tert-butyl 2-(4-(ethoxycarbonyl)phenyl)-1H-pyrrole-1-carboxylate | 879904-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl 2-(4-(ethoxycarbonyl)phenyl)-1H-pyrrole-1-carboxylate
• 英文别名: 2-(4'-ethoxycarbonylphenyl)pyrrole-1-carboxylic acid tert-butyl ester；1,1-Dimethylethyl 2-[4-(ethoxycarbonyl)phenyl]-1H-pyrrole-1-carboxylate；tert-butyl 2-(4-ethoxycarbonylphenyl)pyrrole-1-carboxylate
• CAS: 879904-84-4
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: KPNMJNWHUAZFQP-UHFFFAOYSA-N

物化性质

• 沸点：
  439.9±47.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯佐卡因 在 Cercosporin 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 8.75h， 生成 tert-butyl 2-(4-(ethoxycarbonyl)phenyl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  ylene醌醌催化的光氧化还原活化作用，使（杂）芳烃与阳光直接芳基化

  摘要：

  天然存在的per醌类颜料（PQP）由于其出色的光敏性能而备受关注。作为光物理和光生物学的一个方面，它们已被广泛研究。然而，它们在光催化中的应用尚待探索。我们在这里报告说，阳光与1 mol％的头孢菌素（一种ylene醌类颜料之一）通过光氧化还原过程以良好的区域选择性和广泛的官能团相容性催化（杂）芳烃的直接C–H键芳基化。此外，即使通过含头孢菌素的上清液在液体发酵后不进行有机溶剂萃取和纯化的情况下，也实现了具有很大底物转化率的克级反应。

  DOI：

  10.1039/c9ob00659a

文献信息

• Metal-Free, Visible-Light-Mediated Direct C–H Arylation of Heteroarenes with Aryl Diazonium Salts
  作者：Durga Prasad Hari、Peter Schroll、Burkhard König

  DOI：10.1021/ja212099r

  日期：2012.2.15

  Visible light along with 1 mol % eosin Y catalyzes the direct C-H bond arylation of heteroarenes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and heteroarenes. The general and easy procedure provides a transition-metal-free alternative for the formation of aryl-heteroaryl bonds.

  可见光和 1 mol% 曙红 Y 通过光氧化还原过程催化杂芳烃与芳基重氮盐的直接 CH 键芳基化。我们研究了几种芳基重氮盐和杂芳烃的反应范围。通用且简单的程序为芳基-杂芳基键的形成提供了一种不含过渡金属的替代方法。
• C-H Arylation of <i>N</i> -Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins
  作者：Mukesh Kumar、Shweta Sharma、Parijat Sil、Manoj Kushwaha、Satyajit Mayor、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1002/ejoc.201900353

  日期：2019.6.16

  Herein, we have developed a metal‐free and mild condition for the synthesis of 2‐arylated heteroarenes. The complex forming property and charge transfer property of phenothiazine expanded its application towards catalysis The optimized condition has been successfully employed for the synthesis important marine natural product namely pentabromo/chloropseudilins (PBP/PCP). The synthesized Pentachloropseudilin

  在此，我们已经开发出了无金属的温和条件，可以合成2-芳基杂芳烃。吩噻嗪的复杂的形成性质和电荷转移性质将其扩展到催化领域。优化的条件已成功用于合成重要的海洋天然产物五溴/氯假单胞菌素（PBP / PCP）。合成的五氯伪尿素（PCP）已显示出Myosin1c耗竭效应的表型，这为将PCP用作细胞中Myosin 1功能的特异性探针提供了有力的依据。
• Palladium-Catalyzed Cross-Coupling Reactions of Heterocyclic Silanolates with Substituted Aryl Iodides and Bromides
  作者：Scott E. Denmark、John D. Baird

  DOI：10.1021/ol053165r

  日期：2006.2.1

  heterocyclic silanols undergo cross-coupling with a variety of aromatic iodides and bromides under mild conditions. In situ deprotonation of the silanols with an equivalent amount of sodium hydride in toluene generates the sodium salt that couples with iodides under the action of Pd(2)(dba)(3).CHCl(3) in good yield at room temperature to 50 degrees C. The aromatic bromides also couple with these salts

  [反应：见正文]在温和条件下，衍生自多种杂环硅烷醇的硅烷醇钠与各种芳族碘化物和溴化物发生交叉偶联。硅烷醇与甲苯中的等量氢化钠进行原位去质子化反应生成的钠盐在Pd（2）（dba）（3）.CHCl（3）的作用下与碘化物偶合，在室温至50的条件下产率很高芳族溴化物在Pd（I）催化剂12的作用下也与这些盐偶联。
• Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
  作者：Scott E. Denmark、John D. Baird、Christopher S. Regens

  DOI：10.1021/jo7023784

  日期：2008.2.1

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.