methyl 2-(4-bromophenyl)thiazole-4-carboxylate | 1208081-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-bromophenyl)thiazole-4-carboxylate
• 英文别名: methyl 2-(4-bromophenyl)-1,3-thiazole-4-carboxylate
• CAS: 1208081-39-3
• 化学式: C₁₁H₈BrNO₂S
• 分子量: 298.16
• InChiKey: PJHIWUICMRXOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-bromophenyl)thiazole-4-carboxylate 在 silver(I) acetate 、 palladium diacetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以87%的产率得到dimethyl 2,2'-di-(4-bromophenyl)-bis-5,5'-thiazole-4,4'-dicarboxylate
  参考文献：
  名称：

  Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.05.123
• 作为产物：
  描述：

  2-(4-Bromophenyl)-4,5-dihydrothiazole-4-carboxylic Acid 在 copper diacetate 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(4-bromophenyl)thiazole-4-carboxylate
  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

• Cobalt-Catalyzed Cross-Dehydrogenative C(sp² )−C(sp³ ) Coupling of Oxazole/Thiazole with Ether or Cycloalkane
  作者：Xiaojiao Wang、Bowen Lei、Lifang Ma、Lisi Zhu、Xinyue Zhang、Hao Zuo、Dailin Zhuang、Ziyuan Li

  DOI：10.1002/asia.201701258

  日期：2017.11.2

  Direct C5‐alkylation of oxazole/thiazole with ether or cycloalkane has been achieved through a cobalt‐catalyzed cross‐dehydrogenative coupling (CDC) process in moderate to good yields. This transformation represents the first C(sp2)−C(sp3) cross‐coupling at the C5‐position of the oxazole/thiazole via double C−H bond cleavages. Various functional groups on oxazole/thiazole substrates, as well as water

  通过钴催化的交叉脱氢偶联（CDC）工艺，恶唑/噻唑与醚或环烷烃直接进行C5-烷基化反应，产率中等至良好。这种转变代表通过双CH键断裂在恶唑/噻唑的C5位上的第一个C（sp 2）-C（sp 3）交叉偶联。简明实用的方案很好地耐受了恶唑/噻唑底物上的各种官能团，以及水和空气，构成了直接进入具有重要医学意义的杂环的方法。还提出了涉及激进过程的初步机制。
• [EN] NOVEL NK-3 RECEPTOR SELECTIVE ANTAGONIST COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN NK-3 RECEPTORS MEDIATED DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ANTAGONISTES SÉLECTIFS DU RÉCEPTEUR NK-3, COMPOSITION PHARMACEUTIQUE ET MÉTHODES POUR UNE UTILISATION DANS DES TROUBLES À MÉDIATION PAR DES RÉCEPTEURS NK-3
  申请人：EUROSCREEN SA

  公开号：WO2011121137A1

  公开（公告）日：2011-10-06

  The present invention is directed to novel compounds of formula I and their use as therapeutic compounds.

  本发明涉及公式I的新化合物及其作为治疗化合物的用途。
• NOVEL NK-3 RECEPTOR SELECTIVE ANTAGONIST COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN NK-3 RECEPTORS MEDIATED DISORDERS
  申请人：Euroscreen S.A.

  公开号：US20130023530A1

  公开（公告）日：2013-01-24

  The present invention is directed to novel compounds of formula I and their use as therapeutic compounds.

  本发明涉及一种新型化合物I的使用作为治疗化合物。
• 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.