2-(蒽-9-基甲基)异吲哚-1,3-二酮 | 94617-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2-(蒽-9-基甲基)异吲哚-1,3-二酮
• 英文名称: N-(9-anthranylmethyl)phthalimide
• 英文别名: 9-phthalimidomethylanthracene；1H-Isoindole-1,3(2H)-dione, 2-(9-anthracenylmethyl)-；2-(anthracen-9-ylmethyl)isoindole-1,3-dione
• CAS: 94617-21-7
• 化学式: C₂₃H₁₅NO₂
• 分子量: 337.378
• InChiKey: VXAHLCUBDORWST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  2-(蒽-9-基甲基)异吲哚-1,3-二酮 在 zinc diacetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  喹喔啉壁π堆积分子：合成，构象和发光性质

  摘要：

  一系列半刚性的N-苯基琥珀酰亚胺I（11Xy），N-芳基甲基琥珀酰亚胺II（18Xy）和N，N '-（1,4-亚芳基双（亚甲基））二琥珀酰亚胺III（19XyX合成了以喹喔啉（QX）为壁的二甲基喹喔啉（diMQX）或苯并喹喔啉（BQX）环。通过核磁共振和荧光光谱分别以相互各向异性屏蔽和激基复合物形成来检测溶液中的分子内π-π相互作用。X射线晶体学分析揭示了固态的优先构象，这与通过NMR和荧光光谱进行构象研究的结果相符。结果共同表明18Xy和19XyX 由分子内π-π相互作用以π堆积（面对面）或T形（边缘面对面）构型驱动，分别优先采用折叠和双折叠构型，其中间隔开的芳环彼此紧密地取向。

  DOI：

  10.1016/j.tet.2014.08.071
• 作为产物：
  描述：

  9-氯甲基蒽 、 potassium phtalimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(蒽-9-基甲基)异吲哚-1,3-二酮
  参考文献：
  名称：

  Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

  摘要：

  预期存在前组织效应，设计并合成了三脚架型阴离子主体分子。研究表明，两种新型硫脲衍生物，其六取代苯环作为前组织间隔基，能有效识别四面体磷酸二氢根离子。具有吡啶并环部分与硫脲结合位点相邻的三脚架型氟光受体1在加入客体阴离子后，在乙腈中表现出长波长发射。另一方面，通过亚甲基单元与蒽基团相连的三脚架型硫脲受体2在加入阴离子后荧光强度降低。在这两种情况下，发射强度的变化程度依次为H2PO4^- > CH3COO^- > Cl^- ≫ ClO4^-，这与仅有一个结合位点的参考化合物明显不同。这些三脚架型氟光受体的结合常数（Ka）也证实了在该均相溶液系统中对磷酸二氢根离子相对于更基础的醋酸根离子的选择性。利用前组织效应的氟光受体特征显示出有望开发具有特定阴离子选择性的化学离子传感器。

  DOI：

  10.1039/b105913k

文献信息

• Deamination of 1-Alkyl-9-aminomethyltriptycenes. Participation of a Neighboring 1-Alkyl Substituent
  作者：Gaku Yamamoto、Ai Koseki、Jun Sugita、Hisashi Mochida、Mao Minoura

  DOI：10.1246/bcsj.79.1585

  日期：2006.10

  N 2 from a primary alkanediazonium ion predominantly takes place concomitantly with participation of a C-H bond of the neighboring 1-alkyl group to form a nonclassical cationic species with a three-center two-electron bonding, while the loss of N 2 from a secondary alkanediazonium ion occurs spontaneously to form a secondary carbocation. Solvent effects (CHCl 3 vs AcOH) are explained in terms of lower

  在 CHCl3 和 AcOH 中进行 l-烷基-9-氨基甲基三烯（烷基 = Me、Et、i-Pr 和 t-Bu）和 9-（1-氨基乙基）-1-甲基三烯的脱氨基反应，产物分布为学习了。结果表明，从初级烷烃重氮离子中失去 N 2 主要伴随着相邻 1-烷基的 CH 键的参与而发生，以形成具有三中心双电子键的非经典阳离子物种，而失去N 2 来自二级烷烃重氮离子自发地形成二级碳正离子。由于溶剂化作用，溶剂效应（CHCl 3 与 AcOH）的解释是 AcO 在 AcOH 中的亲核性/碱度比在 CHCl 3 中低。
• 10.1039/d4ob00576g
  作者：Ryoo, Jeong Yup、Han, Min Su

