(4S)-4-benzyl-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one | 583826-87-3

• 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-benzyl-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 583826-87-3
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: NBHLYULFHPLPRN-KAMXEHQASA-N

物化性质

• 沸点：
  513.3±60.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one 在 盐酸 、 sodium periodate 、 lithium bromide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 、 (4S)-4-benzyl-3-[(2S,3S)-2-bromo-3-(3,4-dimethoxyphenyl)-3-hydroxypropanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa

  摘要：

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.109
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酰氯 、 (S)-4-苄基-2-唑烷酮 生成 (4S)-4-benzyl-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  获得对映体纯 2,5-二芳基四氢呋喃 - 在 (-)-Virgatusin 和 (+)-Urinaligran 合成中的应用

  摘要：

  非对映选择性 MnIII 促进的 β-氧代酯 1 与 N-肉桂酰恶唑烷酮 2 的自由基加成得到 2,3-二氢呋喃 3。在 C=C 键催化氢化后，然后还原去除手性助剂，得到对映纯的四氢呋喃 5分两步转化为天然存在的 (-)-virgatusin 和 (+)-urinaligran 以及另外两种非天然的四取代 THF 木脂素。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900099

文献信息

• Asymmetric Radical Synthesis of 2,5-Diaryl-2,3-dihydrofurans − Application to the Preparation of (+)-Phyltetralin
  作者：Frédéric Garzino、Alain Méou、Pierre Brun

  DOI：10.1002/ejoc.200390198

  日期：2003.4

  The diastereoselective MnIII-promoted radical addition of β-oxo ester 1 onto N-cinnamoyloxazolidinone 2 affords, after removal of the chiral auxiliary, the enantiopure 2,5-diaryl-2,3-dihydrofuran (−)-4. Its SnCl4-induced rearrangement leads to a 4-aryltetralone immediate precursor of the aryltetralin lignan (+)-phyltetralin (9). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  β-氧代酯 1 与 N-肉桂酰恶唑烷酮 2 的非对映选择性 MnIII 促进的自由基加成在去除手性助剂后得到对映体纯的 2,5-二芳基-2,3-二氢呋喃 (-)-4。其 SnCl4 诱导的重排导致 4-芳基四氢萘酮直接前体的芳基四氢萘木酚素 (+)-phyltetralin (9)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa
  作者：Shyla George、Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.12.109

  日期：2007.2

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.
• Access to Enantiopure 2,5-Diaryltetrahydrofurans - Application to the Synthesis of (-)-Virgatusin and (+)-Urinaligran
  作者：Sophie Martinet、Alain Méou、Pierre Brun

  DOI：10.1002/ejoc.200900099

  日期：2009.5

  afforded 2,3-dihydrofurans 3. After catalytic hydrogenation of the C=C bond, followed by reductive removal of the chiral auxiliary, the resulting enantiopure tetrahydrofurans 5 were transformed in two steps into naturally occurring (–)-virgatusin and (+)-urinaligran and two other, nonnatural, tetrasubstituted THF lignans. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  非对映选择性 MnIII 促进的 β-氧代酯 1 与 N-肉桂酰恶唑烷酮 2 的自由基加成得到 2,3-二氢呋喃 3。在 C=C 键催化氢化后，然后还原去除手性助剂，得到对映纯的四氢呋喃 5分两步转化为天然存在的 (-)-virgatusin 和 (+)-urinaligran 以及另外两种非天然的四取代 THF 木脂素。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)