tert-butyl (1,3-dioxo-2-phenylisoindolin-4-yl)carbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl (1,3-dioxo-2-phenylisoindolin-4-yl)carbamate
• 英文别名: tert-butyl(1,3-dioxo-2-phenylisoindolin-4-yl)carbamate；tert-butyl N-(1,3-dioxo-2-phenylisoindol-4-yl)carbamate
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: NNWTZDNLSABOFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[4-三氟甲基嘧啶-2-基]乙二胺 以 甲苯 为溶剂， 反应 14.0h， 生成 tert-butyl (1,3-dioxo-2-phenylisoindolin-4-yl)carbamate
  参考文献：
  名称：

  Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines

  摘要：

  5-Amino-2-furancarboxylic acid methyl ester undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to afford ring-opened cycloadducts that are readily dehydrated using BF3 . OEt2 to give polysubstituted anilines. In each case, the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group being located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the furanamine and the LUMO of the dienophile. The atomic coefficient at the ester carbon of the furan is larger than that at the amino center, and this nicely accommodates the observed regioselectivity. The [4 + 2]-cycloaddition of N-(5-nitrofuranyl)morpholine with methyl vinyl ketone affords a mixture of three phenols. One of the phenols is derived from a Diels-Alder reaction followed by nitro group ejection and subsequent aromatization. The remaining two phenols are the result of cleavage of the initially formed oxabicyclic intermediate with concomitant migration of the nitro group. The mild reaction conditions with which furan-2-carbamic acid tert-butyl ester undergoes Diels-Alder cycloaddition with N-phenylmaleimide allow for the ready isolation of the initial oxybridged cycloadduct.

  DOI：

  10.1021/jo9702599

文献信息

• A Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of<i>N</i>-Substituted Phthalimides from Isocyanates and Benzoic Acids
  作者：Xian-Ying Shi、Andrea Renzetti、Soumen Kundu、Chao-Jun Li

  DOI：10.1002/adsc.201300834

  日期：2014.3.10

  A rhodium(III)‐catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho CH bond followed by intramolecular cyclization is described. This cascade cyclization affords N‐substituted phthalimides in one step in 26–91% yields. The reaction is highly atom‐economical, since no theoretical waste except for water is generated in the reaction.

  苯甲酸和异氰酸酯之间的铑（III）催化的酰胺化通过一个的直接官能邻Ç  H键，随后分子内环化进行说明。这种级联环化一步即可提供N取代的邻苯二甲酰亚胺，产率为26-91％。该反应是高度原子经济的，因为在反应中除水外没有产生理论上的浪费。
• Ruthenium(II)-catalyzed N-substituted phthalimide synthesis via C–H activation/[3+2] annulation
  作者：Xue-Fen Dong、Juan Fan、Xian-Ying Shi、Ke-Yan Liu、Peng-Min Wang、Jun-Fa Wei

  DOI：10.1016/j.jorganchem.2014.12.016

  日期：2015.3

  intermolecular [3 + 2] annulation pathway for aromatic acids with isocyanates to afford N-substituted phthalimide in one step is demonstrated, which provides an efficient process to direct preparation of phthalimide from commercially available starting materials and environmentally benign catalysts. This cascade cyclization involves the direct functionalization of an ortho C–H bond and the subsequent

  一步一步证明了钌催化的芳香酸与异氰酸酯的分子间[3 + 2]环化路径，可在一步中得到N-取代的邻苯二甲酰亚胺，它提供了一种有效的方法，可从市售的起始原料和环境友好的催化剂中直接制备邻苯二甲酰亚胺。这种级联环化涉及邻C–H键的直接功能化以及随后的分子内亲核取代。除了在反应中产生水以外，没有理论上的浪费。
• Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines
  作者：Albert Padwa、Martin Dimitroff、Alex G. Waterson、Tianhua Wu

  DOI：10.1021/jo9702599

  日期：1997.6.13

  5-Amino-2-furancarboxylic acid methyl ester undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to afford ring-opened cycloadducts that are readily dehydrated using BF3 . OEt2 to give polysubstituted anilines. In each case, the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group being located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the furanamine and the LUMO of the dienophile. The atomic coefficient at the ester carbon of the furan is larger than that at the amino center, and this nicely accommodates the observed regioselectivity. The [4 + 2]-cycloaddition of N-(5-nitrofuranyl)morpholine with methyl vinyl ketone affords a mixture of three phenols. One of the phenols is derived from a Diels-Alder reaction followed by nitro group ejection and subsequent aromatization. The remaining two phenols are the result of cleavage of the initially formed oxabicyclic intermediate with concomitant migration of the nitro group. The mild reaction conditions with which furan-2-carbamic acid tert-butyl ester undergoes Diels-Alder cycloaddition with N-phenylmaleimide allow for the ready isolation of the initial oxybridged cycloadduct.