6-chloro-2,3-naphthalenedicarboxylic anhydride | 59883-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 6-chloro-2,3-naphthalenedicarboxylic anhydride
• 英文别名: 6-chloronaphtho[2,3-c]furan-1,3-dione；6-chloro-2,3-naphthalic anhydride；6-chlorobenzo[f][2]benzofuran-1,3-dione
• CAS: 59883-29-3
• 化学式: C₁₂H₅ClO₃
• 分子量: 232.623
• InChiKey: CFJXZNREFFTFFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2,3-naphthalenedicarboxylic anhydride 在 尿素 作用下， 反应 2.0h， 以95%的产率得到6-chloro-1H-benzo[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide

  摘要：

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.002
• 作为产物：
  描述：

  6-chloro-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3-c]furan-1,3-dione 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 6-chloro-2,3-naphthalenedicarboxylic anhydride
  参考文献：
  名称：

  Dual Fluorescent N-Aryl-2,3- naphthalimides: Applications in Ratiometric DNA Detection and White Organic Light-Emitting Devices

  摘要：

  A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.

  DOI：

  10.1021/ol101760m

文献信息

• Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative
  作者：Alan R. Katritzky、Sevil Ozcan、Ekaterina Todadze

  DOI：10.1039/c000684j

  日期：——

  Convenient and efficient synthesis of a new environmentally sensitive chlorine-substituted 2,3-naphthalimide-based fluorophore is reported. Benzotriazole carboxyl group activation of the 6-chloro-fluorophore enabled quick labeling of free and Fmoc-protected amino acids. The photophysical properties of the compounds obtained include high quantum yields in solvents of different polarity: water, methanol, acetonitrile and hexane.

  报道了一种新型环境敏感型氯代2,3-萘酞亚胺基荧光团的高效便捷合成方法。通过苯并三唑羧基活化6-氯荧光团，可实现对游离氨基酸和Fmoc保护氨基酸的快速标记。所获得化合物的光物理性质包括在不同极性溶剂（水、甲醇、乙腈和己烷）中具有高量子产率。
• Design, Synthesis and Discovery of 1-(2-(6-Chloro-3-methylsulfonyl)-naphthyl)-1H-pyrazole-5-carboxylamides as Highly Potent Factor Xa Inhibitors
  作者：Zhaozhong Jon Jia、Robert Murry Scarborough、Penglie Zhang、Sherin Halfon、Ann Elizabeth Arfsten、Uma Sinha、Bing-Yan Zhu

  DOI：10.1248/cpb.57.1004

  日期：——

  Based upon the biphenyl 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides reported in our previous communications, we designed and discovered 2-(6-chloro-3-methylsulfonyl)-naphthyl as an optimal factor Xa S1 binding element. Employing a key Diels–Alder reaction of 1,4-dihydro-2,3-benzoxathiin-3-oxide with maleic anhydride and a key Cu(I)-mediated methylsulfonylation, we prepared two biphenyl 1-(2-(6-chloro-3-methylsulfonyl)-naphthyl)-1H-pyrazole-5-carboxylamides as highly potent factor Xa inhibitors with Ki values of 0.065 nM and 0.045 nM respectively, and demonstrated the synergistically enhanced binding interaction in the factor Xa S1 site.

  基于我们之前的通讯报道的双苯并[b,f][1,4]氧氮杂卓-1-(2-萘基)-1H-吡唑-5-羧酰胺类化合物，我们设计并发现了2-(6-氯-3-甲磺酰基)萘基作为优选的因子Xa S1结合元件。通过使用1,4-二氢-2,3-苯并噻嗪-3-氧化物与马来酸酐的关键Diels-Alder反应和关键的Cu(I)介导的甲磺酰化反应，我们制备了两种双苯并[b,f][1,4]氧氮杂卓-1-(2-(6-氯-3-甲磺酰基)萘基)-1H-吡唑-5-羧酰胺，它们作为高效的因子Xa抑制剂，其Ki值分别为0.065 nM和0.045 nM，并展示了在因子Xa S1位点协同增强的结合相互作用。
• Analgesic basic naphthalene derivatives
  申请人：Glaxo Laboratories Limited

