dimethyl 2,2'-diphenyl-bis-5,5'-thiazole-4,4'-dicarboxylate | 1315510-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 2,2'-diphenyl-bis-5,5'-thiazole-4,4'-dicarboxylate
• 英文别名: Methyl 5-(4-methoxycarbonyl-2-phenyl-1,3-thiazol-5-yl)-2-phenyl-1,3-thiazole-4-carboxylate；methyl 5-(4-methoxycarbonyl-2-phenyl-1,3-thiazol-5-yl)-2-phenyl-1,3-thiazole-4-carboxylate
• CAS: 1315510-22-5
• 化学式: C₂₂H₁₆N₂O₄S₂
• 分子量: 436.512
• InChiKey: MBSXZKFKFIOBNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate 在 silver(I) acetate 、 copper diacetate 、 caesium carbonate 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.0h， 生成 dimethyl 2,2'-diphenyl-bis-5,5'-thiazole-4,4'-dicarboxylate
  参考文献：
  名称：

  Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage

  摘要：

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。

  DOI：

  10.1039/c2cc00081d

文献信息

• Palladium(II)-catalyzed oxidative Heck coupling of thiazole-4-carboxylates
  作者：Ziyuan Li、Ling Ma、Changhua Tang、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1016/j.tetlet.2011.08.088

  日期：2011.10

  Oxidative Heck coupling of thiazole-4-carboxylates via palladium(II)-catalyzed C-H bond activation has been achieved in moderate to good yields. No ligand, and no acidic additive were used in the reaction. The results showed that this protocol tolerated a series of substitutions on the thiazole ring. A preliminary attempt of direct arylation with p-xylene via Pd(II)-catalyzed C-H bond activation has also been done. (C) 2011 Elsevier Ltd. All rights reserved.
• Aryl–aryl coupling via palladium-catalyzed C–P/C–H bond cleavage
  作者：Ziyuan Li、Haipin Zhou、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1016/j.tet.2013.02.001

  日期：2013.4

  The first example of aryl-aryl coupling through palladium-catalyzed C-P/C-H bond cleavage with good functional group tolerance is disclosed. This work demonstrates the phosphines could be used as coupling partners in palladium-catalyzed aryl-aryl coupling. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives
  作者：Ziyuan Li、Yiyun Wang、Yue Huang、Changhua Tang、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1016/j.tet.2011.05.123

  日期：2011.8

  An efficient Pd(OAc)(2)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives is described. It represents a facile and practical methodology to prepare bis-5,5'-thiazole (oxazole)-4,4'-dicarboxylic derivatives in good to excellent yields. This protocol tolerates a series of substitutions on the thiazole (oxazole) rings, including alkyl, carbonyl, and electron-withdrawing/donating group substituted phenyl groups. (C) 2011 Elsevier Ltd. All rights reserved.
• Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage
  作者：Ziyuan Li、Ling Ma、Jinyi Xu、Lingyi Kong、Xiaoming Wu、Hequan Yao

  DOI：10.1039/c2cc00081d

  日期：——

  The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C–H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance.

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。