2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)benzoic acid | 56813-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)benzoic acid
• 英文别名: N,N-(1,8-naphthaloyl)-2-aminobenzoic acid；N-(1,8-naphthaloyl)-2-aminobenzoic acid；2-(1,8-naphthalimido)benzoic acid；N-(2-Carboxyphenyl)-naphthalimid；2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzoic acid；2-(1,3-dioxobenzo[de]isoquinolin-2-yl)benzoic acid
• CAS: 56813-55-9
• 化学式: C₁₉H₁₁NO₄
• 分子量: 317.301
• InChiKey: ZUTNAGBPVPAWSD-UHFFFAOYSA-N

物化性质

• 熔点：
  292 °C(Solv: chloroform (67-66-3))
• 沸点：
  590.9±42.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)
• 溶解度：
  >47.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)benzoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 16.0h， 生成 N-(1,8-naphthaloyl)-2-aminobenzoyl chloride
  参考文献：
  名称：

  异吲哚并[2,1- a ]吲哚-6-ones的新方法†

  摘要：

  从合适的2-（N-邻苯二甲酰基）苯甲酸开始，已经开发出一种方便的方法制备异吲哚并[2，1 - a ]吲哚-6-酮。形成酰氯与亚硫酰氯 然后用 亚磷酸三乙酯 在合适的溶剂中进行多步反应，得到四环β-酮膦酸酯，将其还原为 硼氢化钠以良好的总收率获得了所需的吲哚酮。还从N，N-（1,8-萘基）-2-氨基苯甲酸和2-（2,5-二氧代-2,5-二氢-1 H-吡咯-1-基）开始制备类似的β-酮膦酸酯苯甲酸，尽管其中只有萘基产物可被还原硼氢化钠 而不在环系统中裂解酰胺键。

  DOI：

  10.1039/c2ob25314c
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 邻氨基苯甲酸 在 溶剂黄146 作用下， 反应 3.0h， 以82%的产率得到2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)benzoic acid
  参考文献：
  名称：

  吡啶和喹啉对环酰亚胺系链羧酸的溶剂化结构研究

  摘要：

  确定了八种环状酰亚胺束缚羧酸和芳族四羧酸与吡啶（溶剂化物I - VI）和喹啉（VII - VIII）的溶剂化物的结构。在这些溶剂化物中鉴定出不同类型的氢键基序（离散或环状）。溶剂化物I和II具有离散的O-H···N相互作用，溶剂化物III和VIII具有由O-H···N和CHH···O相互作用产生的循环相互作用的组合，溶剂化物IV，V和VII具有上述两种相互作用，即离散和周期性相互作用，而溶剂化VI是一个例外，它具有离散的O·H··N以及R 2 2（8）类型的相互作用，并且为不完全裂解羧酸部分的二聚体组装提供了模型系统。根据各种氢键基序的结果，对由甲酸产生的相似基序及其与吡啶和喹啉的相互作用进行密度泛函理论计算（DFT）。对于吡啶甲酸体系，DFT计算表明，环状R 2 2（7）基序和离散基序之间的能量差为〜0.6 kcal / mol。如此小的差异说明了溶剂合物I - V中两种类型的结构图案的

  DOI：

  10.1021/cg900938x

文献信息

• Helicity Induction in a Bichromophore:  A Sensitive and Practical Chiroptical Method for Absolute Configuration Determination of Aliphatic Alcohols
  作者：Jacek Gawroński、Marcin Kwit、Krystyna Gawrońska

  DOI：10.1021/ol0268079

  日期：2002.11.1

  [reaction: see text] A practical method for the determination of the absolute configuration of aliphatic secondary alcohols, based on the circular dichroism of the readily available N-(1,8-naphthaloyl)-2-aminobenzoyl (NAB) derivative, is presented. The origin of the induced Cotton effects is traced by ab initio calculations to the dominant helicity of the NAB pi-electron system.

