N-(1-环丙基-1-苯基甲氧基)邻苯二甲酰亚胺 | 1034621-83-4

• 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
• 中文名称: N-(1-环丙基-1-苯基甲氧基)邻苯二甲酰亚胺
• 英文名称: N-(1-cyclopropyl-1-phenylmethoxy)phthalimide
• 英文别名: 2-[Cyclopropyl(phenyl)methoxy]isoindole-1,3-dione
• CAS: 1034621-83-4
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: LDNRYRWJUDCUAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  447.6±38.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-环丙基-1-苯基甲氧基)邻苯二甲酰亚胺 在 lithium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 氘代丙酮 为溶剂， 反应 4.0h， 以34%的产率得到苯基环丙基甲酮
  参考文献：
  名称：

  N-烷氧基邻苯二甲酰亚胺的光诱导电子转移促进的氧化还原断裂

  摘要：

  已经开发了一种新的光诱导的N-烷氧基邻苯二甲酰亚胺电子转移促进的氧化还原片段化。机理实验已经确定，该反应通过独特的协同分子内断裂过程进行。这种独特的机理赋予了许多合成优势，这些优势在各种杂环底物的氧化还原片段化中得到了彰显。

  DOI：

  10.1021/ol202740w
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 环丙基苯基碳酸酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-(1-环丙基-1-苯基甲氧基)邻苯二甲酰亚胺
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028

文献信息

• Cu-Facilitated C−O Bond Formation Using <i>N</i>-Hydroxyphthalimide: Efficient and Selective Functionalization of Benzyl and Allylic C−H Bonds
  作者：Ji Min Lee、Eun Ju Park、Seung Hwan Cho、Sukbok Chang

  DOI：10.1021/ja8031218

  日期：2008.6.1

  A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and Phl(OAc)(2) in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.