(1-phenyl-1H-imidazole-4,5-diyl)-bis-methanol | 33457-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1-phenyl-1H-imidazole-4,5-diyl)-bis-methanol
• 英文别名: [5-(Hydroxymethyl)-1-phenylimidazol-4-yl]methanol
• CAS: 33457-06-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: AOBSYJQFUUJVCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-phenyl-1H-imidazole-4,5-diyl)-bis-methanol 、 异氰酸异丙酯 在 dibutyltin diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到[1-phenyl-5-(propan-2-ylcarbamoyloxymethyl)imidazol-4-yl]methyl N-propan-2-ylcarbamate
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate 在 lithium aluminium tetrahydride 、 硝酸 、 sodium nitrite 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (1-phenyl-1H-imidazole-4,5-diyl)-bis-methanol
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023

文献信息

• 2-substituted-4, 6-diamino-s-triazine/isocyanuric acid adduct, process for synthesis of said adduct and process for curing polyepoxy resin with said adduct
  申请人：SHIKOKU CHEMICALS CORPORATION

  公开号：EP0194895A2

  公开（公告）日：1986-09-17

  Disclosed is a 2-substituted-4, 6-diamino-s-triazins/ isocyanuric acid adduct represented by the following formula: wherein R stands for an alkyl group having 2 to 20 carbon atoms, an unsubstituted or cyano group-substituted aryl group, or a group of the formula R1-CH2CH2- in which R' stands for an alkoxy group having up to 20 carbon atoms, an acyloxy group, an amino group, an N-substituted amino group, a benzotriazolyl group or a 2-alkylimidazolyl-(4)-dithiocarbonyl group, or by the following formula: wherein R2 -(CH2)m-(X)p-(CH2)m- where m is 1 or 2 p is 0 or 1 and X is imino or phenylene. When this adduct is used for curing a polyepoxy resin, a cured product having good heat resistance, insulating property and adhesion and an excellent migration-preventing effect is formed.

  本发明公开了由下式表示的 2-取代-4，6-二氨基-s-三嗪/异氰尿酸加合物： 其中R代表具有2至20个碳原子的烷基、未取代或氰基取代的芳基、或式R1- -的基团，其中R'代表具有多达20个碳原子的烷氧基、酰氧基、氨基、N-取代的氨基、苯并三唑基或2-烷基咪唑基-(4)-二硫代羰基，或由下式表示： 其中 R2-(CH2)m-(X)p-( )m- 其中 m 为 1 或 2 p 是 0 或 1，以及 X 是亚氨基或亚苯基。 使用这种加成物固化聚环氧树脂时，可形成具有良好耐热性、绝缘性和粘合性以及优异防迁移效果的固化产品。
• ANDERSON, W. K.;BHATTACHARJEE, D.;HOUSTON, D. M., J. MED. CHEM., 32,(1989) N, C. 119-127
  作者：ANDERSON, W. K.、BHATTACHARJEE, D.、HOUSTON, D. M.

  DOI：——

  日期：——
• BLEND FOR CURING EPOXY RESIN COMPOSITIONS
  申请人：Huntsman Petrochemical LLC

  公开号：EP3472221A1

  公开（公告）日：2019-04-24
• [EN] BLEND FOR CURING EPOXY RESIN COMPOSITIONS<br/>[FR] MÉLANGE POUR DURCIR DES COMPOSITIONS DE RÉSINE EPOXY
  申请人：HUNTSMAN PETROCHEMICAL LLC

  公开号：WO2017218934A1

  公开（公告）日：2017-12-21

  The present disclosure provides a curable composition that includes an epoxy resin and a curing component comprising a blend of at least two amines. The curable composition may be combined with reinforced fibers and cured to form a composite article which can be used in various applications, such as in wind turbine blades.
• [EN] UNDERFILL MATERIAL, SEMICONDUCTOR PACKAGE, AND METHOD FOR PRODUCING SEMICONDUCTOR PACKAGE<br/>[FR] MATÉRIAU DE REMPLISSAGE DIÉLECTRIQUE, BOÎTIER DE SEMI-CONDUCTEUR ET PROCÉDÉ DE PRODUCTION D'UN BOÎTIER DE SEMI-CONDUCTEUR<br/>[JA] アンダーフィル材、半導体パッケージ、及び半導体パッケージの製造方法
  申请人：SHOWA DENKO MATERIALS CO LTD

  公开号：WO2021149635A1

  公开（公告）日：2021-07-29

  アンダーフィル材は、エポキシ樹脂と、芳香族アミン硬化剤と、無機充填材と、トリアジン環とアルコキシシリル基とを有する化合物、又はトリアジン環及び一級アミノ基を有し、融点が２００℃以下である化合物と、を含有する。