2-苄基-4-苯基-4H-1,3-恶唑-5-酮 | 60050-57-9

• 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-苯基-4H-1,3-恶唑-5-酮
• 英文名称: 2-benzyl-4-phenyl-4H-oxazolin-5-one
• 英文别名: 2-Benzyl-4-phenyl-2-oxazolin-5-on；2-benzyl-4-phenyl-4H-oxazol-5-one；5(4H)-Oxazolone, 4-phenyl-2-(phenylmethyl)-；2-benzyl-4-phenyl-4H-1,3-oxazol-5-one
• CAS: 60050-57-9
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: CJGCTZPHUXFSCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-苯基-4H-1,3-恶唑-5-酮 在 劳森试剂 作用下， 以 氯苯 为溶剂， 以51 %的产率得到2-benzyl-4-phenyl-thiazole
  参考文献：
  名称：

  Lawesson 试剂促进吖内酯脱氧合成 2,4-二取代噻唑

  摘要：

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。

  DOI：

  10.1039/d2ob01939f
• 作为产物：
  描述：

  methyl 2-((diphenylmethylene)amino)-2-phenylacetate 在 盐酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 2-苄基-4-苯基-4H-1,3-恶唑-5-酮
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524

文献信息

• 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。
• 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。
• Regioselective Synthesis of Tetrasubstituted Pyrroles by 1,3-Dipolar Cycloaddition and Spontaneous Decarboxylation
  作者：Yongju Kim、Jonghoon Kim、Seung Bum Park

  DOI：10.1021/ol8022193

  日期：2009.1.1

  We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2h)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
• WO2007/133790
  申请人：——

  公开号：——

  公开（公告）日：——