  [反应：见正文]基于确定的N-（1,8-萘基）-2-氨基苯甲酰基（NAB）衍生物的圆二色性，提出了一种测定脂族仲醇绝对构型的实用方法。棉花诱导效应的起因可通过从头算来追溯到NABπ电子系统的主要螺旋度。
• Structures of Bifunctional Molecules Containing Two Very Different Supramolecular Synthons: Carboxylic Acid and Strong π···π Stacking 1,8-Naphthalimide Ring
  作者：Daniel L. Reger、Agota Debreczeni、Jacob J. Horger、Mark D. Smith

  DOI：10.1021/cg200636k

  日期：2011.9.7

  A series of molecules containing a carboxylic acid and a 1,8-naphthalimide group joined by different linkers (HLC1 = CH2; HLC2 = CH2CH2; HLC3 CH2CH2CH2; HLophen = ortho-C6H4; HLC4 = para-C6H4; HLala, = S-CHCH3) have been prepared and structurally characterized. The structures of HLC1, HLC3, and HLala are similar, with alternating hydrogen bonding of the carboxylic acids and pi center dot center dot center dot pi stacking interactions of the naphthalimide groups assembling the molecules into parallel chains that are linked into sheets by a second set of pi center dot center dot center dot pi stacking interactions. Hydrogen bonding and pi center dot center dot center dot pi stacking interactions of the naphthalimide groups also assemble HLC2 into chains, but the chains are alternately oriented at nearly right angles causing the interchain pi center dot center dot center dot pi stacking interaction to organize the chains in an open three-dimensional structure. Three of these open structural units interpenetrate forming a unique three-dimensional network. The rigid ortho-arene linker in HLophen directs the orientation of the pi center dot center dot center dot pi stacking interaction of the naphthalimide rings to be at 60 degrees; when combined with the hydrogen bonding interactions helical one-dimensional chains form that pack into a unique rhombohedral architecture. In the structure of HLC4 center dot DMF, each acid group is hydrogen bonded with the dimethylformamide (DMF) molecule; the structure contains one-dimensional ribbons supported only by the pi center dot center dot center dot pi stacking interactions from the 1,8-naphthalimide groups. All six molecules show fluorescence in the 432-449 nm region. Overall these structural studies show that the 1,8-naphthalimide supramolecular synthon is extremely versatile because it can simultaneously enter into multiple noncovalent interactions.
• A superior molecular bichromophore for the determination of absolute configuration of primary amines
  作者：J. Gawroński、J. Grajewski

  DOI：10.1016/j.tetasy.2004.04.003

  日期：2004.5

  Readily available molecular bichromophore, N-(1,8-naphthaloyl)-3-imino-2-naphthoic acid (NAN), is used to derivatize primary amines. NAN-amides show superior sensitivity in the determination of absolute configuration of amines front the sign of the induced exciton Cotton effect. The sign of the Cotton effect is determined by the preferred helicity of the NAN chromophore, which is dependent on the relative size of the substituents at the chiral (RRC)-R-1-C-2*HN carbon atom. (C) 2004 Elsevier Ltd. All rights reserved.
• A Water Soluble Naphthalimide-Based Chemosensor for Fluorescent Detection CN− in Pure Water and Its Application in Practical Samples
  作者：Li Wang、Wen-Ting Li、Wen-Juan Qu、Yan-Qing Fan、Hong Yao、Qi Lin、Tai-Bao Wei、You-Ming Zhang

  DOI：10.21577/0103-5053.20180030

  日期：——

  By rationally introducing aromatic carboxyl functionalized 1,8-naphthalimide, a water soluble fluorescent chemosensor (DA) was successfully synthesized. It could selectively and sensitively detect CN- in pure water via an intramolecular charge transfer to twisted intramolecular charge transfer (ICT-TICT) state change mechanism. The detection limit of the chemosensor DA to CN was 1.38 x 10(-8) mol L-1 which was lower than 1.9 mu mol L-1 (set by the World Health Organization (WHO)). Notably, DA displayed rapid response (about 1 s) for recognizing CN- in pure water. Furthermore, DA could be applied to monitoring CN- in tap water. Meanwhile, we prepared the test strips based on DA, which could rapidly and efficiently detect CN- in water.
• PLAKIDIN V. L.; KOSHELEVA E. S., ZH. ORGAN. XIMII <ZORK-AE>, 1975, 11, HO 7, 1512-1516
  作者：PLAKIDIN V. L.、 KOSHELEVA E. S.

  DOI：——

  日期：——