(E)-(S)-2,2-Dimethyl-non-4-en-3-ol | 167817-96-1

• 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)-2,2-Dimethyl-non-4-en-3-ol
• 英文别名: (E,3S)-2,2-dimethylnon-4-en-3-ol
• CAS: 167817-96-1
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: DXSRWTLSYROVJV-DDXVTDLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-(S)-2,2-Dimethyl-non-4-en-3-ol 在 二甲基硫 、 sodium hydride 、 臭氧 作用下， 生成 (R)-2-Benzyloxy-3,3-dimethyl-butyraldehyde
  参考文献：
  名称：

  Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes

  摘要：

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.

  DOI：

  10.1021/jo00112a012
• 作为产物：
  描述：

  (E)-2-庚烯醛 、 magnesium,2-methylpropane,bromide 生成 (E)-(S)-2,2-Dimethyl-non-4-en-3-ol
  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：——