(3aS,4aR,7S,8aS,8bR)-3-Acetyl-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one | 191287-15-7

• 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: (3aS,4aR,7S,8aS,8bR)-3-Acetyl-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
• 英文别名: (1S,2R,6S,8R,11S)-5-acetyl-11-phenyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 191287-15-7
• 化学式: C₁₅H₁₅NO₆
• 分子量: 305.287
• InChiKey: GKYNWCKVRWXPDD-BJJPWKGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (3aS,4aR,7S,8aS,8bR)-3-Acetyl-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 在 lithium hexamethyldisilazane 作用下， 生成 (3aS,4aR,7S,8aS,8bR)-3-((S)-3-Hydroxy-3-phenyl-propionyl)-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 、 (3aS,4aR,7S,8aS,8bR)-3-((R)-3-hydroxy-3-phenylpropanoyl)-7-phenylhexahydro-2H-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
  参考文献：
  名称：

  d-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions

  摘要：

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00096-7
• 作为产物：
  描述：

  α-D-xylofurano<1,2,d>oxazolidin-2'-one 在 正丁基锂 、 zinc(II) chloride 作用下， 反应 5.17h， 生成 (3aS,4aR,7S,8aS,8bR)-3-Acetyl-7-phenyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one
  参考文献：
  名称：

  d-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions

  摘要：

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00096-7

文献信息

• d-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions
  作者：Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(97)00096-7

  日期：1997.4

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.