6-氨基-2,3-二甲基苯酚 | 23363-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 6-氨基-2,3-二甲基苯酚
• 英文名称: 5,6-dimethyl-2-aminophenol
• 英文别名: 6-Amino-2,3-dimethyl-phenol；6-Amino-2,3-dimethylphenol
• CAS: 23363-74-8
• 化学式: C₈H₁₁NO
• mdl: MFCD07403492
• 分子量: 137.181
• InChiKey: ZRTQIWOAHUHCJE-UHFFFAOYSA-N

物化性质

• 沸点：
  252.5±28.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  5,8-喹啉二酮 、 6-氨基-2,3-二甲基苯酚 在 cobalt(II) acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以31%的产率得到8,9-Dimethylpyrido[3,2-a]phenoxazin-5-one
  参考文献：
  名称：

  Antitumor Agents. 5. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Dimethyl-5H-pyridophenoxazin-5-ones, Tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-Benzopyridophenoxazin-5-ones with Potent Antiproliferative Activity

  摘要：

  New antiproliferative compounds, dimethyl-5H-pyrido[3,2-a] phenoxazin-5-ones (1-6), tetrahydro-5-Hbenzopyrido[2,3-j]phenoxazin-5-ones (7-9), and 5H-benzopyrido[3,2-a] phenoxazin-5-ones (10-12) were synthesized and evaluated against representative human neoplastic cell lines. Dimethyl derivatives 1-6 were more active against carcinoma than leukemia cell lines. The tetrahydrobenzo derivatives 7-9 were scarcely active, whereas the corresponding benzo derivatives 10-12 showed notable cytotoxicity against a majority of the tested cell lines. Molecular modeling studies indicated that the high potency of 10 and 11, the most cytotoxic compounds of the whole series, could be due to the position of the condensed benzene ring, which favors d-d stacking interactions with purine and pyrimidine bases in the DNA active site. Biological studies suggested that 10-12 have no effect on human topoisomerases I and II and that they induce arrest at the G2/M phase.

  DOI：

  10.1021/jm050745l
• 作为产物：
  描述：

  2,3-二甲基-6-硝基苯酚 在 sodium hydroxide 、 sodium tetrahydroborate 、 palladium on activated charcoal 作用下， 生成 6-氨基-2,3-二甲基苯酚
  参考文献：
  名称：

  Antitumor Agents. 5. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Dimethyl-5H-pyridophenoxazin-5-ones, Tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-Benzopyridophenoxazin-5-ones with Potent Antiproliferative Activity

  摘要：

  New antiproliferative compounds, dimethyl-5H-pyrido[3,2-a] phenoxazin-5-ones (1-6), tetrahydro-5-Hbenzopyrido[2,3-j]phenoxazin-5-ones (7-9), and 5H-benzopyrido[3,2-a] phenoxazin-5-ones (10-12) were synthesized and evaluated against representative human neoplastic cell lines. Dimethyl derivatives 1-6 were more active against carcinoma than leukemia cell lines. The tetrahydrobenzo derivatives 7-9 were scarcely active, whereas the corresponding benzo derivatives 10-12 showed notable cytotoxicity against a majority of the tested cell lines. Molecular modeling studies indicated that the high potency of 10 and 11, the most cytotoxic compounds of the whole series, could be due to the position of the condensed benzene ring, which favors d-d stacking interactions with purine and pyrimidine bases in the DNA active site. Biological studies suggested that 10-12 have no effect on human topoisomerases I and II and that they induce arrest at the G2/M phase.

  DOI：

  10.1021/jm050745l

文献信息

• BROADSPECTRUM 2-AMINO-BENZOXAZOLE SULFONAMIDE HIV PROTEASE INHIBITORS
  申请人：SURLERAUX Dominique Louis Nestor Ghislain

  公开号：US20100029632A1

  公开（公告）日：2010-02-04

  The present invention concerns the compounds having the formula N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein R 1 and R 8 each are H, optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, aryl, Het 1 , Het 2 ; R 1 may also be a radical of formula (R 11a R 11b )NC(R 10a R 10b )CR 9 —; t is 0, 1 or 2; R 2 is H or C 1-6 alkyl; L is —C(═O)—, —O—C(═O)—, —NR 8 —C(═O)—, —O—C 1-6 alkanediyl-C(═O)—, —NR 8 —C 1-6 alkanediyl-C(═O)—, —S(═O) 2 —, —O—S(═O) 2 —, —NR 8 —S(═O) 2 ; R 3 is C 1-6 alkyl, aryl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, or arylC 1-4 alkyl; R 4 is H, C 1-4 alkylOC(═O), carboxyl, aminoC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl or optionally substituted C 1-6 alkyl; R 5 and R 6 are H or C 1-6 alkyl. It further relates to their use as broadspectrum HIV protease inhibitors, processes for their preparation as well as pharmaceutical compositions and diagnostic kits comprising them. It also concerns combinations thereof with another anti-retroviral agent, and to their use in assays as reference compounds or as reagents.

