methyl 2-(4-nitrophenyl)thiazole-4-carboxylate | 1340599-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(4-nitrophenyl)thiazole-4-carboxylate
• 英文别名: methyl 2-(4-nitrophenyl)-1,3-thiazole-4-carboxylate
• CAS: 1340599-26-9
• 化学式: C₁₁H₈N₂O₄S
• mdl: MFCD24868297
• 分子量: 264.262
• InChiKey: NDYMJHOKDAJPCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 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：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-nitrophenyl)thiazole-4-carboxylate 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到Methyl 2-(4-aminophenyl)-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  The Synthesis and Biological Evaluation of Anithiactin A/Thiasporine C and Analogues

  摘要：

  Anithiactin A 的合成分为四个步骤。合成了几种密切相关的类似物，并评估了它们对结肠癌和乳腺癌细胞系的生物活性。结果发现，即使在高浓度（100 μM）下，连翘素 A 也没有细胞毒性；但是，在 10 μM 的浓度下，两个 4 取代苯基噻唑具有中度细胞毒性。根据这些结果，苯基上的 4 取代似乎是细胞毒性的关键。然而，确切的电子和结构要求尚不清楚。

  DOI：

  10.1071/ch15461
• 作为产物：
  描述：

  (R)-2-(4-Nitro-phenyl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.55h， 生成 methyl 2-(4-nitrophenyl)thiazole-4-carboxylate
  参考文献：
  名称：

  由β-叠氮基二硫化物和羧酸或酸酐精确合成2,4-二取代噻唑：巯基噻唑C †的不对称合成

  摘要：

  提出了一种新颖有效的从羧酸或酸酐一锅合成2,4-二取代噻唑的方法。基于这种新方法，还提出了双-2,4-二取代的双（噻唑）天然产物巯基噻唑C的全合成。

  DOI：

  10.1039/c4ob01460j

文献信息

• Copper-catalyzed oxidation of azolines to azoles
  作者：Anna C. Dawsey、Vincent Li、Kimberly C. Hamilton、Jianmei Wang、Travis J. Williams

  DOI：10.1039/c2dt00025c

  日期：——

  We report herein convenient, aerobic conditions for the oxidation of thiazolines to thiazoles and data regarding the oxidation mechanism. These reactions feature operationally simple and environmentally benign conditions and proceed in good yield to afford the corresponding azoles, thus enabling the inexpensive preparation of valuable molecular building blocks. Incorporation of a novel diimine-ligated copper catalyst, [(MesDABMe)CuII(OH2)3]2+ [−OTf]2, provides increased reaction efficiency in many cases. In other cases copper-free conditions involving a stoichiometric quantity of base affords superior results.

  我们在此报告了便捷的厌氧条件下将噻唑啉氧化为噻唑的反应及其氧化机制的数据。这些反应具有操作简单和环保的特点，并且能以良好的产率生成相应的杂环化合物，从而实现价值分子构建块的廉价制备。引入一种新型的双亚胺配位铜催化剂[(MesDABMe)CuII(OH2)3]2+ [−OTf]2，在许多情况下提高了反应效率。而在其他情况下，使用计量的碱无铜条件能够获得更优的结果。
• Convenient Synthesis of Azolines to Azoles
  申请人：Williams Travis J.

  公开号：US20130012719A1

  公开（公告）日：2013-01-10

  Azolines are oxidized in the presence of a copper-containing catalyst to azoles in the presence of molecular oxygen. A synthetic scheme converting azolines azoles is also provided.

  在含有铜催化剂的情况下，吡唑烯被氧化为吡唑，同时存在分子氧。还提供了将吡唑烯转化为吡唑的合成方案。
• 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.
• The Synthesis and Biological Evaluation of Anithiactin A/Thiasporine C and Analogues
  作者：Richard A. Lamb、Michael P. Badart、Brooke E. Swaney、Sinan Gai、Sarah K. Baird、Bill C. Hawkins

  DOI：10.1071/ch15461

  日期：——

  The synthesis of anithiactin A has been achieved in four steps. Several closely related analogues were synthesised and their biological activity against colon and breast cancer cell lines evaluated. Anithiactin A was found not to be cytotoxic even at a high concentration (100 μM); however, two 4-substituted phenyl thiazoles were found to be moderately cytotoxic at 10 μM. Based on these results, 4-substitution on the phenyl group appears to be critical for cytotoxicity. However, the exact electronic and structural requirements are unclear.

  Anithiactin A 的合成分为四个步骤。合成了几种密切相关的类似物，并评估了它们对结肠癌和乳腺癌细胞系的生物活性。结果发现，即使在高浓度（100 μM）下，连翘素 A 也没有细胞毒性；但是，在 10 μM 的浓度下，两个 4 取代苯基噻唑具有中度细胞毒性。根据这些结果，苯基上的 4 取代似乎是细胞毒性的关键。然而，确切的电子和结构要求尚不清楚。