(2-acetylphenyl)carbamic acid ethyl ester | 6140-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-acetylphenyl)carbamic acid ethyl ester
• 英文别名: 2-ethoxycarbonylaminoacetophenone；ethyl N-(2-acetylphenyl)carbamate；ethyl (2-acetylphenyl)carbamate；(2-acetyl-phenyl)-carbamic acid ethyl ester；(2-Acetyl-phenyl)-carbamidsaeure-aethylester；2-Carbaethoxyamino-acetophenon
• CAS: 6140-13-2
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD09935136
• 分子量: 207.229
• InChiKey: NSJUTXFMYLBGSG-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  280.1±23.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 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：

  (2-acetylphenyl)carbamic acid ethyl ester 在 sodium hydroxide 、 sodium tetrahydroborate 、 溴 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.75h， 生成 2-氨基喹啉
  参考文献：
  名称：

  N- [2-（1-羟基-2-Y-乙基）苯基]氨基甲酸乙酯的基本介质行为（Y = SMe，SOMe，SO 2 Me，H，Br，CN）

  摘要：

  从一些共同结构为（2→tOOCNH-C6H4）-CHOH-CH2Y的硫代衍生物化合物的氨基甲酸酯基团的水解反应中获得的结果，提出了机理来解释产物，以及相对构型之间的关系。非对映异构体亚砜（Y = SOMe）与反应速率和立体化学结果。当进行其他氨基甲酸酯（Y = H，Br，CN）的水解反应时，还会产生其他有趣且出乎意料的产物。在当前情况下，氨基甲酸酯官能团的表现为非常通用的基团，能够轻松地转化为几种杂环。

  DOI：

  10.1016/0040-4020(89)80047-x
• 作为产物：
  描述：

  苯乙酮 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 potassium acetate 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 44.0h， 生成 (2-acetylphenyl)carbamic acid ethyl ester
  参考文献：
  名称：

  使用 2,2,2-三氯乙氧基羰基叠氮化物的羰基辅助铱催化 C-H 胺化

  摘要：

  使用 [Cp*Ir(III)Cl 2 ] 2作为催化剂和 2,2,2-三氯乙氧基羰基 (Troc) 叠氮化物作为胺化试剂，实现了芳烃的羰基定向单 C-H 胺化。多种芳基羰基化合物的胺化反应顺利进行，包括烷基和乙烯基芳基酮、仲和叔芳基酰胺以及乙酰基吲哚。所得邻-TrocNH 芳基羰基化合物很容易转化为相应的游离芳基胺、芳基氨基甲酸酯或芳基脲。利用邻位中 Troc 和羰基的亲电性质-TrocNH 芳基羰基化合物，随后用双亲核试剂环化也得到了证实。这为构建芳基稠合的N-杂环提供了一种有效的策略。

  DOI：

  10.1021/acs.joc.2c01636

文献信息

• [EN] CARBAMATE QUINABACTIN<br/>[FR] QUINABACTINE DE CARBAMATE
  申请人：UNIV CALIFORNIA

  公开号：WO2018017490A1

  公开（公告）日：2018-01-25

  The present invention relates to novel sulfonamide derivatives, to processes and intermediates for preparing them, to plant growth regulator compositions comprising them and to methods of using them for controlling the growth of plants, improving plant tolerance to abiotic stress (including environmental and chemical stresses), inhibiting seed germination and/or safening a plant against phytotoxic effects of chemicals.

  这项发明涉及新型磺胺基衍生物，涉及用于制备它们的工艺和中间体，涉及包含它们的植物生长调节剂组合物，以及使用它们控制植物生长、提高植物对非生物胁迫（包括环境和化学胁迫）的耐受性、抑制种子萌发和/或使植物对化学物质的毒害效应具有安全性的方法。
• Cyclic guanidines. IX. Synthesis of 2-amino-3,4-dihydroquinazolines as blood platelet aggregation inhibitors.
  作者：FUMIYOSHI ISHIKAWA、YOSHIFUMI WATANABE、JUNJI SAEGUSA

  DOI：10.1248/cpb.28.1357

  日期：——

  A series of aryl-or aralky-substituted 2-amino-3, 4-dihydroquinazolines and related compounds were synthesized. The compounds were evaluated for inhibitory activity towards collagen-and ADP-induced aggregation of rat blood platelet in vitro and ex vivo. A group of 3-benzyl-substituted derivatives had potent activity. The structure-activity relationships are discussed.