  本发明涉及具有以下公式的化合物：N-氧化物、盐、立体异构体、混合物、前药、酯及其代谢物，其中R1和R8分别为H、可选取代的C1-6烷基、C2-6烯基、C3-7环烷基、芳基、Het1、Het2；R1还可以是公式（R11aR11b）NC（R10aR10b）CR9—的基团；t为0、1或2；R2为H或C1-6烷基；L为—C（═O）—、—O—C（═O）—、—NR8—C（═O）—、—O—C1-6烷二基-C（═O）—、—NR8—C1-6烷二基-C（═O）—、—S（═O）2—、—O—S（═O）2—、—NR8—S（═O）2；R3为C1-6烷基、芳基、C3-7环烷基、C3-7环烷基C1-4烷基或芳基C1-4烷基；R4为H、C1-4烷基OC（═O）、羧基、氨基C（═O）、单烷基或二烷基氨基C（═O）、C3-7环烷基、C2-6烯基、C2-6炔基或可选取代的C1-6烷基；R5和R6为H或C1-6烷基。本发明还涉及它们作为广谱HIV蛋白酶抑制剂的用途，以及它们的制备方法、包含它们的制药组合物和诊断试剂盒。它还涉及与其他抗逆转录病毒药物的组合，以及它们作为参考化合物或试剂在检测中的使用。
• Procédé de préparation de dérivés benzéniques par réaction d'un halogénobenzène activé avec un réactif organique anionique oxygéné ou soufré
  申请人：RHONE-POULENC SPECIALITES CHIMIQUES

  公开号：EP0022387A1

  公开（公告）日：1981-01-14

  L'invention a pour object un procédé de préparation de composés benzéniques par réaction d'un halogénobenzène activé avec un réactif organique anionique oxygéné ou soufré caractérisé en ce que la réaction a lieu en présence d'au moins un agent séquestrant de formule : dans laquelle n est un nombre entier supérieur ou égal à 0 et inférieur ou égal à environ 10 (0≤n≤10), R1 R2 R3 et R, identiques ou différents représentent un atome d'hydrogène ou un radical alkyle ayant de 1 à 4 atomes de carbone et R, représente un radical alkyle ou cycloalkyle ayant de 1 à 12 atomes de carbone, un radical phényle ou un radical -CmH2m-Ø ou CmH2m+1-Ø-, où m est compris entre 1 et 12. Les composés obtenus selon l'invention sont utiles notamment en tant qu'intermédiaires pour la synthèse de composés organiques utilisables comme agents phytosanitaires.

  本发明的目的是一种通过活化卤苯与含氧或含硫阴离子有机试剂反应制备苯化合物的工艺，其特征在于该反应是在至少一种式......的螯合剂存在下进行的： 式中 n 是大于或等于 0 且小于或等于约 10 的整数（0≤n≤10），R1、R2、R3 和 R（相同或不同）代表氢原子或具有 1 至 4 个碳原子的烷基，R 代表具有 1 至 12 个碳原子的烷基或环烷基、苯基或 -CmH2m-Ø- 或 CmH2m+1-Ø- 基，其中 m 在 1 和 12 之间。 根据本发明获得的化合物尤其可用作合成可用作植物保护剂的有机化合物的中间体。
• A process for preparing glycidyl derivatives of compounds having at least one aromatic hydroxyl group or aromatic amine group
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0103282A2

  公开（公告）日：1984-03-21

  This invention is directed to a process for preparing glycidyl derivatives of compounds having at least one aromatic hydroxyl group or aromatic amine group per molecule by reacting at least one compound having at least one aromatic hydroxyl group or aromatic amine group per molecule with an excess of at least one epihalohydrin in the presence of an alkali metal hydroxide and subsequently recovering the glycidyl derivative product. The process is characterized by (1) conducting the reaction in the presence of an organic solvent which codistills with water and said epihalohydrin at a boiling point below the boiling point of the lowest boiling compound among the components in the reaction mixture: (2) conducting the reaction at a temperature and a reduced pressure sufficient to provide a distillate with a boiling point of from 45°C to 80°C. (3) employing said alkali metal hydroxide as an aqueous solution and adding said aqueous alkali metal hydroxide in a continuous manner over a period of from 0.5 to 10 hours. (4) continuously removing water by means of codistillation at a rate such that the water content of the reaction mixture is less than 6 percent by weight: and (5) separating the water from the condistulate and returning the solvent and epihalohydrin to the reaction mixture. The process of this invention maximizes the epthalo- hydrin yields and produces epoxy resins low in hydrolyzable halide.

