2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl benzoate | 6656-84-4

• 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
• 英文名称: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl benzoate
• 英文别名: 2-phthaloylamino-1-ethyl benzoate；2-phthalimidoethyl benzoate；benzoic acid-(2-phthalimido-ethyl ester)；Benzoesaeure-(2-phthalimido-aethylester)；β-Phthalimidoethylbenzoat；2-(1,3-Dioxoisoindolin-2-yl)ethyl benzoate；2-(1,3-dioxoisoindol-2-yl)ethyl benzoate
• CAS: 6656-84-4
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: GGEJXUXPXPVWNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 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

• 作为产物：
  描述：

  苯酐 在 三乙胺 、 diethylcyclopropenone 作用下， 以 甲基叔丁基醚 、 甲苯 为溶剂， 反应 26.0h， 生成 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl benzoate
  参考文献：
  名称：

  高水平催化效率的酒精亲核取代反应

  摘要：

  介绍了一种在立体化学转化下以高催化效率对提供烷基氯化物，溴化物和碘化物的醇进行亲核取代（S N）的实用方法。二乙基环丙烯酮作为一种简单的路易斯碱有机催化剂与苯甲酰氯作为一种试剂的融合，可实现高达100的显着营业额。此外，首次证明了在转化型S N型转化中使用纯乙酰氯作为化学计量的促进剂。。操作上简单明了的协议展现出高水平的立体声选择性和可伸缩性，并且可以容忍各种功能组。

  DOI：

  10.1021/acs.orglett.8b01023

文献信息

• One-Step Transformation of Tetrahydropyranyl Ethers Using Indium(III) Triflate as the Catalyst
  作者：Tomoko Mineno、Nana Nikaido、Hisao Kansui

  DOI：10.1248/cpb.57.1167

  日期：——

  one-step transformation of tetrahydropyranyl (THP) ethers is described. According to our earlier experiments, indium(III) triflate has proven to be an efficient catalyst for the transformation of THP ethers into their corresponding acetates. In further intensive work, we have developed a useful transforming reaction of THP ethers using various anhydride moieties. Indium(III) triflate was confirmed as a suitable

  描述了四氢吡喃基（THP）醚的会聚一步式转化。根据我们之前的实验，已证明三氟甲磺酸铟（III）是将THP醚转化为相应的乙酸盐的有效催化剂。在进一步的深入研究中，我们开发了使用各种酸酐部分的THP醚的有用转化反应。三氟甲磺酸铟（III）被确认为合适的催化剂，收率良好至极佳。描述了这一单步转换的细节。
• Misutsch et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 189,191
  作者：Misutsch et al.

  DOI：——

  日期：——
• (Hetero)aroyl esters of 2-(N-phthalimido)ethanol and analogues: parallel synthesis, anti-HIV-1 activity and cytotoxicity
  作者：Sara Cesarini、Andrea Spallarossa、Angelo Ranise、Silvia Schenone、Paolo La Colla、Gabriella Collu、Giuseppina Sanna、Roberta Loddo

  DOI：10.1007/s00044-009-9192-x

  日期：2010.5

  The structural simplification of the non-nucleoside reverse transcriptase inhibitors (NNRTIs) O-(2-phthalimidoethyl)-N-(hetero)aroyl-N-arylthiocarbamates led us to design (hetero)aroyl esters of 2-(N-phthalimido)ethanol as a potential new class of anti-HIV-1 agents. The setup of a solution-phase parallel synthesis method allowed the rapid preparation of a high number of analogues. In cell-based assays, 20 of 34 esters showed anti-HIV-1 activity ranging from nanomolar to micromolar concentrations. The most potent esters had only a minor effect or were ineffective in enzyme assay against HIV-1 reverse transcriptase. Variations on the O-(2-phthalimidoethyl) moiety led to compounds devoid of antiretroviral activity, but cytotoxic, in particular those bearing the 4-chloro-3-nitrobenzoyl moiety. The most cytotoxic compound displayed a CC50 value of 1.6 mu M.
• A simple procedure for the esterification of alcohols with sodium carboxylate salts using 1-tosylimidazole (TsIm)
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Mohammad Ali Faghihi、Ali Khalafi-Nezhad

  DOI：10.1016/j.tetlet.2007.12.068

  日期：2008.2

  An efficient and selective method for esterification of alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of RCO2Na (R: alkyl and aryl), TsIm, and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DNIF to afford the corresponding esters in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1 degrees > 2 degrees > 3 degrees. (C) 2007 Elsevier Ltd. All rights reserved.
• Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency
  作者：Tanja Stach、Julia Dräger、Peter H. Huy

  DOI：10.1021/acs.orglett.8b01023

  日期：2018.5.18

  A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric

  介绍了一种在立体化学转化下以高催化效率对提供烷基氯化物，溴化物和碘化物的醇进行亲核取代（S N）的实用方法。二乙基环丙烯酮作为一种简单的路易斯碱有机催化剂与苯甲酰氯作为一种试剂的融合，可实现高达100的显着营业额。此外，首次证明了在转化型S N型转化中使用纯乙酰氯作为化学计量的促进剂。。操作上简单明了的协议展现出高水平的立体声选择性和可伸缩性，并且可以容忍各种功能组。