((E)-(R)-1-Ethyl-hept-2-enyloxymethyl)-benzene | 167563-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((E)-(R)-1-Ethyl-hept-2-enyloxymethyl)-benzene
• 英文别名: [(E,3R)-non-4-en-3-yl]oxymethylbenzene
• CAS: 167563-04-4
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: IVUFSPNWURFDBS-QSOAKEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((E)-(R)-1-Ethyl-hept-2-enyloxymethyl)-benzene 在 二甲基硫 、 臭氧 作用下， 生成 (+)-(R)-2-(benzyloxy)butanal
  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：

  溴甲苯 、 (R)-non-4-en-3-ol 在 sodium hydride 作用下， 生成 ((E)-(R)-1-Ethyl-hept-2-enyloxymethyl)-benzene
  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

文献信息

• Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes
  作者：Benjamin W. Gung、Jason P. Melnick、Mark A. Wolf、Amanda King

  DOI：10.1021/jo00112a012

  日期：1995.4

  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.