2-甲基-1H-苯并(去)异喹啉-1,3(2H)-二酮 | 2382-08-3

• 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
• 中文名称: 2-甲基-1H-苯并(去)异喹啉-1,3(2H)-二酮
• 英文名称: N-methylnaphthalimide
• 英文别名: N-methyl-1,8-naphthalimide；2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione；N-methyl-1,8-naphthalenedicarboximide；N-Methylnaphthalimid；2-methylbenzo[de]isoquinoline-1,3-dione
• CAS: 2382-08-3
• 化学式: C₁₃H₉NO₂
• mdl: MFCD00179004
• 分子量: 211.22
• InChiKey: CZMAEVKITVSOPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-甲基-1H-苯并(去)异喹啉-1,3(2H)-二酮 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以94%的产率得到2-methyl-2,3-dihydro-benzo[de]isoquinolin-1-one
  参考文献：
  名称：

  New and Convenient Synthesis of 2-Substituted 2,3-Dihydro-1H-benz[de]isoquinolin-1-ones

  摘要：

  通过在室温下使用钠或锌氢化硼对2-取代的1H-benz[de]isoquinoline-1,3(2H)-二酮进行化学选择性还原，获得了多种2-取代的2,3-二氢-1H-benz[de]isoquinolin-1-酮，产率很高。

  DOI：

  10.1246/bcsj.61.2238
• 作为产物：
  描述：

  N-<(trimethylsilyl)methyl>-1,8-naphthalimide 以 甲醇 为溶剂， 反应 4.5h， 以75%的产率得到2-甲基-1H-苯并(去)异喹啉-1,3(2H)-二酮
  参考文献：
  名称：

  Novel and Efficient Azomethine Ylide Forming Photoreactions of N-(Silylmethyl)phthalimides and Related Acid and Alcohol Derivatives

  摘要：

  An investigation of the photochemistry of N-(silylmethyl)phthalimides and related alpha-phthaloylacetic acids and 2-phenylethanol derivatives has uncovered new excited state processes resulting in the formation of azomethine ylide intermediates. Irradiation of N-[(trimethylsilyl)methyl]phthalimide in MeCN promotes C to O silyl transfer to generate the corresponding azomethine ylide which is efficiently trapped by reaction with water to yield the N-methylphthalimide or by dipolar cycloaddition with acetone, methyl acrylate, or acrylonitrile. Cycloadditions with the latter two dipolarophiles are both regioselective and endo-stereoselective. These processes can be triplet photosensitized by use of acetophenone. The related N-[(trimethylsilyl)methyl]-1,8-naphthalimide reacts in a similar manner upon irradiation in MeCN solutions containing the dipolarophiles methyl acrylate and acrylonitrile to produce cycloadducts which undergo spontaneous elimination of TMSOH, yielding alpha,beta-unsaturated ester or nitrile products. The ylide formed by irradiation of the (silylmethyl)phthalimide is trapped in a stereospecific (retention) manner by the dipolarophiles trans-hex-4-en-3-one, dimethyl maleate, and dimethyl fumarate. The effect of aryl ring substitution on the regiochemical course of the photoinduced C to O silyl migration process was probed by use of the 4-methoxy- and 4-carbomethoxyl-N-(silylmethyl)phthalimides. Irradiation of the former substance in an MeCN solution containing acrylonitrile gives rise to a single adduct whose structure suggests that silyl migration to oxygen of the carbonyl meta to the OMe substituent is highly favored. In contrast, the 4-carbomethoxyphthalimide is converted under these conditions to a mixture of regioisomeric adducts. Thus, silyl migration in the excited state of this substance is nonselective. In accord with hints found in earlier observations made by Kanaoka (Chem. Pharm. Bull. 1982, 30, 1263), N-phthalimide derivatives of the alpha-amino acids glycine, alanine, and phenylalanine undergo similar ylide forming photoreactions upon irradiation in MeCN solutions. The azomethine ylides produced by photodecarboxylation of these substances are efficiently trapped by dipolarophiles, and the overall photoreactions starting with the alanine and phenylalanine derivatives are highly stereoselective. Finally, the N-phthalimide derivative of 2-amino-1-phenylethanol also is transformed to a related ylide upon irradiation in MeCN. The nature, regiochemical and stereochemical course, and mechanistic interpretation of these new azomethine ylide forming photoreactions are discussed in this publication.

