(S)-3-acryloyl-4-(tert-butyl)oxazolidin-2-one | 506444-76-4

• 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: (S)-3-acryloyl-4-(tert-butyl)oxazolidin-2-one
• 英文别名: (4S)-3-Acryloyl-4-tert-butyl-1,3-oxazolidin-2-one；(4S)-4-tert-butyl-3-prop-2-enoyl-1,3-oxazolidin-2-one
• CAS: 506444-76-4
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: DRSHJSYDDUCSKF-SSDOTTSWSA-N

物化性质

• 沸点：
  247.1±23.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (S)-3-acryloyl-4-(tert-butyl)oxazolidin-2-one 在 C₃₅H₅₂AuNOP⁽¹⁺⁾*F₆Sb^(1-) 、 gadolinium(III) trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  通过 AuI 催化的单锅级联对萜类支架进行发散和模块化合成

  摘要：

  涉及外-Diels-Alder 反应和路易斯酸金（I）催化环化的一锅序列允许访问三个复杂的多环支架。通过改变溶剂和金 (I) 催化剂的配体，可以获得结构多样性。额外的 Diels-Alder 步骤生成了拥有多达 5 个立体中心的四环核。

  DOI：

  10.1002/anie.202110575
• 作为产物：
  描述：

  L-叔亮氨醇 在 氢氧化钾 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.25h， 生成 (S)-3-acryloyl-4-(tert-butyl)oxazolidin-2-one
  参考文献：
  名称：

  Experimental Determination of the Absolute Enantioselectivity of an Antibody-Catalyzed Diels−Alder Reaction and Theoretical Explorations of the Origins of Stereoselectivity

  摘要：

  The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene- 1 carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition-state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.

  DOI：

  10.1021/ja020879d

文献信息

• Synthesis and structural characterization of a monocarboxylic inhibitor for GRB2 SH2 domain
  作者：Tao Xiao、Luxin Sun、Min Zhang、Zilu Li、Eric B. Haura、Ernst Schonbrunn、Haitao Ji

  DOI：10.1016/j.bmcl.2021.128354

  日期：2021.11

  A monocarboxylic inhibitor was designed and synthesized to disrupt the protein–protein interaction (PPI) between GRB2 and phosphotyrosine-containing proteins. Biochemical characterizations show compound 7 binds with the Src homology 2 (SH2) domain of GRB2 and is more potent than EGFR1068 phosphopeptide 14-mer. X-ray crystallographic studies demonstrate compound 7 occupies the GRB2 binding site for

  设计并合成了一种单羧酸抑制剂来破坏 GRB2 和含磷酸酪氨酸的蛋白质之间的蛋白质相互作用 (PPI)。生化表征显示化合物7与 GRB2 的 Src 同源 2 (SH2) 结构域结合，并且比 EGFR 1068磷酸肽 14-mer 更有效。X 射线晶体学研究表明，化合物7占据了含有磷酸酪氨酸序列的 GRB2 结合位点，并揭示了 GRB2 抑制剂结合的关键结构特征。这种具有 –1 正式电荷的化合物为结构优化提供了新的方向，从而为异常 Ras-MAPK 信号级联的这一关键蛋白靶点生成细胞渗透性抑制剂。
• SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
  作者：Steven D. Bull、Stephen G. Davies、A. Christopher Garner、Dennis Kruchinin、Min-Suk Key、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b605244d

  日期：——

  The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels–Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。
• Electronically unfavorable addition of electron-deficient olefins to isochromenylium tetrafluoroborates initiated by C-1 O-glycosylation
  作者：Shu-Yan Yu、Zhi-Long Hu、Hao Zhang、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2012.03.106

  日期：2012.5

  and electron-deficient olefins have been studied and achieved by assistance of a phenolic hydroxyl group in the olefin substrates, providing the corresponding 2-oxabicyclo[3.3.1]nonane derivatives diastereoselectively in moderate to satisfactory yields. The new methodology is initiated by an intermolecular C-1 O-glycosylation, and completed with an intramolecular Michael addition and an aldol condensation

  已经研究并通过在烯烃底物中的酚羟基的帮助下实现了异氟氰化四氟硼酸酯与缺电子烯烃之间的电子不利反应，并以中等至令人满意的收率选择性地非对映地提供了相应的2-氧杂双环[3.3.1]壬烷衍生物。新的方法是由分子间的C-1 O-糖基化引发的，并以分子内迈克尔加成反应和级联方式的羟醛缩合反应完成。
• A Silica‐Supported Yttrium Triflate Packed Bed Reactor for Continuous Flow Michael Addition of Indoles to Benzylidene Malonates
  作者：Emanuela Donato、Valerio Chiroli、Alessandra Puglisi、Maurizio Benaglia

  DOI：10.1002/adsc.202301210

  日期：2024.2.20

  The catalytic properties of packed bed reactors filled with Y(OTf)3 immobilised onto functionalised silica have been tested in the Michael addition of indoles to benzylidene malonates under flow conditions, providing improved productivity over the batch conditions, a greater ease of recovery of the final products and a prolonged life of the catalyst. Noteworthy, the same catalytic reactor, after being

  填充床反应器填充有固定在功能化二氧化硅上的 Y(OTf)3 的催化性能已经在流动条件下吲哚与亚苄基丙二酸酯的迈克尔加成中进行了测试，与间歇条件相比提供了更高的生产率，更容易回收最终产物。产品和催化剂的使用寿命延长。值得注意的是，同一个催化反应器在使用五天后，被用来进行不同的反应，即流动中的立体选择性狄尔斯阿尔德环加成反应，与间歇反应相比，生产率提高了 24 倍。
• Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with <i>N</i>-Chloro-<i>N</i>-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts
  作者：Yuta Murakami、Youhei Takeda、Satoshi Minakata

  DOI：10.1021/jo2010632

  日期：2011.8.5

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.