3,3-difluoro-1-decen-4-ol | 125982-90-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 3,3-difluoro-1-decen-4-ol
• 英文别名: 3,3-Difluorodec-1-en-4-ol
• CAS: 125982-90-3
• 化学式: C₁₀H₁₈F₂O
• 分子量: 192.249
• InChiKey: UHALJULGHVTNRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  庚醛 、 3-溴-3,3-二氟丙烯 在 锌 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到3,3-difluoro-1-decen-4-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

• A facile preparation of gem-difluorohomoallylic alcohols[1]
  作者：Zhen-Yu Yang、Donald J. Burton

  DOI：10.1016/s0022-1139(00)83950-0

  日期：1989.8
• YANG, ZHEN-YU;BURTON, DONALD J., J. FLUOR. CHEM., 44,(1989) N, C. 339-343
  作者：YANG, ZHEN-YU、BURTON, DONALD J.

  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.