methyl (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)acetate | 135980-44-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)acetate
• 英文别名: N-[(methoxycarbonyl)methyl]-1,8-naphthalenedicarboximide；N-(methoxycarbonylmethyl)-1,8-naphthalimide；N,N-(naphthalene-1,8-dicarbonyl)-glycine-methyl ester；N,N-(Naphthalin-1,8-dicarbonyl)-glycin-methylester；Methyl 2-(1,3-dioxobenzo[de]isoquinolin-2-yl)acetate
• CAS: 135980-44-8
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: KZJOFXKSSJVGDO-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  448.2±28.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  methyl (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)acetate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 2.0h， 以0.7 g的产率得到阿司他丁
  参考文献：
  名称：

  Solid-phase synthesis of oligomers carrying several chromophore units linked by phosphodiester backbones

  摘要：

  A method for the preparation of oligomers by linking chromophore units is described. Specifically, the synthesis of chromophore units having a protected-hydroxyl group and a phosphoramidite function is described, along with a method to link several units using solid-phase phosphite-triester protocols. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.074
• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)acetate
  参考文献：
  名称：

  Control of Photophysical Properties of 1,8-Naphthalimides by Electron-Withdrawing Substituents Introduced intoN-Alkyl Side Chains

  摘要：

  在二氯甲烷中，发现萘醛亚胺1–7的荧光强度因在N-烷基侧链中引入电子吸引取代基（如OCOMe、CO2Me、Cl和CN）而显著增强。通过使用皮秒单光子计数法测量荧光生命周期τf，并通过时间分辨热透镜法测定的跨跃量子产率Φisc，确定了1–7在二氯甲烷和乙腈中的荧光发射速率常数kf、系间交叉速率常数kisc和内部转换速率常数kic。这些结果表明，kisc的值随着取代基电子吸引能力的增加而减小。此外，在二氯甲烷中kisc的对数与取代基常数σI（通过σ键的诱导效应）之间几乎呈线性Hammett关系（ρ = −1.48），在乙腈中为ρ = −1.85。因此，电子吸引取代基所引起的荧光强度增强可被解释为从1(ππ*)到3(nπ*)的系间交叉效率降低，后者的能量因取代基通过σ键的诱导效应而增加。

  DOI：

  10.1246/bcsj.20100276

文献信息

• Efficient Cesium Carbonate Promoted N-Alkylations of Aromatic Cyclic Imides Under Microwave Irradiation
  作者：María Blanco、Mercedes Escudero、Lautaro Kremenchuzky、Isabel Perillo、Hugo Cerecetto

  DOI：10.1055/s-0030-1258398

  日期：2011.2

  We present here an efficient and simple method for the N-alkylation of aromatic cyclic imides employing cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70 ˚C). The employment of microwave irradiation presents noteworthy advantages over conventional heating. The method is compatible with base labile functional groups.

  本文介绍了一种高效且简便的方法，通过在低温（20-70℃）无水N,N-二甲基甲酰胺中使用碳酸铯作为碱，来实现芳香环亚胺的N-烷基化。相较于传统加热，采用微波辐射具有显著的优势。该方法与对碱敏感的官能团兼容。
• Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene
  作者：Attila Takács、Péter Ács、László Kollár

  DOI：10.1016/j.tet.2007.10.026

  日期：2008.2

  amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the

  在由乙酸钯（II）和三苯膦原位形成的钯（0）配合物存在下，将1,8-二碘萘与各种伯胺和仲胺进行氨基羰基化反应。在伯胺的情况下，取决于胺与底物的比例，已经在高度化学选择性反应中获得了两种类型的产物：分别以高和低胺与底物的比例形成了二甲酰胺和N-取代的酰亚胺。该反应容许酯官能度，使得氨基酸酯可以用作N-亲核试剂，并且以此方式，可以合成在N-取代基中具有立体异构中心的萘二甲酰亚胺。
• Über die Darstellung von Naphthoylen-imidazolinen
  作者：Hans Eduard Fierz-David、Carlo Rossi

  DOI：10.1002/hlca.193802101182

  日期：——
• Solid-phase synthesis of oligomers carrying several chromophore units linked by phosphodiester backbones
  作者：Anna Aviñó、Isabel Navarro、Josep Farrera-Sinfreu、Miriam Royo、Juan Aymamí、Antonio Delgado、Amadeu Llebaria、Fernando Albericio、Ramon Eritja

  DOI：10.1016/j.bmcl.2008.02.074

  日期：2008.4

  A method for the preparation of oligomers by linking chromophore units is described. Specifically, the synthesis of chromophore units having a protected-hydroxyl group and a phosphoramidite function is described, along with a method to link several units using solid-phase phosphite-triester protocols. (C) 2008 Elsevier Ltd. All rights reserved.
• Control of Photophysical Properties of 1,8-Naphthalimides by Electron-Withdrawing Substituents Introduced into<i>N</i>-Alkyl Side Chains
  作者：Kazuhiko Matsubayashi、Chisato Kajimura、Yasuo Kubo、Toshitada Yoshihara、Seiji Tobita

  DOI：10.1246/bcsj.20100276

  日期：2011.5.15

  The fluorescence intensity of naphthalimides 1–7 in dichloromethane was found to be remarkably enhanced by the introduction of an electron-withdrawing substituent, such as OCOMe, CO2Me, Cl, and CN, into the N-alkyl side chain. The rate constants of the fluorescence emission kf, the intersystem crossing kisc, and the internal conversion kic for 1–7 in dichloromethane and in acetonitrile were determined based on the measurements of the fluorescence lifetimes τf, by using picosecond single photon counting, and the quantum yields of the intersystem crossing Φisc determined by time-resolved thermal lensing. These results indicate that the value of kisc decreases with an increase in the electron-withdrawing ability of the substituent. Furthermore, an almost linear Hammett relationship (ρ = −1.48 in dichloromethane, ρ = −1.85 in acetonitrile) between the logarithm of kisc and the substituent constant σI for inductive effect of the substituent through the σ bond was observed. The enhancement of the fluorescence intensity by the introduction of electron-withdrawing substituents was thus explained by a decrease in the efficiency of the intersystem crossing from 1(ππ*) to 3(nπ*), whose energy was increased by the inductive effect of the substituent through the σ bonds.

  在二氯甲烷中，发现萘醛亚胺1–7的荧光强度因在N-烷基侧链中引入电子吸引取代基（如OCOMe、CO2Me、Cl和CN）而显著增强。通过使用皮秒单光子计数法测量荧光生命周期τf，并通过时间分辨热透镜法测定的跨跃量子产率Φisc，确定了1–7在二氯甲烷和乙腈中的荧光发射速率常数kf、系间交叉速率常数kisc和内部转换速率常数kic。这些结果表明，kisc的值随着取代基电子吸引能力的增加而减小。此外，在二氯甲烷中kisc的对数与取代基常数σI（通过σ键的诱导效应）之间几乎呈线性Hammett关系（ρ = −1.48），在乙腈中为ρ = −1.85。因此，电子吸引取代基所引起的荧光强度增强可被解释为从1(ππ*)到3(nπ*)的系间交叉效率降低，后者的能量因取代基通过σ键的诱导效应而增加。