2-苄基-4-甲基-4H-1,3-恶唑-5-酮 | 58482-85-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-苄基-4-甲基-4H-1,3-恶唑-5-酮
• 英文名称: 2-benzyl-4-methyl-4H-oxazolin-5-one
• 英文别名: 5(4H)-Oxazolone, 4-methyl-2-(phenylmethyl)-；2-benzyl-4-methyl-4H-1,3-oxazol-5-one
• CAS: 58482-85-2
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: MPRJDQMHTHKAKE-UHFFFAOYSA-N

物化性质

• 沸点：
  104-106 °C(Press: 0.06 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苄基-4-甲基-4H-1,3-恶唑-5-酮 在 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 3-benzyl-1,3a,4,5,6,6a-hexahydro-1-methyl-4,6-dioxo-5-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted Δ-Pyrrolines:  exo-Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones

  摘要：

  We report herein a silver(I)-catalyzed exo-selective synthesis of highly substituted Delta1-pyrroline scaffolds from amino acid-derived münchnones. Silver acetate successfully catalyzed the cycloaddition reaction of azlactones with alkenes, generating Delta1-pyrrolines in very good yields without isomerization to the Delta2-pyrrolines or decarboxylation.

  DOI：

  10.1021/ja046149i
• 作为产物：
  描述：

  2-benzylidene-4-methyl-2H-oxazol-5-one 在 镍 、 乙酸乙酯 作用下， 生成 2-苄基-4-甲基-4H-1,3-恶唑-5-酮
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯甲酰-DL-苯丙氨酸 在 2-苄基-4-甲基-4H-1,3-恶唑-5-酮 、 氯仿 作用下， 生成 4-苄基-2-苯基-2-噁唑啉-5-酮
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：

文献信息

• Diazabutadienes in heterocyclic syntheses. Preparation of pyrimidin-6-ones by reaction of 4-dialkylamino-1,3-diaza-1,3-butadienes with 2-oxazolin-5-ones
  作者：Bir Sain、Satyendra P. Singh、Jagir S. Sandhu

  DOI：10.1016/s0040-4020(01)81230-8

  日期：1992.1

  1-aryl-4-dimethylamino-2-methylthio-1,3-diaza-1,3-butadienes ( reacted with 2-oxazolin-5-ones () to yield pyrimidin-6-ones () and () respectively as single diastereoisomers with reverse stereochemistry. Reaction of 1,2-diphenyl-4-methylthio-4-amino-1,3-diaza-1,3-butadienes () with () also yielded pyrimidin-6-ones ().

  1-芳基-4-二甲基氨基-2-苯基-1,3-二氮杂-1,3-丁二烯（和1-芳基-4-二甲基氨基-2-甲硫基-1,3-二氮杂-1,3-丁二烯（已反应与2-恶唑啉-5-酮（）分别生成具有相反立体化学特征的单一非对映异构体的嘧啶-6-酮（）和（）1，2-二苯基-4-甲硫基-4-氨基-1,3-的反应diaza-1,3-butadienes（）与（）也可生成嘧啶6-one（）。
• NF-kB inhibitors and uses threreof
  申请人：Board of Trustees of MICHIGAN STATE UNIVERSITY

  公开号：US20030232998A1

  公开（公告）日：2003-12-18

  A new class of imidazolines as 4-position acids or esters with very potent anti-inflammatory as well as antimicrobial activity is described. The synthesis of these imidazolines includes a multicomponent reaction applicable to a combinatorial synthetic approach. The combination of these two key characteristics provides an effective therapeutic drug in the treatment of septic shock as well as many other inflammatory (arthritis and asthma) and infectious disorders. The use of this novel class of non-steroidal agents as anti-inflammatory agents (for the treatment of asthma, etc.), antibacterial agents, and antiseptic agents is described. The compounds are also useful in the treatment of tumors (such as cancers). The imidazolines are potent inhibitors of the transcription factor NF-&kgr;B as well as potent activity against the Gram (+) bacterium. The compositions are also useful for treating autoimmune diseases and for inhibiting rejection of organ and tissue transplants.