  本发明涉及一种制备每分子至少有一个芳香羟基或芳香胺基团的化合物的缩水甘油衍生物的工艺，其方法是在碱金属氢氧化物存在下，使至少一种每分子至少有一个芳香羟基或芳香胺基团的化合物与过量的至少一种表卤代烃反应，然后回收缩水甘油衍生物产物。该工艺的特点是：(1) 在有机溶剂存在下进行反应，该有机溶剂与水和所述表卤代烃的沸点低于反应混合物中组分的最低沸点化合物的沸点：(2) 在足以提供沸点为 45°C 至 80°C 的蒸馏物的温度和减压下进行反应。(3) 使用所述碱金属氢氧化物作为水溶液，并在 0.5 至 10 小时内连续加入所述碱金属氢氧化物水溶液。(4) 以反应混合物中水含量低于 6%（重量百分比）的速度，通过蒸馏连续去除水： (5) 将水从冷凝物中分离出来，并将溶剂和表氢醇返回到反应混合物中。本发明的工艺最大限度地提高了表卤代烃的产量，并生产出低水解卤化物含量的环氧树脂。
• Preparation of epoxy resins
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0264760A2

  公开（公告）日：1988-04-27

  An improved process for the preparation of epoxy resins comprising reacting at least one epihalohydrin with at least one aromatic material containing an active hydrogen atom reactive with an epihalohydrin in the presence of an organic solvent, an alkali metal hydroxide and optionally in the presence of a catlyast for the reaction between the aromatic active hydrogen-containing material and the epihalohydrin while controlling the concentration of water in the reaction mixture. The improvement comprises (1) drying the reaction mixture after completion of the reaction with the concentration of water is equal to or less than 2 percent by weight; (2) removing any insoluble materials from the reaction mixture by any suitable mechanical solid separation means thereby forming a resin/epihalohydrin/organic solvent mixture essentially free of insoluble material; (3) washing the resin/epihalohydrin/organic solvent material with water, so as to remove water soluble materials; (4) drying the resin/epihalohydrin/organic solvent mixture to a water content equal to or less than 2 percent by weight; and (5) recovering the resultant epoxy resin from the resin/epihalohydrin/organic solvent mixture by an suitable means. The present process maximizes epihlaohydrin yields and also produces epoxy resins low in hydrolyzable halide and total halide.

  一种制备环氧树脂的改进工艺，包括在有机溶剂、碱金属氢氧化物和可选的催化剂存在下，使至少一种环卤海德林与至少一种含活性氢原子的芳香族材料反应，使芳香族活性含氢材料与环卤海德林反应，同时控制反应混合物中水的浓度。改进包括：(1) 在反应完成后，干燥反应混合物，水的浓度等于或小于 2%（重量百分比）；(2) 通过任何合适的机械固体分离手段，从反应混合物中去除任何不溶性物质，从而形成基本上不含不溶性物质的树脂/表卤代醇/有机溶剂混合物；(3) 用水洗树脂/环糊精/有机溶剂材料，以除去水溶性物质； (4) 干燥树脂/环糊精/有机溶剂混合物，使其含水量等于或小于 2%（重量比）； (5) 通过适当的方法从树脂/环糊精/有机溶剂混合物中回收所得环氧树脂。本工艺最大限度地提高了环氧氯丙烷的产量，同时还生产出了可水解卤化物和总卤化物含量较低的环氧树脂。
• Polymer having dihydropyridine rings or dihydrotriazine rings, process for producing the same, and applications thereof
  申请人：HITACHI, LTD.

  公开号：EP0295381A1

  公开（公告）日：1988-12-21

  A polymer having dihydropyridine rings or dihydrotriazine rings as main constitutional units, as ethynyl- or cyanato-terminated Schiff's compound which is a starting material for producing the polymer, and applications of the polymer.

  一种以二氢吡啶环或二氢三嗪环为主要结构单元的聚合物，作为生产该聚合物的起始材料的乙炔或氰基端希夫化合物，以及该聚合物的应用。