1-[(3,4-二甲基苯基)甲基]咪唑 | 70759-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(3,4-二甲基苯基)甲基]咪唑
• 英文名称: 1-(1H-Imidazol-1-yl)methyl-3,4-dimethylbenzene
• 英文别名: 1-(3,4-dimethylbenzyl)imidazole；1-[(3,4-dimethylphenyl)methyl]imidazole
• CAS: 70759-03-4
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: ZQIMOEUCLLSGCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  富马酸 、 1-[(3,4-二甲基苯基)甲基]咪唑 在 乙酸乙酯 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以afforded 1-(3,4-dimethylbenzyl)imidazole hydrogen fumarate 1/6 hydrate as a white solid m.p. 138°-140°的产率得到1-(3,4-dimethylbenzyl)imidazole hydrogen fumarate
  参考文献：
  名称：

  1-[3-(2,4-Dichlorophenyl)propyl]imidazole and salts thereof

  摘要：

  一种治疗或预防哺乳动物或哺乳动物组织血栓栓塞疾病（ii）预防、治疗或预防心绞痛，或（iii）预防或延迟休克发生的方法，包括向哺乳动物或哺乳动物组织施用式中的非毒性有效量咪唑化合物：## STR1 ## 其中A是1到3个碳原子的直链或支链、饱和或不饱和的无环烃基，n为0或1，R为## STR2 ## 其中m为0或至少为1的整数，每个Q取代基（当m大于1时可能相同或不同）从1到4个碳原子的饱和或不饱和的烃基；1到4个碳原子的烷氧基；硝基；苯基；酰氧基；卤基；三卤甲基；羟基；羧基；此类羧基的盐；羧基烷氧基；羧基芳氧基；羧基芳基烷氧基；-NR.sup.6 R.sup.7和-CONR.sup.6 R.sup.7，其中R.sup.6和R.sup.7可能相同或不同，每个都是氢或1到4个碳原子的烷基；咪唑化合物是其自由碱基或药学上可接受的盐。该类咪唑化合物的药物制剂也是新颖的。提供了制备咪唑化合物的方法。

  公开号：

  US04431815A1
• 作为产物：
  描述：

  3,4-二甲基氯苄 在 sodium carbonate 、 sodium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 1-[(3,4-二甲基苯基)甲基]咪唑
  参考文献：
  名称：

  An improved and convenient procedure for the synthesis of 1-substituted imidazoles.

  摘要：

  1-保护的咪唑类化合物，如1-乙酰咪唑和1-苯甲酰咪唑，与各种卤化物反应，如苄基、烯丙基、α-酮和烷基卤化物，能够高产率地得到1-保护的3-取代咪唑鎓盐。所得到的咪唑鎓盐可以通过水或醇处理轻易去保护，进而获得相应的1-取代咪唑类化合物，产率极高。在这个反应中，1-取代咪唑的产率因所使用的卤化物种类和/或保护基团的不同而变化，产率按以下顺序递增：苄基卤化物 ≥ 烯丙基卤化物 ∼ α-酮卤化物 < 烷基卤化物，并且乙酰基 ≥ 苯甲酰基 < 乙氧羰基 < 二乙氧基甲基 < 三甲基硅基 < 对甲苯磺酰基。

  DOI：

  10.1248/cpb.31.1213

文献信息

• High-Yield Synthesis of Novel Imidazoles and Triazoles from Alcohols and Phenols
  作者：Vincent C. O. Njar

  DOI：10.1055/s-2000-8722

  日期：——

  A variety of alcohols and phenols are converted into their corresponding imidazoles and triazoles in high yields by a facile reaction with N,N 1-carbonyldiimidazole (CDI) or N,N 1-carbonylditriazole (CDT) in acetonitrile. The reactions of allylic alcohols, enols and phenols with CDI or CDT are unprecedented. Evidence is provided which suggests that the reaction with alcohols proceeds via the corresponding carbamates by an SNi mechanism.

