4-(methoxycarbonyl)phenyl N,N-diethylcarbamate | 1245824-30-9

• 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: 4-(methoxycarbonyl)phenyl N,N-diethylcarbamate
• 英文别名: methyl 4-((diethylcarbamoyl)oxy)benzoate；methyl 4-([diethylcarbamoyl]oxy)benzoate
• CAS: 1245824-30-9
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: XQKNSQTWMSXDHT-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±34.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(methoxycarbonyl)phenyl N,N-diethylcarbamate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以6.25 g的产率得到4-((diethylcarbamoyl)oxy)benzoic acid
  参考文献：
  名称：

  Di-aryl Sulfonamide Motif Adds π-Stacking Bulk in Negative Allosteric Modulators of the NMDA Receptor

  摘要：

  The N-methyl-D-aspartate receptor plays a critical role in central nervous system processes. Its diverse properties, as well as hypothesized role in neurological disease, render NMDA receptors a target of interest for the development of therapeutically relevant modulators. A number of subunit-selective modulators have been reported in the literature, one of which is TCN-201, a G1uN2A-selective negative allosteric modulator. Recently, it was determined from a cocrystallization study of TCN-201 with the NMDA receptor that a unique active pose exists in which the sulfonamide group of TCN-201 incorporates a pi-pi r stacking interaction between the two adjacent aryl rings that allows it to make important contacts with the protein. This finding led us to investigate whether this unique structural feature of the diaryl sulfonamide could be incorporated into other modulators that act on distinct pockets. To test whether this idea might have more general utility, we added an aryl ring plus the sulfonamide linker modification to a previously published series of G1uN2C- and G1uN2D-selective negative allosteric modulators that bind to an entirely different pocket. Herein, we report data suggesting that this structural modification of the NAB-14 series of modulators was tolerated and, in some instances, enhanced potency. These results suggest that this motif may be a reliable means for introducing a pi-pi stacking element to molecular scaffolds that could improve activity if it allowed access to ligand protein interactions not accessible from one planar aromatic group.

  DOI：

  10.1021/acsmedchemlett.8b00395
• 作为产物：
  描述：

  N,N-二乙基氯甲酰胺 、 对羟基苯甲酸甲酯 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.17h， 以27%的产率得到4-(methoxycarbonyl)phenyl N,N-diethylcarbamate
  参考文献：
  名称：

  镍催化芳基C–O亲电试剂与芳基新戊基乙二醇硼酸酯的交叉偶联

  摘要：

  在Ni-Na中首次比较了甲磺酸盐，氨基磺酸盐，酯，碳酸盐，氨基甲酸酯和甲基醚作为基于C-O的亲电子试剂的效率，这些亲电试剂连接到萘的1或2位以及活化和非活化的苯基底物上。催化与在对位含有富电子和缺电子取代基的新戊基硼硼酸苯基酯的交叉偶联。这些实验是在四种不同的基于Ni（II）和Ni（0）的催化剂的存在下进行的。基于Ni（II）的催化剂在K 3 PO 4介导大多数2-萘基C–O亲电试剂与芳基硼酸和新戊二醇硼酸酯的交叉偶联用作基础。当CsF用作碱时，相同的催化剂效率不高。然而，基于Ni（0）的催化剂表现出选择性效率，并且当具有反应性时，它们的效率高于同时存在K 3 PO 4和CsF的Ni（II）基催化剂的效率。这些结果既为交叉偶联提供了反应条件，又为各种基于C-O的亲电试剂与芳基新戊二醇硼酸酯的正交交叉偶联方法的完善提供了条件。除甲磺酸酯和氨基磺酸酯外，与芳基新戊基乙二醇硼酸酯交叉偶联时，所有

  DOI：

  10.1021/jo2022982

文献信息

• Copper <scp>porphyrin‐catalyzed</scp> C(sp ² ) <b>—</b> O bond construction via coupling phenols with formamides
  作者：Shuang Yang、Xiao‐Yan Chen、Ming‐Feng Xiong、Hao Zhang、Lei Shi、Dong‐Zi Lin、Hai‐Yang Liu

