5,6-dichloro-3-iminoisoindolin-1-one | 35190-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5,6-dichloro-3-iminoisoindolin-1-one
• 英文别名: 5,6-dichloro-3-imino-2H-isoindol-1-one；5,6-dichloro-3-iminoisoindol-1-one
• CAS: 35190-38-6
• 化学式: C₈H₄Cl₂N₂O
• mdl: MFCD24552845
• 分子量: 215.039
• InChiKey: NOFJASWEFDKODU-UHFFFAOYSA-N

物化性质

• 熔点：
  330-335 °C (decomp)
• 沸点：
  428.5±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-dichloro-3-iminoisoindolin-1-one 在 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 Ethyl 2-cyano-2-(5,6-dichloro-1-cyano-3-oxo-2-propylisoindol-1-yl)acetate
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  2-cyano-4,5-dichlorobenzoic acid methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 5,6-dichloro-3-iminoisoindolin-1-one
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016

文献信息

• Copper-mediated imine–nitrile coupling leading to unsymmetric 1,3,5-triazapentadienato complexes containing the incorporated iminoisoindolin-1-one moiety
  作者：Maximilian N. Kopylovich、Konstantin V. Luzyanin、Matti Haukka、Armando J. L. Pombeiro、Vadim Yu. Kukushkin

  DOI：10.1039/b805243c

  日期：——

  The copper(II)-mediated integration between various 3-iminoisoindolin-1-ones and neat organonitriles (which play a dual role of solvent and reactant), under heating for ca. 12 h, and without requiring any base, accomplishes the release of the solid (1,3,5-triazapentadienato)CuII complexes [CuHN=C(R)NC(C6R1R2R3R4CO)N}2] (1–11) bearing the incorporated iminoisoindolin-1-one fragment. These compounds were isolated in moderate to good yields (44–78%) and do not require further purification. The iminoisoindolinone–nitrile coupling is CuII-mediated and has a general character insofar as it can be efficiently applied for both unsubstituted (R1–R4 = H) and substituted iminoisoindolin-1-ones (R1, R3, R4 = H, R2 = Me; R1, R4 = H, R2, R3 = Cl; R1–R4 = F), and a wide range of nitriles (R = Me, Et, Prn, Pri, C6H11, CH2Ph). Complexes 1–11 were characterized by elemental analyses (C, H, N), FAB+-MS, IR spectroscopy, and additionally compounds 1, 2 and 4 by single-crystal X-ray diffraction.

  铜（II）介导的各种 3-亚氨基异吲哚啉-1-酮与纯有机腈类化合物（起着溶剂和反应物的双重作用）之间的结合，在加热约 12 小时的情况下，不需要任何碱，就能释放出固体（1,3,5-三氮杂戊二烯）CuII 复合物[CuHN=C(R)NC(C6)]。在加热约 12 小时后，不需要任何碱，就能释放出含有掺入的亚氨基异吲哚啉-1-酮片段的固体（1,3,5-三氮杂戊二烯）CuII 复合物[CuHN=C(R)NC(C6R1R2R3R4CO)N}2] (1â11)。这些化合物以中等至良好的收率（44%-78%）分离出来，无需进一步纯化。亚氨基异吲哚啉酮与腈的偶联反应是由 CuII 介导的，具有通用性，可以有效地应用于未取代的（R1âR4 = H）和取代的亚氨基异吲哚啉-1-酮（R1, R3, R4 = H, R2 = Me；R1, R4 = H, R2, R3 = Cl；R1âR4 = F）以及多种腈类（R = Me, Et, Prn, Pri, C6H11, CH2Ph）。络合物 1â11 通过元素分析（C、H、N）、FAB+-MS 和红外光谱进行表征，化合物 1、2 和 4 则通过单晶 X 射线衍射进行表征。
• Novel and Mild Route to Phthalocyanines and 3‐Iminoisoindolin‐1‐ones <i>via N</i> , <i>N</i> ‐Diethylhydroxylamine‐Promoted Conversion of Phthalonitriles and a Dramatic Solvent‐Dependence of the Reaction
  作者：Konstantin V. Luzyanin、Vadim Yu. Kukushkin、Maximilian N. Kopylovich、Alexey A. Nazarov、Mathea Sophia Galanski、Armando J. L. Pombeiro

  DOI：10.1002/adsc.200700261

  日期：2008.1.4

  phthalonitriles 1, 2, or 4 (R1, R3, R4=H, R2=NO2) (4 equivs.) with Et2NOH (8 equivs.) in the presence of a metal salt MCl2 (M=Zn, Cd, Co, Ni) (1 equiv.) in n-BuOH or without solvent results in the formation of metallated phthalocyanine species (9–17). Upon refluxing in freshly distilled dry chloroform, phthalonitrile 1 or its substituted analogues 2, 3 or 5 (R1–R4=F) (1 equiv.) react with N,N-diethylhydroxylamine

