2,3-dimethyl-6-nitrobenzonitrile | 15089-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-dimethyl-6-nitrobenzonitrile
• 英文别名: 3,4-dimethyl-6-nitrobenzonitrile；4,5-dimethyl-2-nitrobenzonitrile；4,5-Dimethyl-2-nitro-benzonitril；3,4-Dimethyl-6-nitrobenzonitril；4,5-Dimethyl-2-nitrobenzonitril
• CAS: 15089-77-7
• 化学式: C₉H₈N₂O₂
• mdl: MFCD09999861
• 分子量: 176.175
• InChiKey: KMXMOTHNWNJKBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-6-nitrobenzonitrile 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 2-氨基-4,5-二甲基苯甲酸
  参考文献：
  名称：

  Braendstroem,A.; Carlsson,A.I., Acta Chemica Scandinavica (1947), 1967, vol. 21, p. 983 - 992

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基邻二甲苯 在 potassium bromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 48.0h， 生成 2,3-dimethyl-6-nitrobenzonitrile
  参考文献：
  名称：

  Fischer, Alfred; Henderson, George N.; Iyer, Lokanathan M., Canadian Journal of Chemistry, 1985, vol. 63, p. 2390 - 2400

  摘要：

  DOI：

文献信息

• N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as VEGF receptor tyrosine kinase inhibitors
  申请人：——

  公开号：US20020019414A1

  公开（公告）日：2002-02-14

  1 Described are compounds of formula (I), wherein W is O or S; X is NR 8 ; Y is CR 9 R 10 -(CH 2 )n wherein R 9 and R 10 are independently of each other hydrogen or lower alkyl, and n is an integer of from and including 0 to and including 3; or Y is SO 2 ; R 1 is aryl; R 2 is a mono- or bicyclic heteroaryl group comprising one or more ring nitrogen atoms with the exception that R 2 cannot represent 2-phthalimidyl, and in case of Y═SO 2 cannot represent 2,1,3-benzothiadiazol-4-yl; any of R 3 , R 4 , R 5 and R 6 , independently of the other, is H or a substituent other than hydrogen; and R 7 and R 8 , independently of each other, are H or lower alkyl; or a N-oxide or a pharmaceutically acceptable salt thereof for the preparation of a pharmaceutical product for the treatment of a neoplastic disease which responds to an inhibition of the VEGF receptor tyrosine kinase activity. The compounds of formula (I) can be used for the treatment e.g. of a neoplastic disease, such as a tumor disease, of retinopathy and age-related macular degeneration.

  描述的是化合物的结构式（I），其中W是O或S；X是NR8；Y是CR9R10-(CH2)n，其中R9和R10彼此独立地是氢或较低的烷基，n是从0到3的整数；或Y是SO2；R1是芳基；R2是一个含有一个或多个环氮原子的单环或双环杂环基团，但R2不能代表2-邻苯二甲酰胺，并且在Y为SO2的情况下不能代表2,1,3-苯并噻二唑-4-基；R3、R4、R5和R6中的任何一个，独立于其他，是H或除氢之外的取代基；R7和R8，彼此独立地是H或较低的烷基；或其N-氧化物或药用可接受的盐，用于制备用于治疗对VEGF受体酪氨酸激酶活性抑制产生反应的恶性疾病的药物产品。结构式（I）的化合物可用于治疗恶性疾病，如肿瘤疾病，视网膜病和老年性黄斑变性等。
• Electrophilic aromatic substitution. Part 29. The kinetics and products of the solvolyses in aqueous sulphuric acids of 2-cyano-3,4-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate: the non-occurrence of an intramolecular 1,3-migration of the nitro-group in the solvolytic reactions of the diene. The kinetics and products of nitration of 2,3-and 3,4-dimethylbenzonitrile
  作者：Colin Bloomfield、Roy B. Moodie、Kenneth Schofield

  DOI：10.1039/p29830001003

  日期：——

  rearrangement of the nitro-group and the observed 1,3-rearrangement of the diene to give 2,3-dimethyl-5-nitrobenzonitrile under non-solvolytic conditions appears to be a thermal reaction of the diene molecule. By combining the solvolysis results with those for the nitration of 2,3-dimethylbenzonitrile in 70.4–82.5% H2SO4 it is shown that the major primary consequence of the nitration is ipso-attack and

