methyl 2-(4-chlorophenyl)thiazole-4-carboxylate | 1315510-11-2

• 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-chlorophenyl)thiazole-4-carboxylate
• 英文别名: methyl 2-(4-chlorophenyl)-1,3-thiazole-4-carboxylate
• CAS: 1315510-11-2
• 化学式: C₁₁H₈ClNO₂S
• mdl: MFCD17214759
• 分子量: 253.709
• InChiKey: ROGKOEIZDNPIQD-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±48.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-chlorophenyl)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91%的产率得到dimethyl 2,2'-di-(4-chlorophenyl)-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-chlorophenyl)-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 在 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(4-chlorophenyl)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。
• Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics
  作者：Waleed M. Hussein、Daniel Feder、Gerhard Schenk、Luke W. Guddat、Ross P. McGeary

  DOI：10.1016/j.ejmech.2018.08.004

  日期：2018.9

  obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ∼30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions

  紫色酸性磷酸酶（PAP）是在酸性条件下催化磷酸酯水解的金属酶。它们的活性位点在哺乳动物中包含Fe（III）Fe（II）金属中心，而在植物中包含Fe（III）Zn（II）或Fe（III）Mn（II）金属中心。在人类中，血清中PAP水平升高与骨质疏松症和代谢性骨恶性肿瘤的进展密切相关，这使PAP成为适合开发化学疗法以对抗骨疾病的靶标。由于难以获得人的酶，红芸豆和猪的相应酶以前已被用于开发特定的PAP抑制剂。在这里，对现有的先导化合物进行进一步的精制，以创建一系列具有K i的抑制剂。值低至约30μM。这些化合物对猪和红芸豆PAP的抑制常数具有可比的大小，表明相关的结合相互作用得以保留。与该系列中最有效的抑制剂化合物4f配合使用时，红芸豆PAP的晶体结构解析为2.40Å的分辨率。根据其竞争性抑制方式，该抑制剂可直接与活性位点的双核金属中心配位。对接模拟预测该化合物以相似的方式与人PAP结合。该研究
• Iron-catalyzed C(5)−H Imidation of Azole with <i>N</i> -Fluorobenzenesulfonimide
  作者：Xiaojiao Wang、Bowen Lei、Lifang Ma、Huixuan Jiao、Wenhua Xing、Jiaming Chen、Ziyuan Li

  DOI：10.1002/adsc.201701124

  日期：2017.12.19

  An iron(II)‐catalyzed direct imidation of oxazole and thiazole with N‐fluorobenzenesulfonimide (NFSI) through C(5)−H bond cleavage is disclosed, providing C5‐imidated azoles in moderate to excellent yields with broad substrate scope. This reaction represents the first iron‐catalyzed C−H imidation of arene where NFSI serves as the imidation reagent, and potentially constitutes an efficient access to

  公开了一种铁（II）催化的N-氟代苯磺酰亚胺（NFSI）通过C（5）-H键裂解的恶唑和噻唑直接酰亚胺化反应，可提供中等收率到优异收率的C5咪唑，具有广泛的底物范围。该反应代表了芳烃的第一个铁催化的CH酰亚胺化，其中NFSI用作酰亚胺化试剂，并潜在地构成了对C5官能化的唑的有效利用，具有重要的医学意义。
• 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.