  多种醇和酚在乙腈中通过与N，N'-羰基二咪唑（CDI）或N，N'-羰基二三唑（CDT）的简便反应，高效地转化为相应的咪唑和三唑。烯丙醇、烯醇和酚与CDI或CDT的反应是前所未有的。有证据表明，醇的反应是通过相应的氨基甲酸酯经由SNi机理进行的。
• The Reaction of Carbonyldiimidazole with Alcohols to Form Carbamates and<i>N-</i>Alkylimidazoles
  作者：Jonathan L. Vennerstrom、Yuanqing Tang、Yuxiang Dong

  DOI：10.1055/s-2004-831215

  日期：——

  The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 °C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower

  非苄基伯醇和仲脂肪醇与羰基二咪唑 (CDI) 的反应得到相应的氨基甲酸酯，但没有得到 N-烷基咪唑。对于苄基伯醇，N-烷基咪唑的形成合理地在 170 °C 下在几种不同的溶剂中进行，并通过最初形成的氨基甲酸酯发生。然而，在这些相当强制的条件下，甚至在较低的反应温度下，消除对于具有 β-氢原子的苄基仲醇来说是一个重要的副反应。除了一个例外，六种 N,N-二取代的 β-氨基醇与 CDI 形成 N-烷基咪唑的反应在相对温和的条件下进行，并且可能通过氮丙啶中间体发生。
• Imidazole derivatives and salts thereof
  申请人：Burroughs Wellcome Co.

  公开号：US04396771A1

  公开（公告）日：1983-08-02

  1-Substituted-imidazoles of the formula: ##STR1## in which A is selected from the group consisting of straight or branched, saturated or unsaturated, acyclic hydrocarbon radicals of from 1 to 3 carbon atoms and R is ##STR2## wherein n is an integer which is at least 1, and the or each Q substituent, which when n is greater than 1 may be the same or different, is selected from a saturated alkyl group of from 1 to 4 carbon atoms or an unsaturated alkyl group of from 2 to 4 carbon atoms, with the proviso that when A is unsaturated Q may also be selected from alkoxy of from 1 to 4 carbon atoms; halo; trihalomethyl; hydroxy; carboxyl; a salt of such a carboxyl group; carboalkyloxy; carboaryloxy; carboarylalkyloxy; --NR.sup.6 R.sup.7 or --CONR.sup.6 R.sup.7 ; in which R.sup.6 and R.sup.7 may be the same or different and are hydrogen or alkyl of from 1 to 4 carbon atoms; the 1-substituted-imidazole being the free base or an acid addition salt thereof. Methods of preparing the 1-substituted-imidazoles are also provided. The imidazoles have pharmacological properties that make them of use in the treatment of thromboembolic disorders, shock and angina pectoris.

  式子如下：##STR1## 其中，A选自由1到3个碳原子的直链或支链、饱和或不饱和的脂肪烃基团组成的群，R为##STR2## 其中n是至少为1的整数，当n大于1时，每个Q取代基可以相同或不同，选自由1到4个碳原子的饱和烷基或2到4个碳原子的不饱和烷基，但当A为不饱和时，Q还可以选自1到4个碳原子的烷氧基、卤素、三卤甲基、羟基、羧基、该羧基的盐、羧基烷氧基、羧基芳氧基、羧基芳基烷氧基、--NR.sup.6 R.sup.7或--CONR.sup.6 R.sup.7，其中R.sup.6和R.sup.7可以相同或不同，选自氢或1到4个碳原子的烷基；该1-取代咪唑为其自由碱基或酸加合盐。本文还提供了制备1-取代咪唑的方法。这些咪唑具有药理特性，可用于治疗血栓栓塞性疾病、休克和心绞痛。
• Imidazole derivatives for treating myocardial infarction
  申请人：Burroughs Wellcome Co.

  公开号：US04405634A1

  公开（公告）日：1983-09-20

  1-Substituted-imidazoles of the formula: ##STR1## in which A is selected from the group consisting of straight or branched, saturated or unsaturated, acyclic hydrocarbon radicals of from 1 to 3 carbon atoms and R is ##STR2## wherein n is an integer which is at least 1, and the or each Q substituent, which when n is greater than 1 may be the same or different, is selected from a saturated alkyl group of from 1 to 4 carbon atoms or an unsaturated alkyl group of from 2 to 4 carbon atoms, with the proviso that when A is unsaturated Q may also be selected from alkoxy of from 1 to 4 carbon atoms; halo; trihalomethyl; hydroxy; carboxyl; a salt of such a carboxyl group; carboalkyloxy; carboaryloxy; carboarylalkyloxy; --NR.sup.6 R.sup.7 or --CONR.sup.6 R.sup.7 ; in which R.sup.6 and R.sup.7 may be the same or different and are hydrogen or alkyl of from 1 to 4 carbon atoms; the 1-substituted-imidazole being the free base or an acid addition salt thereof. Methods of preparing the 1-substituted-imidazoles are also provided. The imidazoles have pharmacological properties that make them of use in the treatment of thromboembolic disorders, shock and angina pectoris.

