tert-butyl 2-(p-tolyl)-1H-pyrrole-1-carboxylate | 215187-25-0

• 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-(p-tolyl)-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 2-(4-methylphenyl)pyrrole-1-carboxylate
• CAS: 215187-25-0
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: OHCMNEPEILFJDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(p-tolyl)-1H-pyrrole-1-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-(4-tolyl)pyrrole
  参考文献：
  名称：

  Palladium(0)-Catalysed Arylations using Pyrrole and Indole 2-Boronic Acids

  摘要：

  以 N-(叔丁氧羰基)吡咯-2-硼酸或 N-(叔丁氧羰基)吲哚-2-硼酸作为铃木偶联的组分，介绍了 2-芳基吡咯和 2-芳基吲哚的多功能合成方法。

  DOI：

  10.1055/s-1998-1834
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 生成 tert-butyl 2-(p-tolyl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Transformation of the Non-Selective Aminocyclohexanol-Based Hsp90 Inhibitor into a Grp94-Seletive Scaffold

  摘要：

  Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan- inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests,similar to 440 nM affinity and >200-fold selectivity against cytosolic Hsp90 isoforms.

  DOI：

  10.1021/acschembio.6b00747

文献信息

• 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。
• Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight
  作者：Shiwei Zhang、Zhaocheng Tang、Wenhao Bao、Jia Li、Baodang Guo、Shuping Huang、Yan Zhang、Yijian Rao

  DOI：10.1039/c9ob00659a

  日期：——

  and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C–H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions

  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。
• Palladium(0)-Catalysed Arylations using Pyrrole and Indole 2-Boronic Acids
  作者：Christopher N. Johnson、Geoffrey Stemp、Neel Anand、Susanna C. Stephen、Timothy Gallagher

  DOI：10.1055/s-1998-1834

  日期：1998.9

  A versatile synthesis of 2-arylpyrroles and 2-arylindoles is described based on the use of either N-(Boc) pyrrole-2-boronic acid or N-(Boc) indole-2-boronic acid as components for Suzuki coupling.

  以 N-(叔丁氧羰基)吡咯-2-硼酸或 N-(叔丁氧羰基)吲哚-2-硼酸作为铃木偶联的组分，介绍了 2-芳基吡咯和 2-芳基吲哚的多功能合成方法。
• Synergism between few-layer black phosphorus and graphitic carbon nitride enhances the photoredox C–H arylation under visible light irradiation
  作者：Zafer Eroglu、Melek Sermin Ozer、Temirlan Kubanaliev、Haydar Kilic、Önder Metin

  DOI：10.1039/d2cy01090a

  日期：——

  synergistic effect at the heterojunction interfaces. As-prepared FLBP/g-CN heterojunctions were tested in photoredox C–H arylation of heteroarenes with diazonium salts under visible light irradiation and showed excellent activity, with the product yields reaching up to 94% under ambient conditions. The activity of FLBP/g-CN heterojunctions showed a volcano-shaped relation with respect to the BP loading

  太阳能驱动的化学转化的发展是最具吸引力的研究兴趣之一，因为它们为更可持续的未来奠定了基础。为了达到这个目标，应该设计和制造高效的光催化剂，特别是无金属光催化剂。为了设计具有光学、化学/热性能和长期稳定性的高效光催化剂，构建由地球丰富的元素组成的二维 (2D) 材料的异质结是最环保的选择之一。在这项研究中，通过结合少层黑磷（FLBP）和石墨氮化碳（g-CN）二元异质结，开发了一种高效的光氧化还原催化剂，在异质结界面处建立了协同效应。所制备的 FLBP/g-CN 异质结在可见光照射下用重氮盐对杂芳烃进行光氧化还原 C-H 芳基化测试，结果显示出优异的活性，在环境条件下产物收率高达 94%。FLBP/g-CN 异质结的活性与 BP 负载率呈火山型关系，其中 FLBP/g-CN 与 35 wt% FLBP 的性能最佳。FLBP/g-CN 异质结的底物范围在多种杂芳烃（呋喃、噻吩和 其中具有 35 wt%
• Transformation of the Non-Selective Aminocyclohexanol-Based Hsp90 Inhibitor into a Grp94-Seletive Scaffold
  作者：Sanket J. Mishra、Suman Ghosh、Andrew R. Stothert、Chad A. Dickey、Brian S. J. Blagg

  DOI：10.1021/acschembio.6b00747

  日期：2017.1.20

  Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan- inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests,similar to 440 nM affinity and >200-fold selectivity against cytosolic Hsp90 isoforms.