3-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-2-oxazolidinone | 137542-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-2-oxazolidinone
• 英文别名: (E)-3-(2-methyl-1-oxo-2-buten-1-yl)-2-oxazolidinone；3-(1-oxo-2-methyl-2-butenyl)-2-oxazolidinone；(E)-3-(2-methylbut-2-enoyl)oxazolidin-2-one；N-tigloylisoxazolidinone；3-[(E)-2-methylbut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 137542-42-8
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: AADSCRHWHRHAGN-ZZXKWVIFSA-N

物化性质

• 沸点：
  233.7±23.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-2-oxazolidinone 在 palladium 10% on activated carbon 、 C₂₇H₂₈N₂O₂ magnesium(II) perchlorate 、 氢气 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， -40.0~60.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (2R,3R)-3-amino-2-methyl-butyric acid
  参考文献：
  名称：

  BETA-AMINO ACIDS AND METHODS AND INTERMEDIATES FOR MAKING SAME

  摘要：

  披露了未在β位取代的β-氨基酸；在β位用芳基取代的β-氨基酸；在α位用芳基取代的β-氨基酸；在α位带有两个取代基的β-氨基酸；和/或在α和β位用与α和β位的碳原子一起形成环的基团取代的β-氨基酸。还披露了制备上述β-氨基酸和其他β-氨基酸的方法，包括提供α，β-不饱和亚胺；将α，β-不饱和亚胺转化为2-取代异噁唑啉-5-酮；将2-取代异噁唑啉-5-酮转化为β-氨基酸。

  公开号：

  US20110218342A1
• 作为产物：
  描述：

  惕格酸 在 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective Synthesis of α,β-Disubstituted-β-amino Acids

  摘要：

  Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.

  DOI：

  10.1021/ja0372309

文献信息

• Enantioselective Enolate Protonation in Sulfa–Michael Addition to α-Substituted <i>N</i>-Acryloyloxazolidin-2-ones with Bifunctional Organocatalyst
  作者：Nirmal K. Rana、Vinod K. Singh

  DOI：10.1021/ol202808n

  日期：2011.12.16

  Organocatalytic conjugate addition of thiols to α-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically

  在金鸡纳生物碱衍生的硫脲的存在下，已经研究了硫醇向α-取代的N-丙烯酰基恶唑烷丁二酮的有机催化共轭加成反应，然后进行不对称质子化。使用假对映异构体奎宁/奎尼丁衍生的催化剂，两种对映体都可以以相同水平的对映体选择性获得。加成/质子化产物已转化为有用的生物活性分子。
• Conjugate addition of allylsilanes to α,β-unsaturated N-acyloxazolidinones
  作者：Ming-Jung Wu、Jiann-Yih Yeh

  DOI：10.1016/s0040-4020(01)80818-8

  日期：1994.1

  The conjugate addition of allyltrimethylsilane to alpha,beta-unsaturated N-acyloxazolidinone at -78 degrees C in the presence of TiCl4 gave the allylation product 3. However, when the reaction was carded out at room temperature, a small amount of cyclopentane adduct 4 was observed. The cyclopentane product formation can be prevented by employing BF3.OEt(2) as a Lewis acid. The enantioselective synthesis of optically pure 3-substituted-5-hexenoic acids was achieved by employing chiral oxazolidinone as a chiral auxiliary.
• Stereospecific nucleophilic addition reactions to olefins. Addition of thiols to .alpha.,.beta.-unsaturated carboxylic acid derivatives
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito、Tadamasa Date、Kimio Okamura、Satoshi Inagaki

  DOI：10.1021/jo00023a021

  日期：1991.11

  Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.
• Synthesis of (±)-Nosyberkol (Isotuberculosinol, Revised Structure of Edaxadiene) and (±)-Tuberculosinol
  作者：Nathan Maugel、Francis M. Mann、Matthew L. Hillwig、Reuben J. Peters、Barry B. Snider

  DOI：10.1021/ol100832h

  日期：2010.6.4

  Me(2)AlCl-catalyzed Diels-Alder reaction of N-tigloyloxazolidinone with 6,6-dimethyl-1-vinylcyclohexene selectively provided the exo adduct, which was converted to nosyberkol (isotuberculosinol) and tuberculosinol. The spectral data for nosyberkol are identical with those reported for edaxadiene, whose structure is revised accordingly.
• MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
  申请人：Gilead Sciences, Inc.

  公开号：EP2861604B1

  公开（公告）日：2017-03-01