2-methyl-4-methyl-4H-oxazolin-5-one | 69773-71-3

• 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
• 英文名称: 2-methyl-4-methyl-4H-oxazolin-5-one
• 英文别名: 2,4-dimethyl-2-oxazolin-5-one；2,4-dimethyloxazol-5(4H)-one；4-dimethyl-4H-oxazolin-5-one；2,4-dimethyloxazolin-5-one；2,4-dimethyl-4H-oxazol-5-one；2,4-dimethyl-4H-oxazolin-5-one；2,4-dimethyl-4H-1,3-oxazol-5-one
• CAS: 69773-71-3
• 化学式: C₅H₇NO₂
• 分子量: 113.116
• InChiKey: RJUMBKYAQIKACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-methyl-4-methyl-4H-oxazolin-5-one 在 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 1,3a,4,5,6,6a-hexahydro-1,3-dimethyl-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：

  N-乙酰-DL-丙氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-methyl-4-methyl-4H-oxazolin-5-one
  参考文献：
  名称：

  Diastereochemical Diversity of Imidazoline Scaffolds via Substrate Controlled TMSCl Mediated Cycloaddition of Azlactones

  摘要：

  We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.

  DOI：

  10.1021/ol052118w

文献信息

• [8+2] Formal Cycloaddition Reactions of Tropones with Azlactones under Brønsted Acid Catalysis and Synthesis of α-(2-Tropyl), α-Alkyl α-Amino Acids
  作者：Francisco Esteban、Ricardo Alfaro、Francisco Yuste、Alejandro Parra、José Luis García Ruano、José Alemán

  DOI：10.1002/ejoc.201301774

  日期：2014.3

  The reaction of tropones with azlactones catalyzed by Bronsted acids affords a variety of dihydro-2H-cyclohepta[b]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can easily be opened by nucleophiles to afford a new type of α,α-disubstituted α-amino acid (or peptide) containing seven-membered rings at the quaternary position.

  由布朗斯台德酸催化的托酮与吖内酯的反应提供了多种二氢-2H-环庚 [b] 呋喃衍生物，对应于正式的 [8+2] 环加成过程。它们可以很容易地被亲核试剂打开，以提供一种新型的 α,α-二取代 α-氨基酸（或肽），在四元位置含有七元环。
• Gold(I)-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition and Mannich Reactions of Azlactones
  作者：Asa D. Melhado、Giovanni W. Amarante、Z. Jane Wang、Marco Luparia、F. Dean Toste

  DOI：10.1021/ja1095045

  日期：2011.3.16

  reactions with electron-deficient alkenes and N-sulfonyl aldimines to give products of 1,3-dipolar cycloaddition and Mannich addition reactions, respectively. Both of these reactions proceed with good to excellent diastereo- and enantioselectivity using a single class of gold catalysts, namely C(2)-symmetric bis(phosphinegold(I) carboxylate) complexes. The development of the azlactone Mannich reaction to

  吖内酯参与与缺电子烯烃和N-磺酰醛亚胺的立体选择性反应，分别产生1,3-偶极环加成和曼尼希加成反应的产物。这两个反应均使用一类金催化剂，即 C(2)-对称双(膦金(I)羧酸酯)络合物，以良好至优异的非对映选择性和对映选择性进行。描述了二氢唑酮曼尼希反应的发展，以提供完全保护的抗 α,β-二氨基酸衍生物。研究了几种无环 1,2-二取代烯烃的 1,3-偶极环加成反应以及所得环加合物的化学性质，以探讨该反应的立体化学过程。报告了环加成反应和曼尼希反应的反应动力学和串联质谱研究。这些研究支持了一种机制，其中金络合物通过亲核试剂活化而不是更典型的亲电子反应组分的活化来催化加成反应。
• 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。
• Multi-substituted imidazolines and method of use thereof
  申请人：Board of Trustees of MICHIGAN STATE UNIVERSITY

  公开号：US20030232870A1

  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 B. subtillus and B. cereus with MIC values in the range of 50 &mgr;m/mL.

  描述了一类新型的咪唑啉，作为4位酸或酯，具有非常强大的抗炎和抗微生物活性。这些咪唑啉的合成包括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，可用于治疗脓毒性休克以及许多其他炎症（关节炎和哮喘）和传染性疾病。描述了这种新型非甾体类抗炎药物（用于哮喘等的治疗）、抗菌药物和防腐剂的用途。这些化合物还可用于肿瘤的治疗（如癌症）。咪唑啉是转录因子NF-κB的强效抑制剂，并对革兰氏阳性细菌B. subtillus和B. cereus具有强大的活性，MIC值在50 μm/mL的范围内。
• Highly Diastereoselective Multicomponent Synthesis of Unsymmetrical Imidazolines
  作者：Satymaheshwar Peddibhotla、S. Jayakumar、Jetze J. Tepe

  DOI：10.1021/ol026703y

  日期：2002.10.1

  We report here a highly diastereoselective multicomponent synthesis of imidazolines. These low molecular weight scaffolds contain a four-point diversity applicable to alkyl, aryl, acyl, and hetereocyclic substitutions. [structure: see text]

  我们在这里报告了咪唑啉的高度非对映选择性的多组分合成。这些低分子量支架包含适用于烷基，芳基，酰基和杂环取代的四点多样性。[结构：见文字]