4,4-Dibutyl-3-<(2R^*,3S^*)-2,4-dimethyl-3-hydroxyvaleryl>-5,5-pentamethylene-2-oxazolidone | 116616-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 4,4-Dibutyl-3-<(2R^*,3S^*)-2,4-dimethyl-3-hydroxyvaleryl>-5,5-pentamethylene-2-oxazolidone
• 英文别名: 4,4-Dibutyl-3-((2R^*,3S^*)-2,4-dimethyl-3-hydroxyvaleryl)-5,5-pentamethylene-2-oxazolidone；4,4-dibutyl-3-[(2R,3S)-3-hydroxy-2,4-dimethylpentanoyl]-1-oxa-3-azaspiro[4.5]decan-2-one
• CAS: 116616-44-5；116616-45-6
• 化学式: C₂₃H₄₁NO₄
• 分子量: 395.583
• InChiKey: UEDWELRZEQRUGG-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,4-Dibutyl-3-<(2R^*,3S^*)-2,4-dimethyl-3-hydroxyvaleryl>-5,5-pentamethylene-2-oxazolidone 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以72%的产率得到(2R^*,3S^*)-2,4-Dimethyl-3-hydroxyvaleric acid
  参考文献：
  名称：

  Highly stereoselective reformatsky reactions of 3-(2-Bromopropionyl)-2-oxazolidone derivatives with various aldehydes

  摘要：

  The Reformatsky reactions of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities. The highest 2,3-syn-diastereoselectivity (2,3-syn:2,3-anti = 98:2) could be realized at -78-degrees-C by employing sterically crowded 3-(2-bromopropionyl)-4,4-dibutyl-5,5-pentamethylene-2-oxazolidone. While high 2,3-syn-3,4-syn-selectivity (2,3-syn-3,4-syn:2,3-syn-3,4-anti = 94:6) was also accomplished by the reaction with dl-2-phenylpropanal, application of this reaction to enantioselective synthesis of 2,3-syn-aldols was found to be unrewarding. The observed diastereoselectivities could be accounted for by the chelating transition state models.

  DOI：

  10.1016/s0040-4020(01)87087-3
• 作为产物：
  描述：

  3-(2-bromopropionyl)-4,4-dibuthyl-5,5-pentamethylene-2-oxazolidone 、 异丁醛 、 四氢呋喃 生成 4,4-Dibutyl-3-<(2R^*,3S^*)-2,4-dimethyl-3-hydroxyvaleryl>-5,5-pentamethylene-2-oxazolidone
  参考文献：
  名称：

  ITO, YOSHIO;TERASHIMA, SHIRO, TETRAHEDRON LETT., 28,(1987) N 52, 6629-6632

  摘要：

  DOI：

文献信息

• A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes
  作者：Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)96931-4

  日期：——