3-fluoro-1-phenylthiopropan-2-one | 110929-45-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-fluoro-1-phenylthiopropan-2-one
• 英文别名: 1-Fluoro-3-phenylsulfanylpropan-2-one
• CAS: 110929-45-8
• 化学式: C₉H₉FOS
• 分子量: 184.234
• InChiKey: JBLIXKJIBVXOAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-fluoro-1-phenylthiopropan-2-one 在 sodium tetrahydroborate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 2-acetoxy-1-methoxy-3-fluoropropyl phenyl sulfide
  参考文献：
  名称：

  2-酰氧基-3,3,3-三氟丙基硫醚的阳极甲氧基化伴随酰氧基的[1,2]-重排和2-(t-丁氧基羰基)氧基-3,3,3-三氟丙基硫醚的阳极环化

  摘要：

  Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides was carried out in methanol containing Et3N-3HF as a supporting electrolyte and mediator using an undivided cell to provide the corresponding alpha-methoxylated products and unexpected beta-methoxylated products owing to [1,2]-rearrangement of the acyloxy group in the latter case. It was also found that the regioselectivity and diastereoselectivity of the anodic methoxylation were greatly affected by the concentration of methanol in an electrolytic solvent, electrolytic temperature, and bulkiness of acyloxy group. This is the first example of anodic methoxylation of sulfides accompanying with rearrangement of an acyloxy group. Furthermore, anodic intramolecular cyclization of 2-(t-butoxycarbonyl)oxy-3,3,3-trifluoropropyl sulfide was achieved in 0.01 M Et3N-3HF/MeCN eliminating a t-butyl cation to provide the corresponding trifluoromethylated ethylene carbonate derivative in good yield. (c) 2017 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.1601713jes
• 作为产物：
  描述：

  氟乙酸乙酯 、 茴香硫醚 在 sec-butyllithium 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 2.0h， 以11%的产率得到3-fluoro-1-phenylthiopropan-2-one
  参考文献：
  名称：

  2-酰氧基-3,3,3-三氟丙基硫醚的阳极甲氧基化伴随酰氧基的[1,2]-重排和2-(t-丁氧基羰基)氧基-3,3,3-三氟丙基硫醚的阳极环化

  摘要：

  Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides was carried out in methanol containing Et3N-3HF as a supporting electrolyte and mediator using an undivided cell to provide the corresponding alpha-methoxylated products and unexpected beta-methoxylated products owing to [1,2]-rearrangement of the acyloxy group in the latter case. It was also found that the regioselectivity and diastereoselectivity of the anodic methoxylation were greatly affected by the concentration of methanol in an electrolytic solvent, electrolytic temperature, and bulkiness of acyloxy group. This is the first example of anodic methoxylation of sulfides accompanying with rearrangement of an acyloxy group. Furthermore, anodic intramolecular cyclization of 2-(t-butoxycarbonyl)oxy-3,3,3-trifluoropropyl sulfide was achieved in 0.01 M Et3N-3HF/MeCN eliminating a t-butyl cation to provide the corresponding trifluoromethylated ethylene carbonate derivative in good yield. (c) 2017 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.1601713jes

文献信息

• Microbial approaches to optically active sulfur-containing fluorinated compounds
  作者：Takashi Yamazaki、Masatomo Asai、Takeshi Ohnogi、Jeng Tain Lin、Tomoya Kitazume

  DOI：10.1016/s0022-1139(00)82001-1

  日期：1987.4
• YAMAZAKI TAKASHI; ASAI MASATOMO; OHNOGI TAKESHI; LIN JENQ TAIN; KITAZUME +, J. FLUOR. CHEM., 35,(1987) N 3, 537-555
  作者：YAMAZAKI TAKASHI、 ASAI MASATOMO、 OHNOGI TAKESHI、 LIN JENQ TAIN、 KITAZUME +

  DOI：——

  日期：——