N-(adamantan-1-ylmethyl)phthalimide | 313231-15-1

• 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: N-(adamantan-1-ylmethyl)phthalimide
• 英文别名: N-(1-adamantylmethyl)phthalimide；2-(1-Adamantylmethyl)isoindoline-1,3-dione；2-(1-adamantylmethyl)isoindole-1,3-dione
• CAS: 313231-15-1
• 化学式: C₁₉H₂₁NO₂
• mdl: MFCD00220389
• 分子量: 295.381
• InChiKey: NFKMLGTZGWTJTG-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C(Solv: methanol (67-56-1))
• 沸点：
  427.5±14.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(adamantan-1-ylmethyl)phthalimide 在 肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 1-金刚烷甲胺
  参考文献：
  名称：

  Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones

  摘要：

  A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 mu M). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 mu M) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 mu M, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 mu M, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.039
• 作为产物：
  描述：

  苯酐 、 1-金刚烷甲胺 反应 0.33h， 以59%的产率得到N-(adamantan-1-ylmethyl)phthalimide
  参考文献：
  名称：

  N-（金刚烷基）邻苯二甲酰亚胺中光诱导氢原子的提取：固态的结构反应性研究

  摘要：

  合成了金刚烷基官能化的邻苯二甲酰亚胺，并通过X射线晶体学分析分析了固态下分子内光化学氢原子提取的可能性。这些分析和固态光解显示，确定固态典型羰基化合物的光化学反应性的参数也可以扩展到邻苯二甲酰亚胺。仅N-（2-金刚烷基）邻苯二甲酰亚胺进行了固态光化学反应，这是邻苯二甲酰亚胺系列中的第一个例子。该反应是区域和立体选择性的，产生内醇。另一方面，N-（2-金刚烷基）邻苯二甲酰亚胺在溶液中的光反应产生了以exo-醇为主要产物的化合物。内醇和苯并ze庚二酮。

  DOI：

  10.1016/j.tet.2008.12.010

文献信息

• Photoinitiated Domino Reactions: <i>N</i>-(Adamantyl)phthalimides and <i>N</i>-(Adamantylalkyl)phthalimides
  作者：Margareta Horvat、Helmut Görner、Klaus-Dieter Warzecha、Jörg Neudörfl、Axel G. Griesbeck、Kata Mlinarić-Majerski、Nikola Basarić

  DOI：10.1021/jo901753z

  日期：2009.11.6

  was observed with phthalimides 1, 3, and 6 and delivered stereospecifically the hexacyclic benzazepine products 12, 19, and 27, respectively. The lowest triplet states of 1−6 were characterized in several solvents upon direct and acetone-sensitized excitation. The intermolecular electron transfer from triethylamine and DABCO was studied, and the radical anions were observed. Electrochemical measurements

  邻苯二甲酰亚胺1 - 6后经历直接照射的光化学反应以及三重态敏化和产生新的产品。除了形成初级光产物之外，第一光化学步骤还引发随后的热多米诺反应或热和光化学反应的多米诺序列。后者，涉及两个分子内光化学γ-H抽象，用邻苯二甲酰亚胺观察到1，3，和6和立体特异性递送的六环苯并氮杂产品12，19，和27分别。最低三重态1 − 6在直接和丙酮敏化的激发下，在几种溶剂中进行了表征。研究了三乙胺和DABCO的分子间电子转移，并观察了自由基阴离子。电化学测量表明从的金刚烷基即分子内电子转移1 - 6到邻苯二甲酰亚胺的最低三重态状态是不可行的。产物的形成可以通过从（烷基）金刚烷到激发的邻苯二甲酰亚胺的分子内H-吸收，可以是激发的单重态或隐藏的上激发三重态。
• Antiproliferative and Antiviral Activity of Three Libraries of Adamantane Derivatives
  作者：Nikola Basarić、Margareta Sohora、Nikola Cindro、Kata Mlinarić-Majerski、Erik De Clercq、Jan Balzarini

  DOI：10.1002/ardp.201300345

  日期：2014.5

  Three libraries of adamantane derivatives were synthesized and evaluated for antiviral and antiproliferative activities against a broad variety of DNA and RNA viruses. Whereas none of the compounds exhibit antiviral activity at subtoxic concentrations, antiproliferative activity was found against murine leukemia cells (L1210), human T‐lymphocyte cells (CEM), and cervix carcinoma cells (HeLa) for 4

  合成了三个金刚烷衍生物文库，并评估了针对多种 DNA 和 RNA 病毒的抗病毒和抗增殖活性。虽然这些化合物在亚毒浓度下均不表现出抗病毒活性，但在 4、8 和 10 年中发现对鼠白血病细胞 (L1210)、人 T 淋巴细胞 (CEM) 和宫颈癌细胞 (HeLa) 具有抗增殖活性。
• Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones
  作者：Jan Balzarini、Barbara Orzeszko-Krzesińska、Jan K. Maurin、Andrzej Orzeszko

  DOI：10.1016/j.ejmech.2008.02.039

  日期：2009.1

  A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 mu M). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 mu M) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 mu M, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 mu M, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: structure–reactivity study in the solid state
  作者：Nikola Basarić、Margareta Horvat、Oliver Franković、Kata Mlinarić-Majerski、Jörg Neudörfl、Axel G. Griesbeck

  DOI：10.1016/j.tet.2008.12.010

  日期：2009.2

  intramolecular photochemical hydrogen atom abstraction in the solid state analyzed by X-ray crystallographic analyses. These analyses and solid-state photolyses showed that the parameters determining photochemical reactivity for typical carbonyl compounds in the solid state can also be extended to phthalimides. Only N-(2-adamantyl)phthalimide underwent a solid-state photochemical reaction, which is the

  合成了金刚烷基官能化的邻苯二甲酰亚胺，并通过X射线晶体学分析分析了固态下分子内光化学氢原子提取的可能性。这些分析和固态光解显示，确定固态典型羰基化合物的光化学反应性的参数也可以扩展到邻苯二甲酰亚胺。仅N-（2-金刚烷基）邻苯二甲酰亚胺进行了固态光化学反应，这是邻苯二甲酰亚胺系列中的第一个例子。该反应是区域和立体选择性的，产生内醇。另一方面，N-（2-金刚烷基）邻苯二甲酰亚胺在溶液中的光反应产生了以exo-醇为主要产物的化合物。内醇和苯并ze庚二酮。