α-(phenylthio)isobutyrophenone | 59919-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(phenylthio)isobutyrophenone
• 英文别名: 2-methyl-1-phenyl-2-(phenylthio)propan-1-one；1-Propanone, 2-methyl-1-phenyl-2-(phenylthio)-；2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one
• CAS: 59919-11-8
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: HRAMZKSDXLCDMX-UHFFFAOYSA-N

物化性质

• 沸点：
  188-190 °C(Press: 9 Torr)
• 密度：
  1.1460 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-(phenylthio)isobutyrophenone 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 1,2-双(二苯基膦)乙烷 作用下， 以 氯苯 为溶剂， 反应 9.0h， 生成 1-苯基-2-(苯基硫代)-1-丙酮
  参考文献：
  名称：

  α-（苯硫基）异丁苯酮的铑催化杂芳族化合物的苯硫基化反应

  摘要：

  在催化量的RhH（PPh 3）4和1,2-双（二苯基膦基）乙烷（dppe）存在下，1,3-苯并噻唑，1,3-苯并恶唑和苯并噻吩与α-（苯硫基）异丁酮反应2-苯硫基衍生物。反应性单环杂芳族化合物，1-甲基-1,2,3,4-四唑和2-氰基噻吩也被转化为5-苯硫基衍生物。使用适当的苯硫基转移试剂对于将杂芳族C–H键有效催化转化为C–S键至关重要。

  DOI：

  10.1016/j.tetlet.2011.02.077
• 作为产物：
  描述：

  2-氯-2-甲基苯丙酮 在 偶氮二异丁腈 、 1,3-二甲基-2-苯基-2H-苯并咪唑 、 苯硫酚 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 以2.6%的产率得到α-(phenylthio)isobutyrophenone
  参考文献：
  名称：

  Thiophenol-promoted radical chain reduction of .alpha.-substituted isobutyrophenones by 1,3-dimethyl-2-phenylbenzimidazoline

  摘要：

  The reductions of alpha-haloacetophenones and alpha-halopropiophenones by 1,3-dimethyl-2-phenylbenzimidazoline (DMBI) have been reported to proceed via an electron-transfer free-radical chain mechanism. The reduction of alpha-haloisobutyrophenones did not proceed by the chain sequence. We now report that initiated reductions of alpha-bromo- and alpha-chloroisobutyrophenones (IIIa,b) have been found to be promoted by the addition of thiophenol. Isobutyrophenone was formed as the major product via a free-radical chain process. During the PhSH-promoted DMBI reduction of IIIa,b a minor product, alpha-(phenylthio)isobutyrophenone (IV), was also formed via nucleophilic substitution. The chain propagation steps involve the efficient hydrogen atom transfers between PhCOCMe2. and PhSH and between PhS. and DMBI. The facile hydrogen transfer between PhS. and DMBI was confirmed by carrying out the radical-chain reduction of PhSSPh with DMBI.

  DOI：

  10.1021/jo00028a048

文献信息

• Electron transfer processes. 34. Reactions of .alpha.-halo ketones with nucleophiles
  作者：Glen A. Russell、Francisco Ros

  DOI：10.1021/ja00294a050

  日期：1985.4

  On etudie les reactions des chlorures de p-nitro- ou p-cyano phenacyle ou de leurs derives dimethyl-1,1 avec divers nucleophiles

  关于对硝基苯甲酰氯苯甲酰氯苯甲酰苯甲酰氯的研究反应，衍生二甲基-1,1 avec divers 亲核试剂
• Copper‐Catalyzed Synthesis of <i>gem</i> ‐Bisarylthio Enamines under Redox‐Neutral Conditions
  作者：Jiabin Ni、Xiaokang Mao、Ao Zhang

  DOI：10.1002/adsc.201900035

  日期：2019.4.23

  An efficient approach for the construction of gem‐bisarylthio enamines via coupling of oxime acetates with diaryl disulfides is developed. This process involved copper‐catalyzed N−O/S−S bond cleavages and formation of two new C−S bonds. A broad range of substrates with diverse functional groups were tolerated.