  合成了一系列含有苯基或苯甲基取代的2-氨基-3,4-二氢喹唑啉及其相关化合物。这些化合物在体外和体内对大鼠血小板胶原和ADP诱导的聚集具有抑制活性，其中一类3-苄基取代的衍生物表现出较强的活性。相关结构与活性的关系进行了探讨。
• Plant growth regulator compounds
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：US10791742B2

  公开（公告）日：2020-10-06

  The present invention relates to novel sulfonamide derivatives, to processes and intermediates for preparing them, to plant growth regulator compositions comprising them and to methods of using them for controlling the growth of plants, improving plant tolerance to abiotic stress (including environmental and chemical stresses), inhibiting seed germination and/or safening a plant against phytotoxic effects of chemicals.

  本发明涉及新型磺酰胺衍生物、制备磺酰胺衍生物的工艺和中间体、含有磺酰胺衍生物的植物生长调节剂组合物，以及使用磺酰胺衍生物控制植物生长、提高植物对非生物胁迫（包括环境和化学胁迫）的耐受性、抑制种子萌发和/或使植物免受化学品植物毒性影响的方法。
• 邻氨基芳基酮衍生物的合成方法
  申请人：南京大学

  公开号：CN115417796A

  公开（公告）日：2022-12-02

  本发明一种邻氨基芳基酮衍生物的合成方法，以银盐为催化剂，2,2,2‑三氯乙氧基羰基(Troc)叠氮化物为胺化试剂，实现芳烃的羰基定向单C‑H胺化，该方法提供了在温和条件下直接制备邻氨基芳基酮衍生物的方法，实现了多种芳基羰基化合物的胺化反应，包括烷基和乙烯基芳基酮、仲和叔芳基酰胺以及乙酰基吲哚。该方法可以利用所得邻位‑TrocNH芳基羰基化合物转化为相应的游离芳基胺、芳基氨基甲酸酯、芳基脲以及芳基稠合的N‑杂环。
• Searching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques
  作者：Ludmila E. Campos、Francisco M. Garibotto、Emilio Angelina、Jiri Kos、Tihomir Tomašič、Nace Zidar、Danijel Kikelj、Tomas Gonec、Pavlina Marvanova、Petr Mokry、Josef Jampilek、Sergio E. Alvarez、Ricardo D. Enriz

  DOI：10.1016/j.bioorg.2019.103125

  日期：2019.10

  The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specific BRAFi, have been clinically approved for the treatment of metastatic melanoma. Unfortunately, after the initial response, tumors become resistant and patients develop a progressive and lethal disease, making imperative the development of new therapeutic options. The main objective of this work was to find new BRAF inhibitors with different structural scaffolds than those of the known inhibitors. Our study was carried out in different stages; in the first step we performed a virtual screening that allowed us to identify potential new inhibitors. In the second step, we synthesized and tested the inhibitory activity of the novel compounds founded. Finally, we conducted a molecular modelling study that allowed us to understand interactions at the molecular level that stabilize the formation of the different molecular complexes.Our theoretical and experimental study allowed the identification of four new structural scaffolds, which could be used as starting structures for the design and development of new inhibitors of BRAF. Our experimental data indicate that the most active compounds reduced significantly ERK1/2 phosphorylation, a measure of BRAF inhibition, and cell viability. Thus, from our theoretical and experimental results, we propose new substituted hydroxynaphthalenecarboxamides, N-(hetero)aryl-piperazinylhydroxyalkylphenylcarbamates, substituted piperazinylethanols and substituted piperazinylpropandiols as initial structures for the development of new inhibitors for BRAF. Moreover, by performing QTAIM analysis, we are able to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analysis indicates which portion of the different molecules must be changed in order to obtain an increase in the binding affinity of these new ligands.