  DOI：

  10.1021/ja00115a004

文献信息

• New strategy for the azido–ascorbic acid reaction: a convenient chemosensor and its imaging in garlic slice tissues
  作者：Dan Zhang、Na Li、Yiming Ma、Ruixue Wang、Jinyi Wang、Junru Wang

  DOI：10.1039/c8nj00589c

  日期：——

  Ascorbic acid (AA) is a vital nutritional factor in many fruits and plants, and abnormal levels of AA are closely associated with several diseases. Therefore, the development of convenient methods for monitoring AA levels in biological systems is of great importance. In this work, we designed and synthesized three chemosensors for the rapid turn-on detection of AA via a new strategy for the azido–ascorbic

  抗坏血酸（AA）是许多水果和植物中至关重要的营养因子，AA含量异常与多种疾病密切相关。因此，开发用于监测生物系统中AA水平的便利方法非常重要。在这项工作中，我们设计并合成了三种化学传感器，用于通过叠氮-抗坏血酸反应的新策略快速启动AA的检测。的化学传感器是基于在不同的位点（探针叠氮基-1,8-萘二甲酰亚胺部分1，2，和3）。实验结果表明，探针2表现出对AA的高选择性，检测极限为74 nM。它的还原比带有3-取代叠氮化物基团的探针3的还原更容易。此外，探针2首次成功用于大蒜切片组织中AA的成像。
• HIGHLY-FLUORESCENT AND PHOTO-STABLE CHROMOPHORES FOR ENHANCED SOLAR HARVESTING EFFICIENCY
  申请人：NITTO DENKO CORPORATION

  公开号：US20130074927A1

  公开（公告）日：2013-03-28

  The invention provides highly fluorescent materials comprising a single (n=0) or a series (n=1, 2, etc.) of benzo heterocyclic systems. The photo-stable highly luminescent chromophores are useful in various applications, including in wavelength conversion films. Wavelength conversion films have the potential to significantly enhance the solar harvesting efficiency of photovoltaic or solar cell devices.

  这项发明提供了包括单个（n=0）或一系列（n=1、2等）苯并杂环系统的高荧光材料。这种光稳定的高发光色团在各种应用中很有用，包括波长转换膜。波长转换膜有潜力显著提高光伏或太阳能电池器件的太阳能收集效率。
• Resist lower-layer composition containing thermal acid generator, resist lower layer film-formed substrate, and patterning process
  申请人：Ohsawa Youichi

  公开号：US20100119970A1

  公开（公告）日：2010-05-13

  There is disclosed a resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film, wherein the resist lower-layer composition becomes insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and wherein the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid represented by the general formula (1) by heating at a temperature of 100° C. or higher. RCOO—CH 2 CF 2 SO 3 − H + (1) There can be provided a resist lower-layer composition in a multi-layer resist method (particularly, a two-layer resist method and a three-layer resist method), which composition is used to form a layer lower than a photoresist layer acting as a resist upper layer film, which composition becomes insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and which composition is capable of forming a resist lower layer film, intermediate-layered film, and the like having a higher anti-poisoning effect and exhibiting a lower load to the environment.

  揭示了一种抗性下层组合物，配置为在光刻中使用的多层抗性方法中使用，用于形成低于作为抗性上层膜的光刻胶层的一层，其中抗性下层组合物在形成下层后变得不溶解或难溶解于碱性显影剂中，且抗性下层组合物至少包括用于通过在100°C或更高温度下加热生成由通式（1）表示的酸的热酸发生剂。 可以提供一种抗性下层组合物，用于多层抗性方法（特别是双层抗性方法和三层抗性方法），该组合物用于形成低于作为抗性上层膜的光刻胶层的一层，该组合物在形成下层后变得不溶解或难溶解于碱性显影剂中，并且该组合物能够形成具有更高抗毒性效果并表现出对环境负荷较低的抗性下层膜、中间层膜等。
• NOVEL PHOTOACID GENERATOR, RESIST COMPOSITION, AND PATTERNING PROCESS
  申请人：Ohsawa Youichi

  公开号：US20090246694A1

  公开（公告）日：2009-10-01

  Photoacid generators generate sulfonic acids of formula ( 1 a) upon exposure to high-energy radiation. ROC(═O)R 1 —COOCH 2 CF 2 SO 3 − H + (1a) RO is OH or C 1 -C 20 organoxy, R 1 is a divalent C 1 -C 20 aliphatic group or forms a cyclic structure with RO. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

  光酸发生剂在高能辐射作用下生成式（1a）的磺酸。 ROC(═O)R1—COOCH2CF2SO3−H+(1a) RO为OH或C1-C20有机氧基，R1为二价的C1-C20脂肪族基团或与RO形成环状结构。这些光酸发生剂与树脂相容，可以控制酸的扩散，因此适用于化学增感抗蚀组合物的使用。
• [EN] ORIGINAL DRUG MOLECULES FOR THE TREATMENT OF PARASITIC AND NEOPLASTIC DISEASES AND METHODS FOR PREPARATION THEREOF<br/>[FR] MOLÉCULES DE MÉDICAMENT ORIGINALES POUR LE TRAITEMENT DE MALADIES PARASITAIRES ET NÉOPLASIQUES ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：T C MEDIPOL UENIVERSITESI

  公开号：WO2018106200A1

  公开（公告）日：2018-06-14

  The present invention relates to a novel drug molecules formula (I), a novel method for use in preparation of said drug molecules and use of said drug molecules for preparation of a pharmaceutical composition for use in treatment of viral, bacterial and neoplastic diseases.

  本发明涉及一种新型药物分子的化学式（I），一种用于制备该药物分子的新方法，以及利用该药物分子制备用于治疗病毒、细菌和肿瘤疾病的药物组合物的用途。