  DOI：10.1002/jccs.202100046

  日期：2021.8

  construction of C(sp2)—O bond via coupling formamides with phenols was achieved firstly. A broad range of substrates afforded various carbamates in moderate to good yields with good functional group tolerance at low catalyst loading. Intermolecular competing kinetic isotope effect experiment indicated that the generation of formamide radical is the rate-determining step of current cross-dehydrogenative coupling

  首次实现了铜卟啉催化甲酰胺与酚类偶联构建C(sp 2 )-O键。广泛的底物以中等至良好的产率提供各种氨基甲酸酯，在低催化剂负载下具有良好的官能团耐受性。分子间竞争动力学同位素效应实验表明，甲酰胺自由基的产生是当前交叉脱氢偶联（CDC）反应的定速步骤。该研究拓展了金属卟啉在CDC反应中的应用。
• A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant
  作者：Wenfang Xiong、Chaorong Qi、Tianzuo Guo、Min Zhang、Kai Chen、Huanfeng Jiang

  DOI：10.1039/c6gc03465a

  日期：——

  A Cu-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide is described, providing a route to O-aryl carbamates.

  描述了芳基硼酸，胺和二氧化碳的Cu催化的氧化偶联反应，提供了制备O-芳基氨基甲酸酯的途径。
• Ruthenium-Catalyzed Selective Aerobic Oxidative<i>ortho</i>-Alkenylation of Substituted Phenols with Alkenes through C-H Bond Activation
  作者：Mallu Chenna Reddy、Masilamani Jeganmohan

  DOI：10.1002/ejoc.201201463

  日期：2013.2

  The oxidative coupling of phenyl carbamates and acetates with alkenes in the presence of a catalytic amount of [RuCl2(p-cymene)]2, AgSbF6, and Cu(OAc)2·H2O under air provided substituted alkene derivatives in a highly regio- and stereoselective manner. The catalytic reaction was compatible with various alkenes such as acrylates, vinyl sulfones, acrylonitrile, and substituted styrenes. The present catalytic

  在催化量的 [RuCl2(p-cymene)]2、AgSbF6 和 Cu(OAc)2·H2O 存在下，苯基氨基甲酸酯和乙酸酯与烯烃的氧化偶联在空气中提供了高度区域和立体选择性方式。催化反应与各种烯烃相容，如丙烯酸酯、乙烯基砜、丙烯腈和取代苯乙烯。本催化反应还与芳香环上具有各种富电子、缺电子和卤素取代基的氨基甲酸苯酯和乙酸酯相容。用取代的乙酸苯酯进一步检查催化反应。以LiOH· 或K2CO3为碱，取代的烯烃衍生物转化为相应的苯酚衍生物。为了说明催化反应，
• Photochemically Driven Nickel‐Catalyzed Carboxylative C−N Coupling: Scope and Mechanism**
  作者：Seifallah Abid、Kevin P. Quirion、Yi Yang、Renhe Tang、Binh Khanh Mai、Peng Liu、Anis Tlili

  DOI：10.1002/chem.202301271

  日期：2023.8.4

  The carboxylative Buchwald–Hartwig amination is disclosed herein under mild conditions of temperature and under atmospheric pressure of CO2. The key to success is the use of a dual strategy organophotocatalysis/nickel catalysis under visible light irradiation. The developed conditions demonstrated high functional group tolerance toward (hetero)aryl iodide and bromide. Furthermore, preliminary mechanistic

  本文公开了在温和的温度条件和CO 2大气压下的羧化Buchwald-Hartwig胺化。成功的关键是在可见光照射下使用有机光催化/镍催化双重策略。所开发的条件表现出对（杂）芳基碘化物和溴化物的高官能团耐受性。此外，包括化学计量反应和 DFT 计算在内的初步机理研究揭示了反应机理。
• Directed Ortho Borylation of Phenol Derivatives Catalyzed by a Silica-Supported Iridium Complex
  作者：Kenji Yamazaki、Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol101493m

  日期：2010.9.17

  The directed ortho borylation of phenol derivatives protected with an N,N-diethylcarbamoyl group was efficiently catalyzed by an immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine. The utility of the carbamoyloxy group as a leaving group for metal-catalyzed cross-coupling reactions was demonstrated by its utilization in the synthesis of a terphenyl derivative.