2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol | 210348-33-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol
• 英文别名: 2,2-difluoro-1-phenyl-3-phenylthio-3-buten-1-ol；2,2-Difluoro-1-phenyl-3-phenylsulfanylbut-3-en-1-ol
• CAS: 210348-33-7
• 化学式: C₁₆H₁₄F₂OS
• 分子量: 292.349
• InChiKey: AFDWFHMFRBQCMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol 在 sodium amalgam 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 2-Fluoro-1-phenylhex-2-en-1-ol
  参考文献：
  名称：

  Mild allylic defluorination of 3,3-difluorobut-1-ene derivative activated by a phenylsulfonyl group

  摘要：

  4-Benzyloxy-3,3-difluoro-4-phenyl-2-phenylsulfonylbut-1-ene (3) underwent the allylic defluorination reaction with aryl- and alkylthiolate, and alkoxides without any additive reagents to give the monofluoroalkenes 4-5 in good yields. Reactions of 3 with various Grignard reagents such as alkyl-, aryl0, vinyl- and alkylethynylmagnesium bromides also provided the corresponding monofluoroalkenes 6 in good yields. Finally, compound 3 was reacted with -butylamine at -45 degrees C for 1 h to afford the monofluoroalkene 9 in good yields. (C) 2013 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2013.06.011
• 作为产物：
  描述：

  1,1,1-trifluoro-2,2-bis(phenylthio)propane 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 锌铜偶 、 偶氮二异丁腈 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol
  参考文献：
  名称：

  Allylation Of Novel β-Phenylthio Substituted gem-Difluoroallylic Bromide to Carbonyl Compounds

  摘要：

  The reaction of beta-phenylthio substituted gem-difluoroallylic bromide 3 with aldehydes and ketones in the presence of Zn(Cu) in THF at reflux temperature afforded the corresponding homoallylic alcohols 4 in good yields.

  DOI：

  10.1080/00397919908085762

文献信息

• Mild allylic defluorination of 3,3-difluorobut-1-ene derivative activated by a phenylsulfonyl group
  作者：Youn Young Hong、Ju Hee Kim、Su Jeong Choi、In Howa Jeong

  DOI：10.1016/j.jfluchem.2013.06.011

  日期：2013.11

  4-Benzyloxy-3,3-difluoro-4-phenyl-2-phenylsulfonylbut-1-ene (3) underwent the allylic defluorination reaction with aryl- and alkylthiolate, and alkoxides without any additive reagents to give the monofluoroalkenes 4-5 in good yields. Reactions of 3 with various Grignard reagents such as alkyl-, aryl0, vinyl- and alkylethynylmagnesium bromides also provided the corresponding monofluoroalkenes 6 in good yields. Finally, compound 3 was reacted with -butylamine at -45 degrees C for 1 h to afford the monofluoroalkene 9 in good yields. (C) 2013 Published by Elsevier B.V.
• Allylation Of Novel β-Phenylthio Substituted gem-Difluoroallylic Bromide to Carbonyl Compounds
  作者：In Howa Jeong、Myong Sang Kim、Bum Tae Kim

  DOI：10.1080/00397919908085762

  日期：1999.1

  The reaction of beta-phenylthio substituted gem-difluoroallylic bromide 3 with aldehydes and ketones in the presence of Zn(Cu) in THF at reflux temperature afforded the corresponding homoallylic alcohols 4 in good yields.