5-methyl-3-iminoisoindolin-1-one | 1015228-02-0

• 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-methyl-3-iminoisoindolin-1-one
• 英文别名: 3-Imino-5-methylisoindol-1-one；3-imino-5-methylisoindol-1-one
• CAS: 1015228-02-0
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: GKZGKHCTVMKEKY-UHFFFAOYSA-N

物化性质

• 沸点：
  355.5±35.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

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：

  cis-[PdCl₂(CN(t-Bu))₂] 、 5-methyl-3-iminoisoindolin-1-one 以 氯仿 为溶剂， 生成 [PdCl(C(N=C(C6H3(Me)CON)=N(H)-t-Bu)(CN-t-Bu)]
  参考文献：
  名称：

  3-Iminoisoindolin-1-ones和复杂的异腈之间的偶联作为金属介导的新型钯和铂亚氨基卡宾物种的金属介导途径。

  摘要：

  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 ;

  DOI：

  10.1021/om800517c
• 作为产物：
  描述：

  4-甲基邻苯二腈 在 二乙基羟胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 5-methyl-3-iminoisoindolin-1-one 、 6-methyl-3-iminoisoindolin-1-one
  参考文献：
  名称：

  通过N，N-二乙基羟胺促进邻苯二甲腈转化转化酞菁和3-Iminoisoindolin-1-one的新颖而温和的路线和反应的显着溶剂依赖性

  摘要：

  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

  DOI：

  10.1002/adsc.200700261

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。
• BLACK ISOINDOLINONE PIGMENT AND COLORING AGENT
  申请人：Dainichiseika Color & Chemicals Mfg. Co., Ltd.

  公开号：EP3569659A1

  公开（公告）日：2019-11-20

  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.
• 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.
• 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