6-methyl-3-iminoisoindolin-1-one | 127511-07-3

• 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: 6-methyl-3-iminoisoindolin-1-one
• 英文别名: 3-Imino-6-methylisoindol-1-one；3-imino-6-methylisoindol-1-one
• CAS: 127511-07-3
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: QSOBIPHMKDGPKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  6-methyl-3-iminoisoindolin-1-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 ethyl 2-cyano-2-(2,5-dimethyl-3-oxoisoindol-1-ylidene)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-氰基-5-甲基苯甲酸甲酯 生成 6-methyl-3-iminoisoindolin-1-one
  参考文献：
  名称：

  WROBEL, JAY E.

  摘要：

  DOI：

文献信息

• 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
• BICYCLIC LACTAM FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS
  申请人：Wurtz Nicholas Ronald

  公开号：US20100041664A1

  公开（公告）日：2010-02-18

  The present invention provides novel bicyclic lactams derivatives, and analogues thereof, of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables A, B, C, W, Y, Z 1 , Z 2 , Z 3 , Z 4 , R 8 , and R 9 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

  本发明提供了新型双环内酰胺衍生物及其类似物，其化学式为(I)：或其立体异构体、互变异构体、药学上可接受的盐、溶剂化物或前药。其中，变量A、B、C、W、Y、Z1、Z2、Z3、Z4、R8和R9的定义如本文所述。这些化合物是选择性因子VIIa抑制剂，可用作药物。
• Black isoindolinone pigment and coloring agent
  申请人：DAINICHISEIKA COLOR & CHEMICALS MFG. CO., LTD.

  公开号：US10723882B2

  公开（公告）日：2020-07-28

  Provided is an infrared-reflecting black isoindolinone pigment having a novel skeleton, the black isoindolinone pigment having a high blackness (coloring power) and excellent durability such as heat resistance. The black isoindolinone pigment is represented by the following formula (1), wherein each X independently represents a chlorine atom, a bromine atom, or an alkyl group, and 8≥n+m≥0.

  本发明提供了一种具有新型骨架的红外反射型黑色异吲哚啉酮颜料，该黑色异吲哚啉酮颜料具有较高的黑度（着色力）和优异的耐热性等耐久性。黑色异吲哚啉酮颜料由下式（1）表示，其中每个 X 独立地代表一个氯原子、一个溴原子或一个烷基，且 8≥n+m≥0.
• Ni^II-Mediated Coupling between Iminoisoindolinones and Nitriles Leading to Unsymmetrical 1,3,5-Triazapentadienato Complexes
  作者：Pavel V. Gushchin、Konstantin V. Luzyanin、Maximilian N. Kopylovich、Matti Haukka、Armando J. L. Pombeiro、Vadim Yu. Kukushkin

  DOI：10.1021/ic702131k

  日期：2008.4.1

  Treatment of nickel acetate Ni(OAc)(2)center dot 4H(2)O With 2 equiv of various 3-iminoisoindolin-1-ones in a suspension of RCN in the presence of triethanolamine leads to the formation of the nickel 1,3,5-triazapentadienato complexes [Ni(NH=C(R)N=C((C6RRRRCON)-R-1-R-2-R-3-C-4)}(2)] (1-17) isolated in good 50-83% yields. The reaction proceeds under relatively mild conditions (from 5 to 7 h at 25-115 degrees C, depending on the boiling point of the nitrile) and has a general character insofar as it was successfully conducted with various nitriles RCN bearing donor (R = Me, Et, Pr-n, Pr-i, Bun), weak donor (R = CH2Ph, CH2C6H4OMe-p), acceptor (R = CH2Cl, and strong acceptor (R = CCl3) groups R of different steric hindrance and also with the nonsubstituted iminoisoindolinone (3-iminoisoindolin-1-one) or the iminoisoindolinones bearing donor methyl (3-imino-5-methylisoindolin-1-one) or acceptor fluoro (4,5,6,7-tetrafluoro3-iminoisoindolin-1-one) groups in the benzene ring.
• WROEL, JAY E.
  作者：WROEL, JAY E.

  DOI：——

  日期：——