(R)-2-Methoxy-3,3-dimethyl-butyraldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-Methoxy-3,3-dimethyl-butyraldehyde
• 英文别名: (2R)-2-methoxy-3,3-dimethylbutanal
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: HBVIGQGBIVBGJI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Methoxy-3,3-dimethyl-butyraldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 生成 Ethyl 4-methoxy-5,5-dimethyl-2(E)-hexenoate
  参考文献：
  名称：

  Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers

  摘要：

  A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the gamma-hydroxy-alpha,beta-unsaturated esters, which normally favor the CO-eclipsed form (II). On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the gamma-hydroxy-alpha,beta-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes. These facts are explained by the size of the allylic oxygen lone pairs.

  DOI：

  10.1021/jo00077a023
• 作为产物：
  描述：

  (E)-(S)-4-Methoxy-5,5-dimethyl-hex-2-ene 在 二甲基硫 、 臭氧 作用下， 生成 (R)-2-Methoxy-3,3-dimethyl-butyraldehyde
  参考文献：
  名称：

  Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers

  摘要：

  A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the gamma-hydroxy-alpha,beta-unsaturated esters, which normally favor the CO-eclipsed form (II). On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the gamma-hydroxy-alpha,beta-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes. These facts are explained by the size of the allylic oxygen lone pairs.

  DOI：

  10.1021/jo00077a023