tert-butyl (2E)-4-[(3aS,7aS)-hexahydro-2-oxo-1,3-benzoxazol-3(2H)-yl]-4-oxobut-2-enoate | 1408186-39-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (2E)-4-[(3aS,7aS)-hexahydro-2-oxo-1,3-benzoxazol-3(2H)-yl]-4-oxobut-2-enoate
• 英文别名: tert-butyl (E)-4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazol-3-yl]-4-oxobut-2-enoate
• CAS: 1408186-39-9
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: KWLPPFZKHOLVCK-WRSFFWLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2E)-4-[(3aS,7aS)-hexahydro-2-oxo-1,3-benzoxazol-3(2H)-yl]-4-oxobut-2-enoate 在 lithium hydroxide monohydrate 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (3S)-3-[(tert-butoxy)carbonyl]-4,4-dimethylpentanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis ofβ²-homo-tert-LeucineviaRadical Addition to EnantiopureN-Fumaroylhexahydrobenzooxazolidin-2-one

  摘要：

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.

  DOI：

  10.1002/hlca.201200448
• 作为产物：
  描述：

  富马酸叔-丁酯 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.5h， 生成 tert-butyl (2E)-4-[(3aS,7aS)-hexahydro-2-oxo-1,3-benzoxazol-3(2H)-yl]-4-oxobut-2-enoate
  参考文献：
  名称：

  Asymmetric Synthesis ofβ²-homo-tert-LeucineviaRadical Addition to EnantiopureN-Fumaroylhexahydrobenzooxazolidin-2-one

  摘要：

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.

  DOI：

  10.1002/hlca.201200448

文献信息

• Asymmetric Synthesis of<i>β</i>²-homo-<i>tert</i>-Leucine<i>via</i>Radical Addition to Enantiopure<i>N</i>-Fumaroylhexahydrobenzooxazolidin-2-one
  作者：Margarita Escudero-Casao、Eusebio Juaristi

  DOI：10.1002/hlca.201200448

  日期：2012.10

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.