2-methyl-4-iso-propyl-4H-oxazolin-5-one | 78654-98-5

• 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-iso-propyl-4H-oxazolin-5-one
• 英文别名: 2-methyl-4-isopropyl-2-oxazolin-5-one；4-isopropyl-2-methyloxazol-5(4H)-one；2-methyl-4-isopropyl-5-oxazolone；4-isopropyl-2-methyl-4H-oxazol-5-one；4-Isopropyl-2-methyl-4H-oxazol-5-on；5-Oxo-2-methyl-4-propyl-Δ²-oxazolin；4-Isopropyl-2-methyl-1,3-oxazol-5(4H)-one；2-methyl-4-propan-2-yl-4H-1,3-oxazol-5-one
• CAS: 78654-98-5
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: VSYHWTNTZROWMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-iso-propyl-4H-oxazolin-5-one 在 氢溴酸 作用下， 以 四氢呋喃 、 硝基甲烷 、 水 为溶剂， 反应 7.0h， 生成 N-乙酰-D-缬氨酸
  参考文献：
  名称：

  对映体纯的环状和开放链（R）-和（S）-α，α-二取代α-氨基酸的新通用方法

  摘要：

  制备了各种各样的环状和开链α，α-二取代的α-氨基酸1a-p。通过与衍生自（S）-苯丙氨酸的手性胺15-18偶联，拆分外消旋N-酰化的α，α-二取代氨基酸，形成非对映异构体19/20或21/22，可以通过结晶和/或快速色谱分离在硅胶上（方案3）。通过1,3-恶唑-5（4 H）-酮10a-p的选择性裂解以高收率得到相应的光学纯α，α-二取代氨基酸衍生物11或12（方案3）。α，α-二取代氨基酸的绝对构型由非对映异构体20、21g'，22d的X射线结构确定。

  DOI：

  10.1002/hlca.19920750522
• 作为产物：
  描述：

  氯乙酰基-DL-缬氨酸 在 palladium dichloride sodium benzoate 、 氢气 、 苯甲酸酐 、 三乙胺 作用下， 反应 6.0h， 生成 2-methyl-4-iso-propyl-4H-oxazolin-5-one
  参考文献：
  名称：

  Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted acylaminoacrylic acids. 8. Reductive aminolysis of 4-isopropylidene-oxazol-5-ones

  摘要：

  DOI：

  10.1007/bf00963427

文献信息

• [EN] BENZAMIDE TRPA1 ANTAGONISTS<br/>[FR] BENZAMIDES ANTAGONISTES DE TRPA1
  申请人：ACTURUM LIFE SCIENCE AB

  公开号：WO2014184235A1

  公开（公告）日：2014-11-20

  Compounds of formula I, pharmaceutically acceptable salts thereof, diastereomers, enantiomers, or mixtures thereof: wherein R, X, Y, Z, n and A are as defined in the specification, as well as pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  式I的化合物，其药用盐，非对映体，对映体或其混合物：其中R、X、Y、Z、n和A的定义如规范中所述，以及包括这些化合物的药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理中。
• PREPARATION OF 5-TRIMETHYLSILOXYOXAZOLES FROM 2-OXAZOLIN-5-ONES AND THEIR DIELS–ALDER REACTION: SYNTHESIS OF VITAMIN B₆DERIVATIVES
  作者：Hidetsugu Takagaki、Nobuyoshi Yasuda、Morio Asaoka、Hisashi Takei

  DOI：10.1246/cl.1979.183

  日期：1979.2.5

  of 2-oxazolin-5-ones using chlorotrimethylsilane and triethylamine in high yields. Diels–Alder reaction of the siloxyoxazoles with N-phenylmaleinimide or dimethyl maleate afforded the corresponding substituted pyridines in high yields. This method was applied to the synthesis of Vitamin B6 derivatives starting from N-formylalanine.

  通过使用三甲基氯硅烷和三乙胺对 2-恶唑啉-5-酮进行硅烷化反应，以高产率合成了各种 5-三甲基甲硅烷氧基恶唑。甲硅烷氧基恶唑与 N-苯基马来酰亚胺或马来酸二甲酯的 Diels-Alder 反应以高产率提供了相应的取代吡啶。该方法适用于以 N-甲酰丙氨酸为原料合成维生素 B6 衍生物。
• Diastereochemical Diversity of Imidazoline Scaffolds via Substrate Controlled TMSCl Mediated Cycloaddition of Azlactones
  作者：Vasudha Sharma、Jetze J. Tepe

  DOI：10.1021/ol052118w

  日期：2005.10.1

  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.
• N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor
  作者：Karl S.A. Vallin、Karin J. Sterky、Eva Nyman、Jenny Bernström、Rebecka From、Christian Linde、Alexander B.E. Minidis、Andreas Nolting、Katja Närhi、Ellen M. Santangelo、Fernando W. Sehgelmeble、Daniel Sohn、Jennie Strindlund、Dirk Weigelt

  DOI：10.1016/j.bmcl.2012.07.032

  日期：2012.9

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.
• Study of a new ‘chiral proton’ organocatalyst with hydrolase activity: application in azlactone racemic dynamic resolution
  作者：Ángel L. Fuentes de Arriba、Omayra H. Rubio、Luis Simón、Victoria Alcázar、Laura M. Monleón、Francisca Sanz、Joaquin R. Morán

  DOI：10.1016/j.tetasy.2017.04.012

  日期：2017.6

  For the first time, a 1,3-ketoenol system is described as an acid catalyst with hydrolytic activity. The combination of an enol and a pyridine/benzimidazole supported on a benzofuran skeleton allowed the creation of a novel bifunctional organocatalyst, which has been applied in azlactone racemic dynamic resolution. In spite of the moderate enantioselectivities obtained, the catalyst constitutes a novel concept in the field of chiral Brensted acid catalysis. (C) 2017 Elsevier Ltd. All rights reserved.