  将邻苯二甲腈C 6 R 1 R 2 R 3 R 4（CN）2 1（R 1 -R 4 = H）或其取代的衍生物2（R 1，R 3，R 4 = H，R 2 = Me）或3（R 1，R 4 = H，R 2，R 3 = Cl）（1当量）和N，N-二乙基羟胺，Et 2 NOH（4当量）在甲醇中放置4 h（路线A）沉淀出对称的（6和8）和非对称的（7）酞菁异构体混合物，分离出的产率很高（55–65％）。邻苯二甲腈的反应1，2，或4（R 1，R 3，R 4 = H，R 2 = NO 2）（4所做的工作就是。）用Et 2 NOH在金属盐的MC1的存在（8所做的工作就是。）2（M = Zn，Cd，Co，Ni）（1当量）在n- BuOH中或在没有溶剂的情况下会形成金属化的酞菁类物质（9 – 17）。当在新蒸馏的干燥的回流氯仿，邻苯二甲腈1或其取代的类似物2，3或5（R 1 -R 4 = F）（1个当量）与反应Ñ，Ñ
• Coupling between 3-Iminoisoindolin-1-ones and Complexed Isonitriles as a Metal-Mediated Route to a Novel Type of Palladium and Platinum Iminocarbene Species
  作者：Konstantin V. Luzyanin、Armando J. L. Pombeiro、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1021/om800517c

  日期：2008.10.27

  including the monoadduct [PtClC(N═C(C6H4CON))═N(H)C6H4OMe-4}(C≡NC6H4OMe-4)] (29), the unusual binuclear compound [Pt2C(N═C(C6H4CON))═N(H)C6H4OMe-4}2(C≡NC6H4OMe-4)2(μ-HN═CC6H4CON)](Cl) (30) with a bridging monodeprotonated 3-iminoisoindolin-1-one, and [Pt(C6H4CONC═NH)C(N═C(C6H4CON))═N(H)C6H4OMe-4}(C≡NC6H4OMe-4)] (31), the latter resulting from the replacement of the chloro ligand in 29 by the deprotonated

  在异腈之间的反应顺式- [的MC1 2（C≡NR）2 ] [M =钯，R =赛扬1，卜吨 2，C 6 H ^ 3（2,6--ME 2）3 ; M = PT，R =赛扬4，卜吨 5，C 6 H ^ 3（2,6--ME 2）6 ]和各种未取代或取代iminoisoindolin -1-酮HN═CC 6 - [R 1 - [R 2 - [R 3 - [R 4 CONH [R 1 -R 4 = H 7; R 1，R 3，R 4＝ H，R 2＝ Me / R 1，R 2，R 4＝ H，R 3＝ Me 8（异构体混合物）；R 1，R 4＝ H，R 2，R 3＝ Cl 9 ]在回流条件下在CHCl 3中进行2小时。随后的后处理提供了配合物[的MC1 Ç（N = C（C 6 - [R 1 - [R 2 - [R 3 - [R 4 CO Ñ））= N（H）R}（C≡NR）]（M = PD，10 -18 ;
• Imino-isoindolinon-Metallkomplexe, Verfahren zu deren Herstellung, Verfahren zum Pigmentieren von hochmolekularem organischem Material und hochmolekulares organisches, einen solchen Metallkomplex enthaltendes Material
  申请人：CIBA-GEIGY AG

  公开号：EP0023889A1

  公开（公告）日：1981-02-11

  Imino-isoindolinon-Metallkomplexe der Formel worin R ein H-Atom, eine Alkylgruppe, einen Arylrest, oder einen heterocyclischen Rest, V eine direkte Bindung oder eine -NH-Gruppe, X ein H-Atom, Y ein Halogenatom, Z ein O- oder S-Atom oder eine -NH-Gruppe, M ein zweiwertiges Nicht-Erdalkalimetall, m und n 0-4 bedeuten, wobei die Summe von m und n 4 sein muß, sind wertvolle Pigmente, die Kunststoffe in farbstarken gelben Tönen von guter Licht-, Migrations-, Wetter- und Hitzeechtheit färben.

  式中的氨基-异吲哚啉酮金属配合物 其中 R 是 H 原子、烷基、芳基或杂环基，V 是直接键或 -NH 基，X 是 H 原子，Y 是卤素原子，Z 是 O 或 S 原子或 -NH 基、M 是二价非土碱金属，m 和 n 均为 0-4，其中 m 和 n 之和必须为 4。
• COLORING METHOD AND COLOR-FORMING MATERIAL
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0101741A1

  公开（公告）日：1984-03-07

  A method for coloring a material by reacting, on the material to be colored, (a) at least one aromatic isocyanate compound with (b) a > C = NH group-containing imino compound capable of reacting with the isocyanate compound to form color, and a color-forming material comprising the material carrying at least one of the compounds (a) and (b). The color formed by the reaction between the compounds (a) and (b) has excellent chemical resistance and light resistance.

  一种给材料着色的方法，在待着色的材料上，使(a)至少一种芳香族异氰酸酯化合物与(b)一种能与异氰酸酯化合物反应形成颜色的含 > C = NH 基团的亚氨基化合物反应，并形成一种着色材料，该材料包括携带(a)和(b)中至少一种化合物的材料。由化合物（a）和（b）反应形成的颜色具有优异的耐化学性和耐光性。