(E)-1,1-difluoro-4-(2-methoxyphenyl)-1-(phenylsulfanyl)but-3-en-2-ol | 899820-43-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1,1-difluoro-4-(2-methoxyphenyl)-1-(phenylsulfanyl)but-3-en-2-ol
• 英文别名: 1,1-difluoro-4-(2-methoxyphenyl)-1-phenylsulfanyl-3-buten-2-ol；(E)-1,1-difluoro-4-(2-methoxyphenyl)-1-phenylsulfanylbut-3-en-2-ol
• CAS: 899820-43-0
• 化学式: C₁₇H₁₆F₂O₂S
• 分子量: 322.376
• InChiKey: WORRSTKAPCOTNI-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1,1-difluoro-4-(2-methoxyphenyl)-1-(phenylsulfanyl)but-3-en-2-ol 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到1,1-difluoro-4-(2-methoxyphenyl)-1-phenylsulfinyl-3-buten-2-ol
  参考文献：
  名称：

  α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds

  摘要：

  alpha,alpha-Difluoro-alpha-phenylsulfanyl-alpha-trimethylsilylmethane (PhSCF2SiMe3) has been demonstrated as an alpha,alpha-difluoro-alpha-plhenylsulfanylmethyl carbanion equivalent. gem-Difluorophenylsulfanylmethylation of carbonyl compounds has been successfully achieved by using PhSCF2SiMe3 in the presence of TBAF in THE The adducts have been converted to the corresponding gem-difluoroalkenes by a novel pyrolytic and/or FVP elimination of the beta-hydroxy-alpha-phenyisufinyl derivatives under reduced pressure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.015
• 作为产物：
  描述：

  2-甲氧基肉桂醛 、 [二氟(苯硫基)甲基]三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到(E)-1,1-difluoro-4-(2-methoxyphenyl)-1-(phenylsulfanyl)but-3-en-2-ol
  参考文献：
  名称：

  α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds

  摘要：

  alpha,alpha-Difluoro-alpha-phenylsulfanyl-alpha-trimethylsilylmethane (PhSCF2SiMe3) has been demonstrated as an alpha,alpha-difluoro-alpha-plhenylsulfanylmethyl carbanion equivalent. gem-Difluorophenylsulfanylmethylation of carbonyl compounds has been successfully achieved by using PhSCF2SiMe3 in the presence of TBAF in THE The adducts have been converted to the corresponding gem-difluoroalkenes by a novel pyrolytic and/or FVP elimination of the beta-hydroxy-alpha-phenyisufinyl derivatives under reduced pressure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.015

文献信息

• Nucleophilic<i>gem</i>-Difluoro(phenylsulfanyl)methylation of Carbonyl Compounds with PhSCF₂H in the Presence of a Phosphazene as a Base
  作者：Teerachai Punirun、Darunee Soorukram、Chutima Kuhakarn、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1002/ejoc.201402162

  日期：2014.7

  Direct nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds has been achieved by use of difluoro(phenylsulfanyl)methane (PhSCF2H) and the phosphazene base P4-tBu in THF. Non-enolizable aldehydes and ketones are suitable substrates to undergo nucleophilic gem-difluoro(phenylsulfanyl)methylation, providing α-gem-difluoromethylated adducts in good yields. In addition, this methodology

  通过在 THF 中使用二氟（苯硫基）甲烷 (PhSCF2H) 和磷腈碱 P4-tBu，已经实现了羰基化合物的直接亲核二氟（苯硫基）甲基化。不可烯醇化的醛类和酮类是适合进行亲核钆-二氟（苯硫基）甲基化的底物，以良好的产率提供 α-gem-二氟甲基化加合物。此外，该方法也适用于环状酰亚胺和酸酐。
• α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds
  作者：Manat Pohmakotr、Kanhokthron Boonkitpattarakul、Winai Ieawsuwan、Suwatchai Jarussophon、Nongnaphat Duangdee、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/j.tet.2006.04.015

  日期：2006.6

  alpha,alpha-Difluoro-alpha-phenylsulfanyl-alpha-trimethylsilylmethane (PhSCF2SiMe3) has been demonstrated as an alpha,alpha-difluoro-alpha-plhenylsulfanylmethyl carbanion equivalent. gem-Difluorophenylsulfanylmethylation of carbonyl compounds has been successfully achieved by using PhSCF2SiMe3 in the presence of TBAF in THE The adducts have been converted to the corresponding gem-difluoroalkenes by a novel pyrolytic and/or FVP elimination of the beta-hydroxy-alpha-phenyisufinyl derivatives under reduced pressure. (c) 2006 Elsevier Ltd. All rights reserved.