1-fluoro-1-(phenylthio)propan-2-one | 130612-85-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-fluoro-1-(phenylthio)propan-2-one
• 英文别名: 1-Fluoro-1-(phenylthio)-2-propanone；1-fluoro-1-phenylsulfanylpropan-2-one
• CAS: 130612-85-0
• 化学式: C₉H₉FOS
• 分子量: 184.234
• InChiKey: CBCYAUCBEBCRIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 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：

  1-fluoro-1-(phenylthio)propan-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以96%的产率得到2-丙酮,1-氟-1-(苯磺酰)-
  参考文献：
  名称：

  硫辅助串联亲电氟化脱酰：α-氟β-酮硫醚的合成

  摘要：

  首次报道了使用亲电氟化方法成功合成α-氟-β-酮硫醚。该反应通过α-亚磺酰基-β-二酮的亲电氟化反应进行，然后发生意外的串联脱酰反应。所得产物，α-氟-β-酮基硫醚，很容易被氧化成相应的α-氟-β-酮基砜，可用于进一步有用的烯化反应。

  DOI：

  10.1021/acs.joc.7b01547
• 作为产物：
  描述：

  苯硫酚 在 吡啶 、 caesium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 17.0h， 生成 1-fluoro-1-(phenylthio)propan-2-one
  参考文献：
  名称：

  硫辅助串联亲电氟化脱酰：α-氟β-酮硫醚的合成

  摘要：

  首次报道了使用亲电氟化方法成功合成α-氟-β-酮硫醚。该反应通过α-亚磺酰基-β-二酮的亲电氟化反应进行，然后发生意外的串联脱酰反应。所得产物，α-氟-β-酮基硫醚，很容易被氧化成相应的α-氟-β-酮基砜，可用于进一步有用的烯化反应。

  DOI：

  10.1021/acs.joc.7b01547

文献信息

• KI-catalyzed C–S bond formation <i>via</i> an oxidation relay strategy: efficient access to various α-thio-β-dicarbonyl compounds
  作者：Yi Jiang、Jiao-Xia Zou、Long-Tao Huang、Xue Peng、Jie-Dan Deng、Long-Qing Zhu、Yu-Hang Yang、Yi-Yue Feng、Xiao-Yun Zhang、Zhen Wang

  DOI：10.1039/c8ob00080h

  日期：——

  An efficient and practical methodology to obtain α-thio-β-dicarbonyl compounds was presented under alkaline conditions via potassium iodide (KI) catalysis.

  在碱性条件下，通过碘化钾（KI）催化，提出了一种获得α-硫代-β-二羰基化合物的高效实用方法。
• Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts
  作者：Bin Yin、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.3762/bjoc.11.12

  日期：——

  Anodic fluorination of dithioacetals bearing electron-withdrawing ester, acetyl, amide, and nitrile groups at their α-positions was comparatively studied using various supporting poly(HF) salts like Et₃N·nHF (n = 3–5) and Et₄NF·nHF (n = 3–5). In the former two cases, the corresponding α-fluorination products or fluorodesulfurization products were obtained selectively depending on supporting poly(HF) salts used. In sharp contrast, in the latter two cases, fluorination product selectivity was strongly affected by the electron-withdrawing ability of α-substituents: A dithioacetal bearing a relatively weak electron-withdrawing amide group provided a fluorodesulfurization product selectively while a dithioacetal having a strongly electron-withdrawing nitrile group gave the α-fluorination product predominantly regardless of the poly(HF) salts used.

  含有α位电子吸引酯、乙酰、酰胺和腈基团的二硫代缩醛的阳极氟化反应进行了比较研究，使用了各种支持性聚合物(HF)盐，如Et₃N·nHF (n = 3–5)和Et₄NF·nHF (n = 3–5)。在前两种情况下，根据使用的支持性聚合物(HF)盐，选择性地获得了相应的α-氟化产物或氟去硫化产物。与此形成鲜明对比的是，在后两种情况下，氟化产物的选择性受到α位取代基的电子吸引能力的强烈影响：含有相对较弱的电子吸引酰胺基团的二硫代缩醛选择性地提供氟去硫化产物，而具有强烈电子吸引腈基团的二硫代缩醛无论使用何种聚合物(HF)盐，主要产生α-氟化产物。
• Electrolytic partial fluorination of organic compounds. 1. Regioselective anodic monofluorination of organosulfur compounds
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno、Kiyono Nakagawa

  DOI：10.1021/jo00312a006

  日期：1990.12
• Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno

  DOI：10.1021/jo00116a037

  日期：1995.6

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.
• FUCHIGAMI, TOSHIO;SHIMOJO, MORIYASU;KONNO, AKINORI;NAKAGAWA, KIYONO, J. ORG. CHEM., 55,(1990) N5, C. 6074-6075
  作者：FUCHIGAMI, TOSHIO、SHIMOJO, MORIYASU、KONNO, AKINORI、NAKAGAWA, KIYONO

  DOI：——

  日期：——