  在61.8-79.5％H动力学2 SO 4和产物形成在61.8-84.3％H 2 SO 4为上述命名二烯的solvolyses已被确定。该反应被解释为涉及亚硝酸并发消除和甲AL相同的1代本位-中间体在2,3-二甲基苄腈的硝化反应中产生。该中间体通过分子间重排反应（通过与2,3-二甲基苄腈的溶剂分解分离和通过与4-氟苯酚反应捕获硝基离子来证明），通过水的亲核捕获以及通过1,2-分子内重排反应2，3-二甲基-4-硝基苄腈。结果允许总溶剂分解速率系数的分配，并证明与A AL 1反应一样，与消除竞争的反应的衍生系数取决于酸度。亚硝酸的消除也是酸催化的，可能不是简单的E1反应。二烯的溶剂分解反应不会导致硝基的1,3-分子内重排，并且在非溶剂化条件下，观察到的二烯的1,3-重排产生了2,3-二甲基-5-硝基苯甲腈是二烯分子的热反应。通过溶剂分解结果与2,3-二甲基苄腈的硝化在70.4-82.5％组合ħ
• Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios
  作者：Xinhua Peng、Naoyuki Fukui、Masayuki Mizuta、Hitomi Suzuki

  DOI：10.1039/b301847d

  日期：——

  and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and molecular oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodology based on nitric and sulfuric acids. In some cases, the minor isomer became favoured to a significant extent, resulting in the reversal of ordinary isomer ratios

  在沸石的存在下，通过二氧化氮和分子氧的共同作用，可以在室温下将中等程度失活的芳烃（例如1-硝基萘，萘腈和甲基化的苄腈）平稳地硝化。与基于硝酸和硫酸的常规硝化方法相比，区域选择性显着提高。在某些情况下，次要异构体在很大程度上受到青睐，导致硝化产物的普通异构体比率逆转。
• Process of Preparing a Quinazoline Derivative
  申请人：SCINOPHARM (CHANGESHU) OHARMACEUTICALS, LTD.

  公开号：US20160200688A1

  公开（公告）日：2016-07-14

  A concise, efficient and cost- and time-saving process for the preparation of a quinazoline derivative of formula A given below: which is an intermediate for making gefitinib or gefitinib itself, comprising reacting a compound of Formula B: with 3-chloro-4-fluoroaniline (VI) in the presence of a N,N-dialkyl formamide acetal, a Bronsted acid catalyst, and a solvent in a one-pot reaction.

  一种制备以下式子A的喹唑啉衍生物的简洁、高效、节约成本和时间的方法： 其中A是制备吉非替尼或吉非替尼中间体的一种，包括在N，N-二烷基甲酰胺缩醛、布朗斯特酸催化剂和溶剂的存在下，将式子B的化合物与3-氯-4-氟苯胺（VI）在单锅反应中反应。
• [EN] N-ARYL(THIO)ANTHRANILIC ACID AMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS VEGF RECEPTOR TYROSINE KINASE INHIBITORS<br/>[FR] DERIVES DE N-ARYL(THIO)ANTHRANILIQUE ACIDE AMIDE, LEUR PREPARATION ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA TYROSINE KINASE DU RECEPTEUR VEGF
  申请人：NOVARTIS AG

  公开号：WO2000027820A1

  公开（公告）日：2000-05-18

  Described are compounds of formula (I), wherein W is O or S; X is NR8; Y is CR9R10-(CH2)n wherein R9 and R10 are independently of each other hydrogen or lower alkyl, and n is an integer of from and including 0 to and including 3; or Y is SO2; R1 is aryl; R2 is a mono- or bicyclic heteroaryl group comprising one or more ring nitrogen atoms with the exception that R2 cannot represent 2-phthalimidyl, and in case of Y = SO2 cannot represent 2,1,3-benzothiadiazol-4-yl; any of R3, R4, R5 and R6, independently of the other, is H or a substituent other than hydrogen; and R7 and R8, independently of each other, are H or lower alkyl; or a N-oxide or a pharmaceutically acceptable salt thereof for the preparation of a pharmaceutical product for the treatment of a neoplastic disease which responds to an inhibition of the VEGF receptor tyrosine kinase activity. The compounds of formula (I) can be used for the treatment e.g. of a neoplastic disease, such as a tumor disease, of retinopathy and age-related macular degeneration.

  本文描述了式(I)的化合物，其中W是O或S；X是NR8；Y是CR9R10-(CH2)n，其中R9和R10独立地是氢或低级烷基，n是0至3的整数；或者Y是SO2；R1是芳基；R2是一个含有一个或多个环氮原子的单环或双环杂环基团，但R2不能代表2-苯甲酰亚胺基，且在Y = SO2的情况下不能代表2,1,3-苯并噻二唑-4-基；R3、R4、R5和R6中的任何一个，除了氢之外，都是取代基；R7和R8独立地是氢或低级烷基；或其N-氧化物或药学上可接受的盐，用于制备用于治疗对VEGF受体酪氨酸激酶活性抑制有反应的肿瘤疾病的制药产品。式(I)的化合物可用于治疗肿瘤疾病、视网膜病变和年龄相关性黄斑变性等疾病。