biphenyl-2-oxamic acid | 116490-13-2

• 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: biphenyl-2-oxamic acid
• 英文别名: 2-([1,1'-biphenyl]-2-ylamino)-2-oxoacetic acid；biphenyl-2-yl-oxalamic acid；Biphenyl-2-yl-oxalamidsaeure；Oxalsaeure-mono-(biphenylyl-(2)-amid)；Biphenylyl-(2)-oxamidsaeure；2-Oxo-2-(2-phenylanilino)acetic acid
• CAS: 116490-13-2
• 化学式: C₁₄H₁₁NO₃
• mdl: MFCD12069980
• 分子量: 241.246
• InChiKey: GISVFKAKOUIPMF-UHFFFAOYSA-N

物化性质

• 熔点：
  155-158 °C (decomp)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  biphenyl-2-oxamic acid 在 sodium persulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 以79.4%的产率得到6(5H)-菲啶酮
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Phenanthridinones from Biaryl-2-oxamic Acid under Radical Conditions

  摘要：

  Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products.

  DOI：

  10.1021/ol503459s
• 作为产物：
  描述：

  2-硝基联苯 在 tin(II) chloride dihdyrate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 biphenyl-2-oxamic acid
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Phenanthridinones from Biaryl-2-oxamic Acid under Radical Conditions

  摘要：

  Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products.

  DOI：

  10.1021/ol503459s

文献信息

• Decarboxylative Alkynylation of α-Keto Acids and Oxamic Acids in Aqueous Media
  作者：Hua Wang、Li−Na Guo、Shun Wang、Xin-Hua Duan

  DOI：10.1021/acs.orglett.5b01336

  日期：2015.6.19

  K2S2O8 promoted decarboxylative alkynylation of α-keto acids and oxamic acids has been developed. This process features mild reaction conditions, a broad substrate scope, and good functional-group tolerance, therefore providing a new and efficient access to a wide range of ynones and propiolamides. Furthermore, this radical process could also be successfully applied to alkynylation of the Csp2–H bond

  已经开发出温和的K 2 S 2 O 8促进α-酮酸和草酰胺酸的脱羧炔基化。该工艺具有温和的反应条件，广泛的底物范围和良好的官能团耐受性，因此提供了一种新型且有效的途径，可广泛使用炔酮和丙酰胺类化合物。此外，该自由基过程也可以成功地用于高价炔碘试剂对DMF中C sp 2 -H键的炔基化反应。
• First-in-Class Pan Caspase Inhibitor Developed for the Treatment of Liver Disease
  作者：Steven D. Linton、Teresa Aja、Robert A. Armstrong、Xu Bai、Long-Shiuh Chen、Ning Chen、Brett Ching、Patricia Contreras、Jose-Luis Diaz、Craig D. Fisher、Lawrence C. Fritz、Patricia Gladstone、Todd Groessl、Xin Gu、Julia Herrmann、Brad P. Hirakawa、Niel C. Hoglen、Kathy G. Jahangiri、Vincent J. Kalish、Donald S. Karanewsky、Lalitha Kodandapani、Joseph Krebs、Jeff McQuiston、Steven P. Meduna、Kip Nalley、Edward D. Robinson、Robert O. Sayers、Kristen Sebring、Alfred P. Spada、Robert J. Ternansky、Kevin J. Tomaselli、Brett R. Ullman、Karen L. Valentino、Suzanne Weeks、David Winn、Joe C. Wu、Pauline Yeo、Cheng-zhi Zhang

  DOI：10.1021/jm050307e

  日期：2005.11.1

  A series of oxamyl dipeptides were optimized for pan caspase inhibition, anti-apoptotic cellular activity and in vivo efficacy. This structure-activity relationship study focused on the P4 oxamides and warhead moieties. Primarily on the basis of in vitro data, inhibitors were selected for study in a murine model of alpha-Fas-induced liver injury. IDN-6556 (1) was further profiled in additional in vivo

  针对泛半胱天冬酶抑制，抗凋亡细胞活性和体内功效优化了一系列草酰二肽。这项结构-活性关系研究的重点是P4乙酰胺和弹头部分。主要根据体外数据，在α-Fas诱导的肝损伤小鼠模型中选择抑制剂进行研究。IDN-6556（1）在其他体内模型和药代动力学研究中得到了进一步的描述。现在，这种一流的胱天蛋白酶抑制剂已成为两项II期临床试验的主题，评估了其在肝病中使用的安全性和有效性。
• Application of High-Throughput Competition Experiments in the Development of Aspartate-Directed Site-Selective Modification of Tyrosine Residues in Peptides
  作者：Alex J. Chinn、Jaeyeon Hwang、Byoungmoo Kim、Craig A. Parish、Shane W. Krska、Scott J. Miller

  DOI：10.1021/acs.joc.0c01147

  日期：2020.7.17

  Herein we report a Cu-catalyzed, site-selective functionalization of peptides that employs an aspartic acid (Asp) as a native directing motif, which directs the site of O-arylation at a proximal tyrosine (Tyr) residue. Through a series of competition studies conducted in high-throughput reaction arrays, effective conditions were identified that gave high selectivity for the proximal Tyr in Asp-directed

  在本文中，我们报告了铜催化的肽的位点选择性官能化，该肽采用天冬氨酸（Asp）作为天然的导向基序，将O-芳基化位点导向近端酪氨酸（Tyr）残基。通过在高通量反应阵列中进行的一系列竞争研究，确定了在Asp定向的Tyr修饰中对Tyr近端具有高选择性的有效条件。在许多情况下，包括肽-小分子杂交体，在靠近Tyr残基的O-芳基化反应中都实现了良好的位点选择性。
• Efficient copper-catalyzed amination of DNA-conjugated aryl iodides under mild aqueous conditions
  作者：Yves Ruff、Frédéric Berst

  DOI：10.1039/c8md00185e

  日期：——

  Herein, we describe the development of copper-catalyzed cross-coupling of DNA-conjugated aryl iodides with aliphatic amines. This protocol leverages a novel ligand, 2-((2,6-dimethoxyphenyl)amino)-2-oxoacetic acid, to effect the transformation in aqueous DMSO, under mild conditions and in air, making it an ideal candidate for the synthesis of DNA-encoded libraries.

  在此，我们描述了铜催化 DNA 缀合的芳基碘化物与脂肪胺交叉偶联的发展。该方案利用新型配体 2-((2,6-二甲氧基苯基)氨基)-2-氧代乙酸，在温和条件下和空气中实现水性 DMSO 中的转化，使其成为 DNA 合成的理想候选者- 编码库。
• 29. Researches in the phenanthridine series. Part III. Mesosubstituted derivatives
  作者：Leslie P. Walls

  DOI：10.1039/jr9340000104

  日期：——