methyl (2-acetylphenyl)carbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-acetylphenyl)carbamate
• 英文别名: methyl N-(2-acetylphenyl)carbamate
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: KZQZEFLRCLDSPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  methyl (2-acetylphenyl)carbamate 在 盐酸 、 氢溴酸 、 二甲基亚砜 作用下， 以 水 、 乙酸乙酯 为溶剂， 以70 %的产率得到methyl [2-(2-bromo-2-chloroacetyl)phenyl]carbamate
  参考文献：
  名称：

  新型氨基甲酸酯苯乙酮衍生物的合成及一些转化

  摘要：

  摘要 苯基氨基甲酸甲酯、2-(吗啉-4-基)乙基苯基氨基甲酸酯和 2-(吡啶-2-基)乙基苯基氨基甲酸酯与乙酸酐在多聚磷酸中于 50–55°C (3 h) 的酰化涉及对位关于氨基甲酸酯基团，形成相应的苯乙酮。2-甲氧基苯基氨基甲酸甲酯在类似条件下被酰化，得到 5-乙酰基-2-甲氧基苯基氨基甲酸甲酯。4-和 2-乙酰苯基氨基甲酸甲酯与N反应-溴代琥珀酰亚胺在醋酸铜 (II) 和 DMF 存在下于 80°C 和在 DMSO 存在下在乙酸乙酯中于 30–33°C 与 HCl 和 HBr 反应得到甲基 [4(2)-(2-二甲氨基- 2-oxoacetyl)phenyl]氨基甲酸酯和[4(2)-(2-bromo-2-chloroacetyl)phenyl]氨基甲酸甲酯。2-(morpholin-4-yl) 乙基和 2-(pyridin-2-yl) 乙基 (4-acetylphenyl) 氨基甲酸酯与

  DOI：

  10.1134/s1070428023010062
• 作为产物：
  描述：

  邻硝基苯乙酮 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl (2-acetylphenyl)carbamate
  参考文献：
  名称：

  微波辅助合成的取代3,4-二氢喹唑啉酮†

  摘要：

  报道了一种微波辅助的多组分方案，该方案通过新颖的级联亚胺/环化/氮杂-亨利反应序列合成取代的3,4-二氢喹唑啉酮。从氨基甲酸邻甲酰基酯开始，通过环状亚胺鎓离子中间体以中等至优异的产率合成了一系列结构多样的3,4-二氢喹唑啉酮。值得注意的是，该反应是快速，灵活，易于执行并且耐受各种官能团的。

  DOI：

  10.1039/c4ob02417f

文献信息

• An Electrochemical Route for Special Oxidative Ring‐Opening of Indoles
  作者：Hong Qin、Zhao Yang、Zhen Zhang、Chengkou Liu、Wei He、Zheng Fang、Kai Guo

  DOI：10.1002/chem.202101527

  日期：2021.9.9

  A novel electrochemical protocol for the oxidative cleavage of indoles has been developed, which offers a simple way to access synthetically useful anthranilic acid derivatives. In undivided cells, a wide variety of indoles and alcohol compounds are examined to afford amide ester aromatics without using extra oxidants and stoichiometric metal catalysts, which avoids the formation of undesired by-products

  已经开发了一种用于吲哚氧化裂解的新型电化学方案，它提供了一种获得合成有用的邻氨基苯甲酸衍生物的简单方法。在未分割的电池中，研究了多种吲哚和醇化合物以提供酰胺酯芳烃，而无需使用额外的氧化剂和化学计量金属催化剂，这避免了不需要的副产物的形成并表现出高原子经济性。我们在这个角度描述的产品代表了众多药物分子和工业化学试剂的合成中间体，并且在未来具有显着的潜在应用。
• [EN] 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE COMPOUNDS FOR THE TREATMENT OF TUBERCULOSIS<br/>[FR] COMPOSES 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2005042542A1

  公开（公告）日：2005-05-12

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1)in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and -(CH2)nR2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30)and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下一般式表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物：(1)在上述式(1)中，R1代表氢原子或C1-C6烷基，n代表0至6的整数，R1和-(CH2)nR2可以与下面的式(30)一起形成一个螺环，与相邻的碳原子一起（在下面的式中，RRR代表可能在哌啶环上具有取代基的哌啶基），(30)和R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似物。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型耐酸细菌具有出色的杀菌作用。
• 2,3-Dihydro-6-Nitroimidazo (2,1-b) Oxazole Compounds for the Treatment of Tuberculosis
  申请人：Tsubouchi Hidetsugu

  公开号：US20080119478A1

  公开（公告）日：2008-05-22

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1) in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and —(CH2) n R2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30) and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种由下述通式（1）表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物： 在上述式（1）中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R1和—(CH2)nR2可以与相邻的碳原子形成如下式（30）所示的螺环，其中，在下式中，RRR代表可能在哌啶环上具有取代基的哌啶基： （30）且R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似基团。该化合物对结核分枝杆菌、多重耐药结核分枝杆菌和非典型酸杆菌具有优异的杀菌作用。
• Synthesis of New Functionally Substituted Aryl- and Hetarylcarbamates Based on Ninhydrin
  作者：A. V. Velikorodov、A. S. Zukhairaeva、A. K. Chabakova、V. B. Kovalev

  DOI：10.1134/s1070428018100123

  日期：2018.10

  The condensation of methyl (ethyl) phenylcarbamates with ninhydrin in concentrated sulfuric acid gave dialkyl [1,3-dioxoindan-2,2-diyldi(4,1-phenylene)]biscarbamates. Treatment of the latter with hydrazine hydrate resulted in the transformation of the indandione fragment into phthalazinone. Ninhydrin reacted with methyl (hydroxyphenyl)carbamates in glacial acetic acid to produce dihydroxy derivative of oxotrihydroindeno[ 1,2-b][1]benzofuran possessing a carbamate group. Tandem reaction of ninhydrin with methyl (acetylphenyl) carbamates on heating in boiling glacial acetic acid, followed by addition of hydrazine hydrate in acetonitrile, afforded methyl (5-oxo-5H-indeno[1,2-c]pyridazin-3-yl)phenylcarbamates.
• An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents
  作者：Mónica Carril、Raul SanMartin、Fátima Churruca、Imanol Tellitu、Esther Domínguez

  DOI：10.1021/ol051291p

  日期：2005.10.1

  [GRAPHICS]A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2'-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular alpha-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.