  DOI：10.1039/d4ob00576g

  日期：——

  evaluation of various amidation catalysts. Using this approach, boronic acids were evaluated for their catalytic potential. Our findings reveal that 2-hydroxyphenylboronic acid (C7), previously deemed inefficient for aliphatic acids, effectively catalyzes the amidation of aromatic acids. The catalysts identified through this method consistently achieved high yields, reaching up to 98% across a broad spectrum

  羧酸与胺的直接酰胺化具有重要意义；因此，涉及硼酸的催化过程得到了广泛的研究。然而，针对芳香族羧酸酰胺化的研究仍然有限。在这项研究中，我们引入了一种采用蒽衍生物探针的基于荧光的筛选方法，有助于快速评估各种酰胺化催化剂。使用这种方法，评估了硼酸的催化潜力。我们的研究结果表明，以前被认为对脂肪酸无效的 2-羟基苯基硼酸 (C7) 可有效催化芳香酸的酰胺化。通过该方法鉴定的催化剂始终实现高产率，在多种底物中均达到 98%。
• Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range
  作者：Elisabetta Teodori、Silvia Dei、Patricia Quidu、Roberta Budriesi、Alberto Chiarini、Arlette Garnier-Suillerot、Fulvio Gualtieri、Dina Manetti、Maria Novella Romanelli、Serena Scapecchi

  DOI：10.1021/jm980440p

  日期：1999.5.1

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.
• Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing
  作者：Shin-ichi Sasaki、Daniel Citterio、Satoru Ozawa、Koji Suzuki

  DOI：10.1039/b105913k

  日期：2001.11.29

  Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4− > CH3COO− > Cl− ≫ ClO4−, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.

  预期存在前组织效应，设计并合成了三脚架型阴离子主体分子。研究表明，两种新型硫脲衍生物，其六取代苯环作为前组织间隔基，能有效识别四面体磷酸二氢根离子。具有吡啶并环部分与硫脲结合位点相邻的三脚架型氟光受体1在加入客体阴离子后，在乙腈中表现出长波长发射。另一方面，通过亚甲基单元与蒽基团相连的三脚架型硫脲受体2在加入阴离子后荧光强度降低。在这两种情况下，发射强度的变化程度依次为H2PO4^- > CH3COO^- > Cl^- ≫ ClO4^-，这与仅有一个结合位点的参考化合物明显不同。这些三脚架型氟光受体的结合常数（Ka）也证实了在该均相溶液系统中对磷酸二氢根离子相对于更基础的醋酸根离子的选择性。利用前组织效应的氟光受体特征显示出有望开发具有特定阴离子选择性的化学离子传感器。
• Quinoxaline-walled π-stacking molecules: synthesis, conformation, and luminescence properties
  作者：Teh-Chang Chou、Jing-Kai Huang、Sushilkumar S. Bahekar、Ju-Hsiou Liao

  DOI：10.1016/j.tet.2014.08.071

  日期：2014.11

  synthesized. Intramolecular π–π interactions in solution were detected by NMR and fluorescence spectroscopy, in terms of reciprocal anisotropic shielding and exciplex formation, respectively. The X-ray crystallographic analysis revealed the preferential conformations in solid state, which were compatible with the results of conformational studies by NMR and fluorescence spectroscopy. The results collectively

  一系列半刚性的N-苯基琥珀酰亚胺I（11Xy），N-芳基甲基琥珀酰亚胺II（18Xy）和N，N '-（1,4-亚芳基双（亚甲基））二琥珀酰亚胺III（19XyX合成了以喹喔啉（QX）为壁的二甲基喹喔啉（diMQX）或苯并喹喔啉（BQX）环。通过核磁共振和荧光光谱分别以相互各向异性屏蔽和激基复合物形成来检测溶液中的分子内π-π相互作用。X射线晶体学分析揭示了固态的优先构象，这与通过NMR和荧光光谱进行构象研究的结果相符。结果共同表明18Xy和19XyX 由分子内π-π相互作用以π堆积（面对面）或T形（边缘面对面）构型驱动，分别优先采用折叠和双折叠构型，其中间隔开的芳环彼此紧密地取向。