2-(2-methoxycarbonylbenzyl)phthalimide | 189949-64-2

• 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: 2-(2-methoxycarbonylbenzyl)phthalimide
• 英文别名: methyl 2-((1,3-dioxoisoindolin-2-yl)methyl)benzoate；Methyl 2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoate；methyl 2-[(1,3-dioxoisoindol-2-yl)methyl]benzoate
• CAS: 189949-64-2
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: KVYRLJVVYPRMAW-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C(Solv: ethanol (64-17-5))
• 沸点：
  471.3±38.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methoxycarbonylbenzyl)phthalimide 在 肼 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 methyl 2-(aminomethyl)benzoate
  参考文献：
  名称：

  NOVEL NITROGENOUS COMPOUND AND USE THEREOF

  摘要：

  一种新型含氮化合物，对HIV病毒感染性疾病、风湿病和癌细胞转移等疾病具有有效作用。它是一种由下述通用式(1)表示的含氮化合物。在该式中，A通常表示由式(2)表示的基团（A1是氢或可选择取代的单环或多环杂环芳香环；G1是单键或由下述式(3)表示的碳氢基团，其中R1、R2和R3可能是可选择取代的碳氢基团）；W是可选择取代的碳氢基团或杂环环；x是-C(=O)NH-；y是-C(=O)-；D1是氢原子、具有多环芳香环的烷基、二（取代烷基）胺或脂环胺。

  公开号：

  EP1431290A1
• 作为产物：
  描述：

  2-溴甲基苯甲酸甲酯 、 邻苯二甲酸亚胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-methoxycarbonylbenzyl)phthalimide
  参考文献：
  名称：

  Synthesis of benzo(or furo)[5,6]azepino[2,1-a]isoindolone derivatives: π-cyclisations of N-acyliminium ions

  摘要：

  Benzo(or furo)[5,6]azepino[2,1-a]isoindolone and derivatives were obtained easily in one-pot via N-acyliminium ions by treatment of 2-(2-methoxycarbonylbenzyl(or fur-3-yl))phthalimide with alkylmagnesium iodide followed by an acidic hydrolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02075-9

文献信息

• Evaluation of<i>N</i>-hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core<i>via</i>an intramolecular π and<i>O</i>-cationic cyclization
  作者：Armelle Cul、Anthony Pesquet、Adam Daïch、Abderrahim Chihab-Eddine、Štefan Marchalín

  DOI：10.1002/jhet.5570400314

  日期：2003.5

  isoindolo[1,3]benzo(or thieno)oxazepines 8a,b and one of their positional isomers aromatic tricyclic N,O-acetals 13b are reported to occur efficiently in a three-step sequence from N-hydroxy-methylphthalimide (6). The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic N-acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam

  据报道，熔融的异吲哚并[1,3]苯并（或噻吩）恶氮杂ze烷8a，b及其位置异构体之一是芳香族三环N，O-缩醛13b以三步顺序有效地从N-羟基-甲基邻苯二甲酰亚胺发生（6）。该方法的关键步骤是环内和/或环外N-酰亚胺阳离子的分子内芳基化。讨论了导致这些物种，特别是导致三环内酰胺13b的机理。
• Reductive intramolecular coupling of phthalimides with esters and ketones by low-valent titanium
  作者：Naoki Kise、Tatsuhiro Manto、Toshihiko Sakurai

  DOI：10.1016/j.tet.2020.131725

  日期：2020.12

  The reductive intermolecular coupling of phthalimides with esters by low-valent titanium gave five-, six-, and seven-membered cyclized products as α-hydroxyketones and their further reduced ketones. The obtained cyclized products were transformed to alkylideneisoindolin-1-ones. The reductive intermolecular coupling of phthalimides with ketones by low-valent titanium also gave five-, six-, and seven-membered

  低价钛将邻苯二甲酰亚胺与酯进行还原性分子间偶联，得到五元，六元和七元环化产物，为α-羟基酮，并进一步还原为酮。将获得的环化产物转化为亚烷基异吲哚啉-1-酮。低价钛将邻苯二甲酰亚胺与酮进行还原性分子间偶联，也一步一步得到了五元，六元和七元环化产物，即亚烷基异吲哚啉-1-酮。
• Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines
  作者：Pascal Pigeon、Mohamed Othman、Pierre Netchitailo、Bernard Decroix

  DOI：10.1016/s0040-4020(97)10359-3

  日期：1998.2

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A New Access to Isoindolo[2,1-b][2,4]benzodiazepines through an N-Acyliminium Ion - Amide Cyclization
  作者：Pascal Pigeon、Bernard Decroix

  DOI：10.1016/s0040-4039(97)00539-x

  日期：1997.4

  Isoindolo[2,1-b][2,4]benzodiazepines 11a-c were synthesized from hydroxylactam-acid 5 when it was treated successively with thionyl chloride, ammonia (or an alkylamine) and p-toluenesulfonic acid. (C) 1997 Elsevier Science Ltd.
• NOVEL NITROGENOUS COMPOUND AND USE THEREOF
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP1431290A1

  公开（公告）日：2004-06-23

  A novel nitrogen-containing compound effective against diseases such as HIV viral infectious diseases, rheumatism, and cancerous metastasis. It is a nitrogen-containing compound represented by the following general formula (1). In the formula, A typically represents a group represented by the formula (2) (A1 is hydrogen or an optionally substituted, mono- or polycyclic, heteroaromatic or aromatic ring; G1 is a single bond or a hydrocarbon group represented by the following formula (3) wherein R1, R2, and R3 may be optionally substituted hydrocarbon groups); W is an optionally substituted hydrocarbon group or heterocyclic ring; x is -C(=O)NH-; y is -C(=O)-; and D1 is hydrogen atom, alkyl having a polycyclic aromatic ring, di (substituted alkyl)amine, or alicyclic amine.

  一种新型含氮化合物，对HIV病毒感染性疾病、风湿病和癌细胞转移等疾病具有有效作用。它是一种由下述通用式(1)表示的含氮化合物。在该式中，A通常表示由式(2)表示的基团（A1是氢或可选择取代的单环或多环杂环芳香环；G1是单键或由下述式(3)表示的碳氢基团，其中R1、R2和R3可能是可选择取代的碳氢基团）；W是可选择取代的碳氢基团或杂环环；x是-C(=O)NH-；y是-C(=O)-；D1是氢原子、具有多环芳香环的烷基、二（取代烷基）胺或脂环胺。