4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one | 97485-17-1

• 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: 4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one
• 英文别名: 4-((1H-indol-3-yl)methyl)-2-phenyloxazol-5(4H)-one；4-(1H-indol-3-yl-methyl)-2-phenyl-4H-oxazol-5-one；4-((1H-3-indolyl)methyl)-2-phenyloxazol-5(4H)-one；2-phenyl-4-[(1H-indol-3-yl)methyl]-5(4H)-oxazolone；4-[(1H-Indol-3-yl)methyl]-2-phenyl-1,3-oxazol-5(4H)-one；4-(1H-indol-3-ylmethyl)-2-phenyl-4H-1,3-oxazol-5-one
• CAS: 97485-17-1
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: XHIVMGAINOFTFU-UHFFFAOYSA-N

物化性质

• 沸点：
  488.1±37.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one 在 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 1-((1H-indol-3-yl)methyl)-1,3a,4,5,6,6a-hexahydro-4,6-dioxo-3,5-diphenylpyrrolo[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-benzoyl-D,L-tryptophan 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， 以80%的产率得到4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one
  参考文献：
  名称：

  硅介导的 1,3-偶极环加成多组分合成高取代咪唑啉

  摘要：

  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。

  DOI：

  10.1055/s-2003-40196

文献信息

• Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters
  作者：Kunru Yu、Xiaohua Liu、Xiaobin Lin、Lili Lin、Xiaoming Feng

  DOI：10.1039/c5cc05534b

  日期：——

  We have developed a chiral bisguanidinium salt catalyzed dynamic kinetic resolution of azlactones with oximes. A variety of chiral N-acyl amino acid oxime esters were generated with up to 97% ee and 99% yield. The products are useful in peptide synthesis.

  我们已经开发了一种手性双胍盐催化肟与a内酯的动力学动力学拆分。产生了多种手性N-酰基氨基酸肟酯，其收率高达97％ee，收率高达99％。该产品可用于肽合成。
• One-Pot Preparation of Oxazol-5(4<i>H</i>)-ones from Amino Acids in Aqueous Solvents
  作者：Hikaru Fujita、Munetaka Kunishima

  DOI：10.1248/cpb.c12-00291

  日期：——

  method for one-pot synthesis of oxazol-5(4H)-ones has been developed using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), which is available for the activation of carboxylic acids in an aqueous solvent. The oxazolones were prepared by the N-acylation of amino acids with carboxylic acids and the subsequent cyclodehydration of the resulting N-acylamino acids by the addition

  使用4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉氯化物（DMT-MM）开发了一种一锅合成oxazol-5（4H）-的方法），可用于在水性溶剂中活化羧酸。通过将氨基酸与羧酸进行N-酰化反应，然后通过添加N，N-二乙基苯胺对所得的N-酰基氨基酸进行环脱水反应，制得恶唑酮。由于这两种反应都是在水性溶剂中使用相同的偶联剂DMT-MM有效地进行的，因此简化了程序并易于进行。另外，通过控制反应体系的碱性已经合成了5-（三嗪基氧基）恶唑衍生物。
• Chemo-enzymatic asymmetric synthesis of amino acids. Enantioselective hydrolyses of 2-phenyl-oxazolin-5-ones.
  作者：Rui-Lin Gu、Ik-Soo Lee、Charles J. Sih

  DOI：10.1016/0040-4039(92)88111-h

  日期：1992.4

  Porcine pancreatic lipase and the lipase of Aspergillus niger catalyze the enantioselective hydrolysis of a series of 4-substituted-2-phenyl-oxazolin-5-ones to yield optically active ()-and ()-N-benzoyl amino acids respectively.

  猪胰脂肪酶和黑曲霉的脂肪酶催化一系列4-取代的-2-苯基-恶唑啉-5-酮的对映选择性水解，分别产生光学活性的（）-和（）-N-苯甲酰基氨基酸。
• Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones
  作者：Shunxi Dong、Xiaohua Liu、Yin Zhu、Peng He、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja404379n

  日期：2013.7.10

  example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and

  使用手性双胍盐实现吖内酯与恶氮丙啶氧胺化的第一个实例。氧氮丙啶的高效催化不对称氧化胺化和动力学拆分同时发生。获得了具有潜在生物活性的各种手性 oxazolin-4-one 衍生物（高达 92% ee）。同时，回收了一系列光学纯氧氮杂环丙烷，ee 高达 99%，并成功用于 3-甲基-1H-吲哚和苯乙烯的不对称氧化胺化。还通过对照实验研究了三重立体分化过程。
• 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。