  公开号：US04062955A1

  公开（公告）日：1977-12-13

  Compounds of the general formula: ##STR1## wherein the groups CHR.sup.1 NR.sup.2 R.sup.3 and CHR.sup.4 NR.sup.5 R.sup.6 may be the same or different and where the group CHR.sup.4 NR.sup.5 R.sup.6 is in either the 1 or the 3 position and R.sup.1 and R.sup.4 independently represent a hydrogen atom or an aryl group; R.sup.2, r.sup.3, r.sup.5 and R.sup.6 which may be the same or different are each a hydrogen atom or an alkyl group or an aryl group both of which may in turn be substituted by one or more hydroxy, alkoxy, acyloxy, dialkylamino or aryl groups or the groups --NR.sup.2 R.sup.3 and/or NR.sup.5 R.sup.6 represent a heterocyclic ring containing one or more hetero atoms and which ring may optionally be substituted by an alkyl, aryl or aralkyl group and in which either aromatic ring of the naphthalene nucleus may be further substituted; with the proviso that when R.sup.1, R.sup.4, R.sup.2 and R.sup.5 are hydrogen, then R.sup.3 and R.sup.6 cannot both be benzyl, when the second substituent is in the 1 position; and when R.sup.1 and R.sup.4 are hydrogen, then R.sup.2, R.sup.3, R.sup.5 and R.sup.6 cannot all be methyl when the second substituent is in the 1 position; and when R.sup.1 and R.sup.4 are hydrogen, then R.sup.2 and R.sup.3 and R.sup.5 and R.sup.6 together with the nitrogen atom cannot both be piperidino when the second substituent is in the 3 position and the naphthalene nucleus is further substituted by hydroxy in the 1 and 4 positions; and pharmaceutically acceptable salts of such compounds; and hydrates of such compounds and such salts. The compounds have activity on the central nervous system in particular as analgesics.

  通式为##STR1##的化合物，其中组CHR.sup.1 NR.sup.2 R.sup.3和CHR.sup.4 NR.sup.5 R.sup.6可以相同或不同，且组CHR.sup.4 NR.sup.5 R.sup.6在1或3位，R.sup.1和R.sup.4分别表示氢原子或芳基基团；R.sup.2、R.sup.3、R.sup.5和R.sup.6可以相同或不同，分别表示氢原子、烷基或芳基基团，它们又可以被一个或多个羟基、烷氧基、酰氧基、二烷基氨基或芳基基团取代，或者组--NR.sup.2 R.sup.3和/或NR.sup.5 R.sup.6表示含有一个或多个杂原子的杂环，该环可以选择性地被烷基、芳基或芳基烷基取代，且萘环的任一芳香环可以进一步取代；但是当R.sup.1、R.sup.4、R.sup.2和R.sup.5为氢时，当第二取代基位于1位时，R.sup.3和R.sup.6不能同时为苄基；当R.sup.1和R.sup.4为氢时，当第二取代基位于1位时，R.sup.2、R.sup.3、R.sup.5和R.sup.6不能同时为甲基；当R.sup.1和R.sup.4为氢时，当第二取代基位于3位且萘环在1和4位进一步取代为羟基时，R.sup.2和R.sup.3和R.sup.5和R.sup.6连同氮原子不能同时为哌啶基；以及这些化合物的药学上可接受的盐和这些化合物和这些盐的水合物。这些化合物在中枢神经系统中具有活性，特别是作为镇痛剂。
• Dual Fluorescent <i>N</i>-Aryl-2,3- naphthalimides: Applications in Ratiometric DNA Detection and White Organic Light-Emitting Devices
  作者：Premchendar Nandhikonda、Michael D. Heagy

  DOI：10.1021/ol101760m

  日期：2010.11.5

  A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.
• Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide
  作者：Kishore Baathulaa、Yufang Xu、Xuhong Qian

  DOI：10.1016/j.jphotochem.2010.09.002

  日期：2010.11

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved