2-(2-fluorophenyl)-5-phenylpent-1-en-3-ol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-(2-fluorophenyl)-5-phenylpent-1-en-3-ol
• 化学式: C₁₇H₁₇FO
• 分子量: 256.32
• InChiKey: VQKQYDRKLUPVEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  <<2-(2-fluorophenyl)-1-(2-phenylethyl)prop-2-enyl>oxy>trimethylsilane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到2-(2-fluorophenyl)-5-phenylpent-1-en-3-ol
  参考文献：
  名称：

  Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols

  摘要：

  Reactions of alpha-aryl-, alpha-heteroaryl-, and alpha-heteroatom-substituted masked alkenyllithiums with aldehydes and ketones provide a general method for the synthesis of allylic alcohols substituted with an aryl or heteroaryl in the beta position and aryl, heteroaryl or alkyl substituents in the a position via a [1,4]-C-->O silicon rearrangement. In the case of reactions with enolizable aldehydes and ketones, anhydrous CeCl3 was used as an additive. High diastereoselectivities are observed for allyl alcohols produced from a-substituted aldehydes.

  DOI：

  10.1021/jo980840k

文献信息

• Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols
  作者：Alan R. Katritzky、Dorin Toader、Xiaojing Wang

  DOI：10.1021/jo980840k

  日期：1998.12.1

  Reactions of alpha-aryl-, alpha-heteroaryl-, and alpha-heteroatom-substituted masked alkenyllithiums with aldehydes and ketones provide a general method for the synthesis of allylic alcohols substituted with an aryl or heteroaryl in the beta position and aryl, heteroaryl or alkyl substituents in the a position via a [1,4]-C-->O silicon rearrangement. In the case of reactions with enolizable aldehydes and ketones, anhydrous CeCl3 was used as an additive. High diastereoselectivities are observed for allyl alcohols produced from a-substituted aldehydes.