prop-2-enyl (5S)-3-[(1S)-1-[(3S)-3-hydroxybutanoyl]oxyethyl]-4,5-dihydro-1,2-oxazole-5-carboxylate | 1161025-70-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: prop-2-enyl (5S)-3-[(1S)-1-[(3S)-3-hydroxybutanoyl]oxyethyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 1161025-70-2
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: DLNLMJVLBFKJNZ-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (5S)-3-[(1S)-1-[(3S)-3-hydroxybutanoyl]oxyethyl]-4,5-dihydro-1,2-oxazole-5-carboxylate 在 吗啉 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 2,6-二叔丁基吡啶 、 乙基溴化镁 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Synthesis-Based Structural Elucidation of (‒)-Macrosphelides J and K

  摘要：

  The structures of (-)-macrosphelides J and K have been elucidated via asymmetric total syntheses. Key points of the structure elucidation include an initial prediction of the stereochemistries of (-)-macrosphelides J and K based on the structural relationship of the macrosphelides and molecular modeling of macrosphelide B. Our synthetic approach features an isoxazoline-based route involving a diastereoselective olefin-nitrile oxide cycloaddition, an intricate reductive N-O bond cleavage of an isoxazoline and O-alkylation of the labile beta-hydroxy ketone intermediate.

  DOI：

  10.3987/com-15-13195
• 作为产物：
  描述：

  C₂₄H₃₂N₂O₆S 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 prop-2-enyl (5S)-3-[(1S)-1-[(3S)-3-hydroxybutanoyl]oxyethyl]-4,5-dihydro-1,2-oxazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and Synthesis-Based Structural Elucidation of (‒)-Macrosphelides J and K

  摘要：

  The structures of (-)-macrosphelides J and K have been elucidated via asymmetric total syntheses. Key points of the structure elucidation include an initial prediction of the stereochemistries of (-)-macrosphelides J and K based on the structural relationship of the macrosphelides and molecular modeling of macrosphelide B. Our synthetic approach features an isoxazoline-based route involving a diastereoselective olefin-nitrile oxide cycloaddition, an intricate reductive N-O bond cleavage of an isoxazoline and O-alkylation of the labile beta-hydroxy ketone intermediate.

  DOI：

  10.3987/com-15-13195

文献信息

• First total syntheses of (−)-macrosphelides J and K and elucidation of their absolute configuration
  作者：Hwayoung Yun、Seung-Mann Paek、Jong-Wha Jung、Nam-Jung Kim、Seok-Ho Kim、Young-Ger Suh

  DOI：10.1039/b817693k

  日期：——

  First total syntheses of (–)-macrosphelides J and K and their structural elucidation are described.

  首次介绍了 (â)-macrosphelides J 和 K 的全合成及其结构解析。
• Synthesis and Synthesis-Based Structural Elucidation of (‒)-Macrosphelides J and K
  作者：Hwayoung Yun、Hongchan An、Seung-Hee Kim、Heegyu Kim、Kyeojin Kim、Jaehoon Sim、Jaebong Jang、Seung-Mann Paek

  DOI：10.3987/com-15-13195

  日期：——

  The structures of (-)-macrosphelides J and K have been elucidated via asymmetric total syntheses. Key points of the structure elucidation include an initial prediction of the stereochemistries of (-)-macrosphelides J and K based on the structural relationship of the macrosphelides and molecular modeling of macrosphelide B. Our synthetic approach features an isoxazoline-based route involving a diastereoselective olefin-nitrile oxide cycloaddition, an intricate reductive N-O bond cleavage of an isoxazoline and O-alkylation of the labile beta-hydroxy ketone intermediate.