  通过将乙酸肟与二芳基二硫化物偶合，开发了一种有效的方法来构造双芳基双烯胺。这个过程涉及铜催化的N-O / S-S键断裂和两个新的C-S键的形成。可以耐受具有各种官能团的多种底物。
• Visible light mediated reductions of ethers, amines and sulfides
  作者：Timothy M. Monos、Gabriel Magallanes、Leanne J. Sebren、Corey R.J. Stephenson

  DOI：10.1016/j.jphotochem.2016.05.014

  日期：2016.9

  Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbon–heteroatom bonds as a function of reduction potential. The expansion of the scope of C–X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of

  可见光介导的光氧化还原催化作用使活性炭-杂原子的化学选择性还原成为还原电位的函数。将C–X键还原的范围扩展至活化程度较低的基序，例如醚，胺和硫化物，对于有机合成和大分子降解方法的开发均至关重要。在本报告中，探索在醇类溶剂中进行光氧化还原催化可减少i Pr 2 NEt和HCO 2 H在超化学计量中减少α-酮醚，胺和硫化物的使用。另外，在不存在断裂的情况下，提供了C C键的形成，表明在这些转化中存在中间的酮基。
• New Syntheses of Vinyl Sulfides and Unsaturated Nitriles<i>via</i>Quaternary Phosphonium Salts
  作者：Takanobu Kumamoto、Kazuo Hosoi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.41.2742

  日期：1968.11

  of vinyl sulfides and unsaturated nitriles via quaternary phosphonium salts have been established. The reaction of isopropylidenetriphenylphosphorane with S-ethyl thiobenzoate or substituted S-ethyl thiobenzoates afforded vinyl sulfides and triphenylphosphine oxide in good yields. Further, it was found that the reaction of α-benzoylalkylphosphonium salts with sodium ethylmercaptide or potassium cyanide

  已经建立了通过季鏻盐合成乙烯基硫化物和不饱和腈的新方法。异亚丙基三苯基正膦与硫代苯甲酸 S-乙酯或取代的硫代苯甲酸 S-乙酯反应以良好的收率得到乙烯基硫化物和氧化三苯膦。此外，发现α-苯甲酰基烷基鏻盐与乙基硫醇钠或氰化钾的反应分别以良好的产率得到烯烃，例如乙烯基硫化物或不饱和腈，和氧化三苯基膦。
• Sulphurated derivatives of aromatic-aliphatic and aliphatic ketones as
  申请人：Fratelli Lamberti S.p.A.

  公开号：US05026740A1

  公开（公告）日：1991-06-25

  The invention relates to the use of a new class of sulphurated derivatives of aromatic-aliphatic or aliphatic ketones as a) polymerization or crosslinking photoinitiators for transparent or pigmented mixtures containing ethylenically unsaturated photopolymerizable compounds, in particular for obtaining polyacrylates, b) photochemically releasable latent acid catalysts, useful for crosslinking systems polycondensable by acid catalysis, of the type comprising etherified aminoplasts together with compounds containing hydroxyl, carboxyl, amido, amino and other functionalities. Said sulphurated derivatives enable manufactured articles to be obtained with exceptionally clear color while maintaining photochemical reactivity at high levels.

  本发明涉及一种新的芳基-脂肪族或脂肪基酮的硫化衍生物，作为a)聚合或交联光引发剂，用于含有乙烯基不饱和光聚合物化合物的透明或有色混合物，特别是用于获得聚丙烯酸酯；b)光化学释放的潜在酸催化剂，对酸催化下交联的聚缩醛体系有用，该体系包括醚化氨基塑料与含有羟基、羧基、酰胺基、氨基和其他官能团的化合物。所述的硫化衍生物使制造的物品在保持高水平的光化学反应性的同时，具有异常清晰的颜色。