4-Monophenyl-amino-N-methylphthalimide | 4636-67-3

• 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: 4-Monophenyl-amino-N-methylphthalimide
• 英文别名: 4-Monophenylamino-N-methylphthalimid；5-anilino-2-methylisoindole-1,3-dione
• CAS: 4636-67-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: DAHJVNUHBMYWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Monophenyl-amino-N-methylphthalimide 在 potassium acetate 、 一氯化碘 、 溶剂黄146 作用下， 反应 30.0h， 以97%的产率得到4-(4'-iodophenylamino)-N-methylphthalimide
  参考文献：
  名称：

  基于 4-氨基-N-甲基邻苯二甲酰亚胺和光致变色二芳基乙烯的可切换荧光和溶剂致变色分子探针

  摘要：

  新的荧光光致变色化合物（1-H 和 1-Boc）已在不同溶剂中合成和表征。通过光致变色反应，荧光发射可以分别用可见光和紫外线“打开”和“关闭”。发射波长和效率在很大程度上取决于溶剂的极性。这些化合物在发射最大值中显示出正的溶剂致变色效应，并且它们的荧光量子产率随着溶剂极性的增加（从环己烷到二恶烷）而降低。在比二恶烷更具极性的溶剂中，发射太弱，因此无法检测到，因此 1-H 和 1-Boc 表现为“正常”光致变色化合物。光致变色反应对环境也很敏感。与环己烷相比，乙醇中 1-H 的着色反应 (ΦOFCF) 的量子产率降低了一个数量级以上，并且在极性溶剂中观察到化合物 1-Boc 的 ΦOFCF 降低了约三倍（与非极性溶剂相比）。对于这两种化合物，发现开环反应不依赖于溶剂。新型荧光分子开关 1-H 和 1-Boc 能够探测其微环境的极性。(© Wiley-VCH Verlag GmbH & Co.

  DOI：

  10.1002/ejoc.200800125
• 作为产物：
  描述：

  N-甲基-4-氨基邻苯二甲酰亚胺 、 碘苯 在 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以13.6%的产率得到4-Monophenyl-amino-N-methylphthalimide
  参考文献：
  名称：

  Novel anilinophthalimide derivatives as potential probes for β-amyloid plaque in the brain

  摘要：

  A group of novel 4,5-dianilinophthalimide derivatives has been synthesized in this study for potential use as beta-amyloid (A beta) plaque probes. Staining of hippocampus tissue sections from Alzheimer's disease (AD) brain with the representative compound 9 indicated selective labeling of it to A beta plaques. The binding affinity of radioiodinated [I-125]9 for AD brain homogenates was 0.21 nM (K-d), and of other derivatives ranged from 0.9 to 19.7 nM, except for N-methyl-4,5-dianilinophthalimide (K-i > 1000 nM). [I-125]9 possessed the optimal lipophilicity with Log P value of 2.16, and its in vivo biodistribution in normal mice exhibited excellent initial brain uptake (5.16% ID/g at 2 min after injection) and a fast washout rate (0.56% ID/g at 60 min). The encouraging results suggest that this novel derivative of [I-123]9 may have potential as an in vivo SPECT probe for detecting amyloid plaques in the brain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.023

文献信息

• Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions
  作者：Jose R. Cabrero-Antonino、Rosa Adam、Veronica Papa、Mattes Holsten、Kathrin Junge、Matthias Beller

  DOI：10.1039/c7sc01175j

  日期：——

  metal-catalysed reductive C2-alkoxylation of cyclic imides (phthalimides and succinimides) is presented. Crucial for the success is the use of [Co(BF4)2·6H2O/triphos (L1)] combination and no external additives are required. Using the optimal cobalt-system, the hydrogenation of the aromatic ring of the parent phthalimide is avoided and only one of the carbonyl groups is selectively functionalized. The

  提出了第一个通用且有效的非贵金属催化的环状酰亚胺（邻苯二甲酰亚胺和琥珀酰亚胺）的还原性C2-烷氧基化反应。成功的关键是使用[Co（BF 4）2 ·6H 2 O / triphos（L1）]的组合，并且不需要外部添加剂。使用最佳的钴系统，避免了母体邻苯二甲酰亚胺的芳环的氢化，并且仅羰基中的一个被选择性地官能化。所得的产物，N-和芳基环取代的3-烷氧基-2，3-二氢-1H-异吲哚-1-酮和N-取代的3-烷氧基-吡咯烷基-2-酮衍生物是在温和的条件下以良好至优异的分离产率制备的。分子内还原偶联也可以在一步法中进行，从而得到三环化合物。本协议为药物和生物学关注的功能化N杂环化合物的直接合成开辟了新的贱金属工艺开发途径。
• Novel anilinophthalimide derivatives as potential probes for β-amyloid plaque in the brain
  作者：Xin-Hong Duan、Jin-Ping Qiao、Yang Yang、Meng-Chao Cui、Jiang-Ning Zhou、Bo-Li Liu

  DOI：10.1016/j.bmc.2009.12.023

  日期：2010.2

  A group of novel 4,5-dianilinophthalimide derivatives has been synthesized in this study for potential use as beta-amyloid (A beta) plaque probes. Staining of hippocampus tissue sections from Alzheimer's disease (AD) brain with the representative compound 9 indicated selective labeling of it to A beta plaques. The binding affinity of radioiodinated [I-125]9 for AD brain homogenates was 0.21 nM (K-d), and of other derivatives ranged from 0.9 to 19.7 nM, except for N-methyl-4,5-dianilinophthalimide (K-i > 1000 nM). [I-125]9 possessed the optimal lipophilicity with Log P value of 2.16, and its in vivo biodistribution in normal mice exhibited excellent initial brain uptake (5.16% ID/g at 2 min after injection) and a fast washout rate (0.56% ID/g at 60 min). The encouraging results suggest that this novel derivative of [I-123]9 may have potential as an in vivo SPECT probe for detecting amyloid plaques in the brain. (C) 2009 Elsevier Ltd. All rights reserved.
• Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
  作者：Sergey F. Yan、Vladimir N. Belov、Mariano L. Bossi、Stefan W. Hell

  DOI：10.1002/ejoc.200800125

  日期：2008.5

  New fluorescent photochromic compounds (1-H and 1-Boc) have been synthesized and characterized in different solvents. The fluorescence emission can be switched “on” and “off” with visible light and UV, respectively, by means of the photochromic reaction. The emission wavelength and efficiency strongly depend on the polarity of the solvent. The compounds show a positive solvatochromic effect in the

  新的荧光光致变色化合物（1-H 和 1-Boc）已在不同溶剂中合成和表征。通过光致变色反应，荧光发射可以分别用可见光和紫外线“打开”和“关闭”。发射波长和效率在很大程度上取决于溶剂的极性。这些化合物在发射最大值中显示出正的溶剂致变色效应，并且它们的荧光量子产率随着溶剂极性的增加（从环己烷到二恶烷）而降低。在比二恶烷更具极性的溶剂中，发射太弱，因此无法检测到，因此 1-H 和 1-Boc 表现为“正常”光致变色化合物。光致变色反应对环境也很敏感。与环己烷相比，乙醇中 1-H 的着色反应 (ΦOFCF) 的量子产率降低了一个数量级以上，并且在极性溶剂中观察到化合物 1-Boc 的 ΦOFCF 降低了约三倍（与非极性溶剂相比）。对于这两种化合物，发现开环反应不依赖于溶剂。新型荧光分子开关 1-H 和 1-Boc 能够探测其微环境的极性。(© Wiley-VCH Verlag GmbH & Co.