(4S)-4-isobutyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one | 155727-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S)-4-isobutyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• 英文别名: (S)-3-cinnamoyl-4-isobutyloxazolidin-2-one；(4S)-4-(2-methylpropyl)-3-[(E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 155727-84-7
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: IVMFXSPETHQCNV-VFNNOXKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (4S)-4-isobutyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 在 tetrabutylammonium borohydride 、 四乙基对甲苯磺酸铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4R,5R)-4,5-diphenyltetrahydrofuran-2-one
  参考文献：
  名称：

  Stereoselective coupling of optically active 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides by electroreduction

  摘要：

  The electronduction of chiral 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides gave beta-acylated products stereoselectively. The products were transformed to optically active cis-beta,gamma-disubstituted-gamma-lactones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01720-7
• 作为产物：
  描述：

  L-亮氨醇 在 铁酞菁 、 3,3',5,5'-四叔丁基-4,4'-联苯醌 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 生成 (4S)-4-isobutyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  通过好氧氧化NHC催化N-酰化恶唑烷酮

  摘要：

  报道了使用好氧氧化NHC催化合成有用的恶唑烷酮与醛的第一个N-酰化反应。该反应以良好至优异的产率提供了广泛范围的官能化的恶唑烷酮。仔细选择电子传递介体被证明对实现有效的好氧N酰化至关重要，以前证明使用NHC催化是困难的。该方法允许温和地进入酰化的恶唑烷酮，避免使用危险的和反应性的预官能化底物。

  DOI：

  10.1021/acs.joc.8b01723

文献信息

• Diastereoselective Ru-Catalyzed Cross-Metathesis−Dihydroxylation Sequence. An Efficient Approach toward Enantiomerically Enriched <i>syn</i>-Diols
  作者：N. Matthias Neisius、Bernd Plietker

  DOI：10.1021/jo800145x

  日期：2008.4.1

  metathesis reactions allows for a stereoselective subsequent RuO4-catalyzed dihydroxylation. The sequence is concluded by an unusual kinetic resolution of the diastereomeric diols obtained in the oxidation reaction. As a consequence a variety of structurally diverse enantiomerically enriched diols are obtained. To the best of our knowledge the results summarized in this paper represent the first highly efficient

  在过去的几年中，顺序催化已经发展成为一个有力的概念，可以在有机合成中更有效地使用催化活性的昂贵过渡金属。在本文中，我们介绍了各种烯烃与手性辅助取代的丙烯酰胺的立体选择性交叉复分解-二羟基化反应。在复分解反应中引入的手性信息（即辅助信息）可用于后续的立体选择性RuO 4。-催化的二羟基化。该序列由氧化反应中获得的非对映体二醇的异常动力学拆分而得出。结果，获得了多种结构上不同的对映体富集的二醇。据我们所知，本文总结的结果代表了第一个高效的非对映选择性RuO 4催化氧化。
• Enantioselective synthesis of dimethyl 3,4-diphenyladipate by electroreductive hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones
  作者：Naoki Kise、Mitsuaki Echigo、Tatsuya Shono

  DOI：10.1016/s0040-4039(00)73190-x

  日期：1994.3

  Dimethyl(3R,4R)- and (3S,4S)-diphenyladipate were synthesized enantioselectively by electroreductive intermolecular hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones and subsequent methanolysis.
• Stereoselective Hydrocoupling of Optically Active 3-<i>trans</i>-Cinnamoyloxazolidinones by Electroreduction
  作者：Naoki Kise、Syun-ichiro Mashiba、Nasuo Ueda

  DOI：10.1021/jo981231f

  日期：1998.10.1

  Reductive hydrocoupling of chiral 3-trans-cinnamoyloxazolidinones was studied by an electro chemical method. The electroreduction was performed conveniently at a constant current using an undivided cell. The stereoselectivity of the hydrodimers was strongly affected by the electrolyte employed. Electroreduction of (S)-4-isobutyl-3-trans-cinnamoyloxazolidinone 1a in 0.3 M Et4NOTs/AN gave a mixture of two diastereomers of all-trans cyclized hydrodimer 2a, and the selectivity was R,S,R/S,R,S = 85:15. On the other hand, the reduction of 1a in 1.7 M LiClO4/THF afforded a diastereomeric mixture of hydrodimers in a selectivity of R,R/S,S/R,S = 5:52:43. The stereoselectivities were explained by considering stable conformations of intermediate anion radicals, that is, syn-Z type for naked anion radicals and anti-Z type for lithiated anion radicals. Semiempirical calculations also supported this hypothesis. Electroreductions of (S)-4-isobutyl-3-cis-cinnamoyloxazolidinone and (S)-4-isobutyl-3-phenylpropioloyloxazolidinone gave 2a in the same stereoselectivity as electroreduction of 1a did. The electroreductive hydrocoupling was not inhibited by para and meta substitution on the aryl group of 3-trans-cinnamoyloxazolidinones. An ortho substitution, however, hindered the hydrocoupling and lowered the stereoselectivity of the hydrodimers. Electroreduction of 3-trans-cinnamoyloxazolidinethione and thiazolidinethione gave trans-3,4-diphenylcyclopentanone as a product, and the stereoselectivities were similar to that obtained from the corresponding oxazolidinone.
• <i>N</i>-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis
  作者：Linda Ta、Anton Axelsson、Henrik Sundén

  DOI：10.1021/acs.joc.8b01723

  日期：2018.10.5

  synthetically useful oxazolidinones with aldehydes using aerobic oxidative NHC catalysis is reported. The reaction offers a broad scope of functionalized oxazolidinones in good to excellent yields. Careful choice of electron transfer mediators proved pivotal to achieve efficient aerobic N-acylation, which has previously proven difficult using NHC catalysis. The methodology allows a mild entry to acylated oxazolidinones

  报道了使用好氧氧化NHC催化合成有用的恶唑烷酮与醛的第一个N-酰化反应。该反应以良好至优异的产率提供了广泛范围的官能化的恶唑烷酮。仔细选择电子传递介体被证明对实现有效的好氧N酰化至关重要，以前证明使用NHC催化是困难的。该方法允许温和地进入酰化的恶唑烷酮，避免使用危险的和反应性的预官能化底物。
• Stereoselective coupling of optically active 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides by electroreduction
  作者：Naoki Kise、Yoshihiko Hirata、Takaaki Hamaguchi、Nasuo Ueda

  DOI：10.1016/s0040-4039(99)01720-7

  日期：1999.11

  The electronduction of chiral 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides gave beta-acylated products stereoselectively. The products were transformed to optically active cis-beta,gamma-disubstituted-gamma-lactones. (C) 1999 Elsevier Science Ltd. All rights reserved.