、Yu-Ying Ye、Yong-Min Liang

  DOI：10.1039/c3cc40577j

  日期：——

  Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.

  吲哚啉是通过钯催化的N-(2-碘苄基)苯胺与α,β-不饱和N-对甲苯磺酰腙的偶联反应合成的。该反应具有几个潜在优势：(1) 对多种官能团具有耐受性，(2) 操作简便且条件温和，(3) 丰富了吲哚啉类化合物，(4) 一步形成两个新键。
• A practical method for N-cyanation of secondary amines and sulfonamides
  作者：Zhaojun Hang、Xiaowei Tong、Zuowa Li、Zhao-yan Wang、Weihua Xue

  DOI：10.1016/j.tetlet.2021.153564

  日期：2022.1

  Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl

  氰胺是一类重要的分子。这项工作描述了双取代氰胺的简便合成。在这里，容易获得的 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) 被用作稳定的亲电氰化试剂。多种仲胺被有效地氰化。此外，仲磺酰胺被证明是合适的底物，并且很容易转化为N-烷基（芳基）-N-芳基磺酰基-氰胺，作为有机转化的重要组成部分。
• Supported-Pd catalyzed carbonylative synthesis of phthalimides and isoindolinones using Oxalic acid as in situ CO surrogate with 2-iodobenzamides and 2-iodobenzylanilines in ppm-level catalyst loading
  作者：Shankar Ram、Pushkar Mehara、Ashish Kumar、Ajay Kumar Sharma、Arvind Singh Chauhan、Ajay Kumar、Pralay Das

  DOI：10.1016/j.mcat.2022.112606

  日期：2022.9