4-苯基-1,3-二氢-2H-咪唑-2-酮 | 6794-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-苯基-1,3-二氢-2H-咪唑-2-酮
• 中文别名: 4-苯基-1,3-二氢-咪唑-2-酮
• 英文名称: 4-phenyl-1,3-dihydro-imidazol-2-one
• 英文别名: 4-phenyl-1,3-dihydro-2H-imidazol-2-one；4-phenyl-1,3-dihydroimidazol-2-one
• CAS: 6794-69-0
• 化学式: C₉H₈N₂O
• mdl: MFCD00518909
• 分子量: 160.175
• InChiKey: JUCLXFPLJNDBJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  4-苯基-1,3-二氢-2H-咪唑-2-酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 5-Phenyl-1-propyl-1,3-dihydro-imidazol-2-one
  参考文献：
  名称：

  Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives

  摘要：

  Methods for selectively protecting one of the degenerate nitrogen atoms of the cyclic urea derivatives 1,3-dihydro-2H-benzimidazol-2-one (6a), 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (11), 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-ones (20), 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (22), and 1,3-dihydro-4-phenyl-2H-imidazol-2-one (27) were developed. Heating these cyclic ureas with ethyl 2-pyridyl carbonate in the presence of a base in CH3CN at reflux or DMF at 100 degrees C cleanly provided the monoethoxycarbonyl derivatives 7a, 12, 21, 23, and 28, respectively. Alternatively, treatment of 6a with an excess of diethyl pyrocarbonate or di-tert-butyl dicarbonate afforded the bis-alkoxycarbonyl derivatives 8a and 8b, respectively, which underwent disproportionation to 7a and 7b upon heating with 1 mol equiv of 6a and K2CO3 in CH3CN at reflux. The regiochemistry of the introduction of alkoxycarbonyl groups to benzimidazol-2-one derivatives was not significantly influenced by an electron-withdrawing (CF3, 6b) or an electron-donating (OCH3, 6c) substituent at C-5 of the heterocyclic ring. However, the reaction was found to be sensitive to steric factors since a chlorine substituent ortho to one of the urea N atoms (6e) completely directed the alkoxycarbonyl moiety to the less sterically encumbered N atom, affording a single product (7f, 7g). Alkylation of 7a-g proceeded efficiently to provide products 10a-10ag after removal of the protecting group. Halogenation of monoprotected benzimidazol-2-one 7a occurred regiospecifically to give the monohalo derivatives 7h, 7i, and 7k, the identity of which were readily established from the characteristic chemical shift and spin coupling pattern in their 1H NMR spectra. A protecting group interchange strategy that took advantage of the distinctive chemical reactivities of the EtO(2)C and t-BuO(2)C protecting groups toward isopropylamine was developed that provided access to the isomerically substituted series of monohalo, mono-N-alkylated benzimidazol-2-ones 71 and 7m. The efficient derivatization of the unprotected N atom of these monoprotected cyclic urea derivatives was accomplished by treating with activated and unactivated halides in the. presence of K2CO3 or exposure to alcohols under Mitsunobu conditions. In several cases, mixtures of O- and N-alkylated products were produced which were readily separated by chromatography. Alkylation of 7h with activated halides, using K2CO3 in CH3CN at reflux, occurred without protecting group equilibration; however, a mixture of isomeric alkylated products was obtained when 7h was heated at 110 degrees C in DMF with cyclohexylmethyl bromide in the presence of K2CO3 as the base. Derivatization of 7h under Mitsunobu reaction conditions proceeded with retention of the topological substituent relationships. Subsequent removal of the alkoxycarbonyl moiety afforded monoalkylated cyclic urea derivatives.

