(E)-(S)-4-Hydroxy-5,5-dimethyl-hex-2-enoic acid ethyl ester | 148929-70-8

• 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: (E)-(S)-4-Hydroxy-5,5-dimethyl-hex-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4S)-4-hydroxy-5,5-dimethylhex-2-enoate
• CAS: 148929-70-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: KRYZCTPWHGVGSU-CZEYKFRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (E)-(S)-4-Hydroxy-5,5-dimethyl-hex-2-enoic acid ethyl ester 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-hex-2-enoic acid ethyl ester
  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)-2,2-Dimethyl-non-4-en-3-ol 在 二甲基硫 、 臭氧 作用下， 生成 (E)-(S)-4-Hydroxy-5,5-dimethyl-hex-2-enoic acid ethyl ester
  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

文献信息

• Gung Benjamin W., Wolf Mark A., Zhu Zhaohai, J. Org. Chem., 58 (1993) N 2, S 3350-3354
  作者：Gung Benjamin W., Wolf Mark A., Zhu Zhaohai

  DOI：——

  日期：——