  公式为：##STR1## 其中A从1到3个碳原子的直链或支链、饱和或不饱和的脂肪烃基团中选择，R为##STR2## 其中n是至少为1的整数，当n大于1时，每个Q取代基可以相同或不同，从1到4个碳原子的饱和烷基或2到4个碳原子的不饱和烷基中选择，但当A为不饱和时，Q也可以从1到4个碳原子的烷氧基、卤素、三卤甲基、羟基、羧基、羧基盐、羧基烷氧基、羧基芳氧基、羧基芳基烷氧基、--NR.sup.6 R.sup.7或--CONR.sup.6 R.sup.7中选择，其中R.sup.6和R.sup.7可以相同或不同，是氢或从1到4个碳原子的烷基。1-取代咪唑是其自由碱或酸加成盐。还提供了制备1-取代咪唑的方法。咪唑具有药理学性质，可用于治疗血栓栓塞性疾病、休克和心绞痛。
• 1-[3-(2,4-Dichlorophenyl)propyl]imidazole and salts thereof
  申请人：Burroughs Wellcome Co.

  公开号：US04431815A1

  公开（公告）日：1984-02-14

  A method for (i) the treatment or prophylaxis of a thrombo-embolic disorder of a mammal or a mammalian tissue (ii) the prevention, treatment or prophylaxis of angina pectoris, or (iii) the prevention or delay of the onset of shock, which comprises the administration to the mammal or mammalian tissue of a non-toxic, effective amount of an imidazole of the formula: ##STR1## in which A is a straight or branched, saturated or unsaturated acyclic hydrocarbon radical of from 1 to 3 carbon atoms, n is 0 or 1, and R is ##STR2## wherein m is 0 or an integer which is at least 1 and the or each Q substituent, which, when m is greater than 1 may be the same or different is selected from a saturated or unsaturated hydrocarbon group of from 1 to 4 carbon atoms; alkoxy of from 1 to 4 carbon atoms; nitro; phenyl; acyloxy; halo; trihalomethyl; hydroxy; carboxyl; a salt of such a carboxyl group; carboalkyloxy; carboaryloxy; carboarylalkyloxy; --NR.sup.6 R.sup.7 and --CONR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 may be the same or different and are each hydrogen or alkyl of from 1 to 4 carbon atoms; the imidazole being the free base or a pharmaceutically acceptable salt thereof. Pharmaceutical formulations of some inidazoles within the class suitable for use in the method of treatment are also novel. Methods of preparing the imidazoles are provided.

  一种治疗或预防哺乳动物或哺乳动物组织血栓栓塞疾病（ii）预防、治疗或预防心绞痛，或（iii）预防或延迟休克发生的方法，包括向哺乳动物或哺乳动物组织施用式中的非毒性有效量咪唑化合物：## STR1 ## 其中A是1到3个碳原子的直链或支链、饱和或不饱和的无环烃基，n为0或1，R为## STR2 ## 其中m为0或至少为1的整数，每个Q取代基（当m大于1时可能相同或不同）从1到4个碳原子的饱和或不饱和的烃基；1到4个碳原子的烷氧基；硝基；苯基；酰氧基；卤基；三卤甲基；羟基；羧基；此类羧基的盐；羧基烷氧基；羧基芳氧基；羧基芳基烷氧基；-NR.sup.6 R.sup.7和-CONR.sup.6 R.sup.7，其中R.sup.6和R.sup.7可能相同或不同，每个都是氢或1到4个碳原子的烷基；咪唑化合物是其自由碱基或药学上可接受的盐。该类咪唑化合物的药物制剂也是新颖的。提供了制备咪唑化合物的方法。