N-(biphenylyl-2) oxamate de methyle | 127563-31-9

• 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: N-(biphenylyl-2) oxamate de methyle
• 英文别名: methyl 2-([1,1'-biphenyl]-2-ylamino)-2-oxoacetate；methyl 2-oxo-2-(2-phenylanilino)acetate
• CAS: 127563-31-9
• 化学式: C₁₅H₁₃NO₃
• mdl: MFCD26144690
• 分子量: 255.273
• InChiKey: SYHPWRDYWAISOY-UHFFFAOYSA-N

物化性质

• 熔点：
  85-88 °C
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(biphenylyl-2) oxamate de methyle 在 sodium persulfate 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 36.5h， 生成 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 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(biphenylyl-2) oxamate de methyle
  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

• Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
  作者：Fei Cheng、Tao Chen、Yin-Qiu Huang、Jia-Wei Li、Chen Zhou、Xiao Xiao、Fen-Er Chen

  DOI：10.1021/acs.orglett.1c03688

  日期：2022.1.14

  We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups

  我们开发了一种高效实用的铜催化交叉偶联，通过利用容易获得的芳基溴化物（或氯化物）和丙二酸盐直接构建多功能的 α-芳基酯。这些克级方法的周转率高达 1560，并且通过使用低催化剂负载、新的可用配体和绿色溶剂顺利进行。可以耐受多种官能团，并且使用 α-芳基酯来获得克级的非甾体抗炎药 (NSAID)。
• CuI/Oxalamide Catalyzed Couplings of (Hetero)aryl Chlorides and Phenols for Diaryl Ether Formation
  作者：Mengyang Fan、Wei Zhou、Yongwen Jiang、Dawei Ma

  DOI：10.1002/anie.201601035

  日期：2016.5.17

  Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N‐aryl‐N′‐alkyl‐substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N‐aryl‐N′‐alkyl‐substituted oxalamides are more effective ligands than bis(N‐aryl)‐substituted oxalamides. A wide range of electron‐rich and electron‐poor aryl and heteroaryl chlorides gave the corresponding

  CuI与N-芳基-N'-烷基取代的草酰胺配体结合可以有效地促进（杂）芳基氯与苯酚之间的偶联，使其在120°C下顺利进行。在此过程中，N-芳基-N'-烷基取代的草酰胺比双（N-芳基）-取代的草酰胺更有效。各种各样的富电子和贫电子的芳基和杂芳基氯化物都能以良好的收率得到相应的偶联产物。富电子酚和有限范围的贫电子酚实现了令人满意的转化。低至1.5 mol％的催化剂和配体负载量足以满足其中某些反应的放大规模。
• Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction
  作者：Patrick S. Fier、Kevin M. Maloney

  DOI：10.1021/acs.orglett.7b01403

  日期：2017.6.2

  modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

  模块化配体库的并行合成和质量导向纯化，高通量实验和合理的配体演化，已经导致了一种新型的铜催化剂，可用于合成具有无痕氢氧化物的苯酚。此处报道的温和的反应条件使许多复杂的类药物酚的后期合成成为可能。
• 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。