(R,E)-4-((oct-3-en-2-yloxy)methyl)benzene | 167563-03-3

• 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: (R,E)-4-((oct-3-en-2-yloxy)methyl)benzene
• 英文别名: [(E,2R)-oct-3-en-2-yl]oxymethylbenzene
• CAS: 167563-03-3
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: HEROUWGBBQCCPF-DNGMOHDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (R,E)-4-((oct-3-en-2-yloxy)methyl)benzene 在 二甲基硫 、 臭氧 作用下， 生成 ethyl (E,4R)-4-phenylmethoxypent-2-enoate
  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)-(E)-3-octen-2-ol 在 sodium hydride 作用下， 生成 (R,E)-4-((oct-3-en-2-yloxy)methyl)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

• Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study
  作者：Graeme Barker、David G. Johnson、Paul C. Young、Stuart A. Macgregor、Ai-Lan Lee

  DOI：10.1002/chem.201501607

  日期：2015.9.21

  necessary to ensure efficient and general chirality transfer. Computational studies suggest that the efficiency of chirality transfer is linked to the aggregation of the alcohol nucleophile around the reactive π‐bound Au–allylic ether complex. With a single alcohol nucleophile, a high degree of chirality transfer is predicted. However, if three alcohols are present, alternative proton transfer chain mechanisms

  金（I）催化的直接烯丙基醚化已成功进行手性转移，得到对映体富集的，γ取代的仲烯丙基醚。我们的研究包括完整的底物范围的筛查，以确定取代基对手性转移的区域选择性，立体选择性和效率的影响，以及控制实验，以阐明手性转移过程的机理精妙之处。至关重要的是，发现必须添加分子筛以确保有效和普遍的手性转移。计算研究表明，手性转移的效率与反应性π键金-烯丙基醚复合物周围的醇亲核试剂的聚集有关。使用单个醇亲核试剂，可以预测高度的手性转移。然而，
• 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.