4,4-difluoro-2-phenyl-5-hexen-3-ol | 131437-08-6

• 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: 4,4-difluoro-2-phenyl-5-hexen-3-ol
• 英文别名: 4,4-Difluoro-2-phenylhex-5-en-3-ol
• CAS: 131437-08-6
• 化学式: C₁₂H₁₄F₂O
• 分子量: 212.239
• InChiKey: ADJQKULXQQSZKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  306.6±42.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-3,3-二氟丙烯 、 2-苯基丙醛 在 锌 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到4,4-difluoro-2-phenyl-5-hexen-3-ol
  参考文献：
  名称：

  Gem-difluoroallylation of aldehydes and ketones as a convenient route to .alpha.,.alpha.-difluorohomoallylic alcohols

  摘要：

  In the presence of zinc, 3-bromo-3,3-difluoropropene or 3-iodo-1,1-difluoropropene reacted with carbonyl compounds to give the corresponding alpha,alpha-difluorohomoallylic alcohols in good yields at 0-degrees-C to room temperature. The reaction is applicable to aliphatic and aromatic aldehydes, dialkyl ketones, and alkyl aryl ketones. Reaction with alpha,beta-unsaturated aldehydes and ketones yielded 1,2-adducts exclusively. However, the reaction could not be extended to esters and acyl chlorides. Other metals such as cadmium and tin could also be used to mediate gem-difluoroallylation. The regiochemistry of this reaction could be rationalized in terms of the more nucleophilic alpha-carbon of the gem-difluoroallyl intermediate.

  DOI：

  10.1021/jo00003a025

文献信息

• FUJITA, MAKOTO;OBAYASHI, MICHIO;HIYAMA, TAMEJIRO, TETRAHEDRON, 44,(1988) N 13, C. 4135-4145
  作者：FUJITA, MAKOTO、OBAYASHI, MICHIO、HIYAMA, TAMEJIRO

  DOI：——

  日期：——
• Gem-difluoroallylation of aldehydes and ketones as a convenient route to .alpha.,.alpha.-difluorohomoallylic alcohols
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00003a025

  日期：1991.2

  In the presence of zinc, 3-bromo-3,3-difluoropropene or 3-iodo-1,1-difluoropropene reacted with carbonyl compounds to give the corresponding alpha,alpha-difluorohomoallylic alcohols in good yields at 0-degrees-C to room temperature. The reaction is applicable to aliphatic and aromatic aldehydes, dialkyl ketones, and alkyl aryl ketones. Reaction with alpha,beta-unsaturated aldehydes and ketones yielded 1,2-adducts exclusively. However, the reaction could not be extended to esters and acyl chlorides. Other metals such as cadmium and tin could also be used to mediate gem-difluoroallylation. The regiochemistry of this reaction could be rationalized in terms of the more nucleophilic alpha-carbon of the gem-difluoroallyl intermediate.