  DOI：

  10.1021/jo00111a014
• 作为产物：
  描述：

  5-苯基海因 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 4-苯基-1,3-二氢-2H-咪唑-2-酮
  参考文献：
  名称：

  THE ACTION OF LITHIUM ALUMINUM HYDRIDE ON 3-METHYL-5-PHENYLHYDANTOIN AND 5-PHENYLHYDANTOIN

  摘要：

  DOI：

  10.1021/jo01151a017

文献信息

• [EN] QUINAZOLINONE COMPOUNDS AND DERIVATIVES THEREOF<br/>[FR] COMPOSÉS QUINAZOLINONES ET LEURS DÉRIVÉS
  申请人：AMGEN INC

  公开号：WO2014036022A1

  公开（公告）日：2014-03-06

  Compounds of Formula I are useful inhibitors of tankyrase. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物是坦克酶的有用抑制剂。公式I的化合物具有以下结构：其中变量的定义在此提供。
• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Cu ^I ‐Catalyzed Sequential Diamination and Dehydrogenation of Terminal Olefins: A Facile Approach to Imidazolinones
  作者：Yingguang Zhu、Yian Shi

  DOI：10.1002/chem.201404381

  日期：2014.10.20

  Diamination of olefins presents a powerful strategy to access vicinal diamines. During the last decade, metal‐catalyzed diamination of olefins has received considerable attention. This study describes an efficient sequential diamination and dehydrogenation process of terminal olefins with CuBr as catalyst and di‐tert‐butyldiaziridinone as nitrogen source, providing a facile and viable approach to a

  烯烃的二胺化提供了一种获得邻位二胺的强大策略。在过去的十年中，金属催化的烯烃二胺化受到了相当多的关注。本研究描述了一种以 CuBr 为催化剂、二叔丁基二氮杂环丙烷酮为氮源的末端烯烃的高效连续二胺化和脱氢过程，为各种咪唑啉-2-酮提供了一种简便可行的方法，这些咪唑啉-2-酮是存在于石墨烯中的重要结构基序。各种生物活性分子。
• Phenacyl esters of acetic acid derivatives and their application for the synthesis of 2-oxo-4-phenyl-5-(phenylhydrazono)-2,5-dihydro-furan-3-derivatives
  作者：Jan Hlaváč、Pavel Hradil、Radek Mělnický、Lubomír Kvapil、Petr Šlézar、Martin Grepl--、Pavel Hradil、Antonín Lyčka、Martin Grepl

  DOI：10.1002/jhet.5570450529

  日期：2008.9

  Coupling of various substituted phenacyl acetates 1 and diazonium salts 3 was studied. If the phenacyl acetates were substituted by an electronaceptor group such as CN or COOEt 3-substituted phenyl-5-(phenyl-hydrazono)-5H-furan-2-ones 4 were formed. Also synthesis of aza and diaza analogs is described. The compounds were characterized using MS and NMR spectroscopy.

  研究了各种取代的乙酸苯甲酰乙酸酯1和重氮盐3的偶联。如果苯甲酰甲基乙酸盐是由一个electronaceptor基团如CN或COOEt烷基取代的3-取代的苯基-5-（苯基-亚肼基）-5- ħ -呋喃-2-酮4形成。还描述了氮杂和二氮杂类似物的合成。使用MS和NMR光谱对化合物进行表征。
• [EN] CYCLIC N-CARBOXAMIDE COMPOUNDS USEFUL AS HERBICIDES<br/>[FR] COMPOSÉS CYCLIQUES N-CARBOXAMIDE UTILES EN TANT QU'HERBICIDES
  申请人：DU PONT

  公开号：WO2017023515A1

  公开（公告）日：2017-02-09

  Disclosed are compounds of Formula (1), including all stereoisomers, N-oxides, and salts thereof, (Formula (1)) wherein G, J, Q1, R4, Y2, Q2, R5 and Y1 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

  本发明涉及公式（1）的化合物，包括所有立体异构体、N-氧化物和盐，（公式（1））其中G、J、Q1、R4、Y2、Q2、R5和Y1如本说明所定义。本发明还涉及包含公式（1）化合物的组合物以及控制不良植被的方法，其包括将本发明的化合物或组合物与不良植被或其环境接触，以有效量控制不良植被的生长。