  描述了一类新型的咪唑啉化合物，作为4-位置酸或酯具有非常强大的抗炎和抗菌活性。这些咪唑啉的合成包括一种适用于组合合成方法的多组分反应。这两个关键特性的结合提供了一种有效的治疗药物，可用于治疗败血症休克以及许多其他炎症（如关节炎和哮喘）和传染性疾病。描述了这一新型非甾体类抗炎药物（用于治疗哮喘等）、抗菌药物和防腐剂的用途。这些化合物还可用于治疗肿瘤（如癌症）。咪唑啉是转录因子NF-κB的强效抑制剂，对革兰氏阳性细菌也具有强效活性。这些组合物还可用于治疗自身免疫性疾病，并抑制器官和组织移植的排斥。
• Potassium Acetate-Catalyzed Double Decarboxylative Transannulation To Access Highly Functionalized Pyrroles
  作者：Jun-Kuan Li、Biying Zhou、Yu-Chen Tian、Chunman Jia、Xiao-Song Xue、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1021/acs.orglett.0c03621

  日期：2020.12.18

  remodeling by utilizing CO2 moiety as traceless activating and directing groups in both reaction partners. The synthetic value is evidenced by the rapid preparation of a broad spectrum of highly functionalized 3-carbamoyl-4-aryl pyrroles in good to excellent yields with exclusive regio-control, including the important Atorvastatin core.

  有效构建通用吡咯药物核心的新合成策略的开发，尤其是在操作上简单且对环境无害的方式，仍然是一个艰巨而具有挑战性的目标。在这里，我们报告了易于获得的恶唑酮和异恶唑烷二酮之间的KOAc催化的双脱羧环过氧化物。这种转化代表了利用CO 2部分作为两个反应伙伴中无痕的活化和引导基团进行骨骼重塑的新方法。合成的价值可通过快速制备各种高官能度的3-氨基甲酰基-4-芳基吡咯，以良好的收率，并通过独家区域控制（包括重要的阿托伐他汀核心）来获得。
• Multicomponent Synthesisof Highly Substituted Imidazolines via a Silicon Mediated 1,3-DipolarCycloaddition
  作者：J. J. Tepe、S. Peddibhotla

  DOI：10.1055/s-2003-40196

  日期：——

  multicomponent synthesis of highly functionalized imidazolines is reported. A silicon mediated 1,3 dipolar cycloaddition of the in situ generated munchnone with an imine resulted in the formation ofhighly substituted imidazolines. The imidazolines contain a four-point diversity and two stereocenters and the cycloaddition reaction is applicable to aryl, alkyl, acyl, and heterocyclic substitutions.

  报道了高度官能化咪唑啉的非对映选择性多组分合成。硅介导的 1,3 偶极环加成原位产生的 munchnone 与亚胺导致形成高度取代的咪唑啉。咪唑啉具有四点多样性和两个立体中心，环加成反应适用于芳基、烷基、酰基和杂环取代。
• NF-kappaB inhibitors and uses thereof
  申请人：Tepe J. Jetze

  公开号：US20050020586A1

  公开（公告）日：2005-01-27

  A new class of imidazolines as 4-position esters with very potent anti-inflammatory as well as antimicrobial activity is described. The synthesis of these imidazolines includes a multicomponent reaction applicable to a combinatorial synthetic approach. The combination of these two key characteristics provides an effective therapeutic drug in the treatment of septic shock as well as many other inflammatory (arthritis and asthma) and infectious disorders. The use of this novel class of non-steroidal agents as anti-inflammatory agents (for the treatment of asthma, etc.), antibacterial agents, and antiseptic agents is described. The compounds are also useful in the treatment of tumors (such as cancers). The imidazolines are potent inhibitors of the transcription factor NF-kB as well as potent activity against the Gram (+) bacterium. The compositions are also useful for treating autoimmune diseases and for inhibiting rejection of organ and tissue transplants.

  描述了一类新型的4-位置酯基咪唑啉类化合物，具有非常强效的抗炎和抗微生物活性。这些咪唑啉类化合物的合成包括一种适用于组合合成方法的多组分反应。这两种关键特性的结合提供了一种有效的治疗药物，可用于治疗脓毒性休克以及许多其他炎症性（如关节炎和哮喘）和传染性疾病。描述了这种新型的非甾体类药物作为抗炎药物（用于治疗哮喘等）、抗菌药物和防腐剂的用途。这些化合物还可用于治疗肿瘤（如癌症）。这些咪唑啉类化合物是转录因子NF-kB的有效抑制剂，对革兰氏阳性细菌也具有强效活性。这些化合物还可用于治疗自身免疫性疾病以及抑制器官和组织移植的排斥反应。