(1S,2R,6S,8R)-5-(3-cyclohexylpropanoyl)-11,11-dimethyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one | 176965-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,6S,8R)-5-(3-cyclohexylpropanoyl)-11,11-dimethyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
• CAS: 176965-53-0
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: WHTVQFQXIYBLCC-BVUBDWEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (1S,2R,6S,8R)-5-(3-cyclohexylpropanoyl)-11,11-dimethyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 (3aS,4aR,8aS,8bR)-3-((R)-3-Cyclohexyl-2-methyl-propionyl)-7,7-dimethyl-hexahydro-[1,3]dioxino[4',5':4,5]furo[2,3-d]oxazol-2-one 、 (3aS,4aR,8aS,8bR)-3-((S)-3-Cyclohexyl-2-methyl-propionyl)-7,7-dimethyl-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 alkylations

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00052-3
• 作为产物：
  描述：

  3,5-O-isopropylidene-α-D-xylofurano-<1,2-d>oxazolidin-2'-one 、 3-环己基丙酰氯 在 正丁基锂 作用下， 生成 (1S,2R,6S,8R)-5-(3-cyclohexylpropanoyl)-11,11-dimethyl-3,7,10,12-tetraoxa-5-azatricyclo[6.4.0.02,6]dodecan-4-one
  参考文献：
  名称：

  D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00052-3

文献信息

• D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations
  作者：Peter Köll、Arne Lützen

  DOI：10.1016/0957-4166(96)00052-3

  日期：1996.3

  Chiral N-acylated oxazolidin-2-ones readily available from D-xylose have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide enolates to afford alpha-branched products. These are easily purified and hydrolyzed without difficulty allowing isolation of the desired ramified carboxylic acids in high enantiomeric excesses and to return the auxiliaries for reuse. (C) 1996 Elsevier Science Ltd