1,3-diphenyl-3-(4-fluorophenylsulfanyl)propan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-diphenyl-3-(4-fluorophenylsulfanyl)propan-1-one
• 英文别名: 3-(4-fluorophenylsulfanyl)-1,3-diphenylpropan-1-one；3-(4-fluorophenylthio)-1,3-diphenylpropane-1-one；3-(4-Fluorophenyl)sulfanyl-1,3-diphenylpropan-1-one
• 化学式: C₂₁H₁₇FOS
• 分子量: 336.43
• InChiKey: KXCQXLZOUJAHTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.16h， 生成 1,3-diphenyl-3-(4-fluorophenylsulfanyl)propan-1-one
  参考文献：
  名称：

  基于间接阳离子池法的硫离子的生成、表征和反应

  摘要：

  PhCH=S+Ar (Ar = p-FC6H4) 首次在二氯甲烷等有机合成常用的有机溶剂中通过间接阳离子池法产生并积累...

  DOI：

  10.1246/bcsj.20150323

文献信息

• L-Proline Catalyzed Michael Additions of Thiophenols to α,β-Unsaturated Compounds, Particularly α-Enones, in the Ionic Liquid [bmim]PF6
  作者：Peter Kotrusz、Stefan Toma

  DOI：10.3390/11020197

  日期：——

  L-proline catalyzed additions of 13 different thiols to 11 different alpha-enone Michael acceptors in [bmim] PF(6 )are reported. Reasonable to high yields of the reaction products were isolated in most cases.

  据报道，L-脯氨酸催化了 [bmim] PF(6) 中 13 种不同硫醇与 11 种不同 α-烯酮迈克尔受体的添加。在大多数情况下分离出合理到高产率的反应产物。
• Michael addition of thiols to α-enones in ionic liquids with and without organocatalysts
  作者：Mária Mečiarová、Štefan Toma、Peter Kotrusz

  DOI：10.1039/b516289k

  日期：——

  Seventeen organocatalyts were tested for their ability to catalyst the addition of thiophenols to chalcones in [bmim]PF6. The products were isolated in high yield after a short reaction time, but no stereoselectivity was observed. The reactions also proceeded (without any stereoselectivity) in four other ionic liquids. In contrast, 16% and 26% ee were observed when L-proline and cinchonine, respectively, were used as the catalysts in CH2Cl2. Addition of thiophenols is also catalysed by HCl, as well as D-mandelic and L-tartaric acids. Addition of thiophenols to chalcones also occurred in neat ionic liquids, without any additional catalyst, but the rate of the reaction depended considerably on the structure of ionic liquid. The scope of the non-catalysed reaction in ionic liquids was tested by the reactions of 5 different thiols and 3 different α-enones.

  在[bmim]PF6中，测试了十七种有机催化剂对噻吩醇与查尔酮加成反应的催化能力。产物在短反应时间内以高收率分离，但未观察到立体选择性。该反应在其他四种离子液体中也进行（没有立体选择性）。相比之下，在CH2Cl2中分别使用L-脯氨酸和辛可宁作为催化剂时，观察到了16%和26%的ee值。噻吩醇的加成反应也受HCl、D-扁桃酸和L-酒石酸的催化。噻吩醇与查尔酮的加成反应在没有额外催化剂的情况下也在纯净的离子液体中发生，但反应速率很大程度上取决于离子液体的结构。通过5种不同的硫醇与3种不同的α-烯酮的反应，测试了离子液体中非催化反应的范围。
• Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds
  作者：Xi Huang、Juan Li、Xiang Li、Jiayi Wang、Yanqing Peng、Gonghua Song

  DOI：10.1039/c9ra05708k

  日期：——

  A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α- or β-position of carbonyls with different sulfur reagents under slightly changed reaction conditions. A series of desired products were obtained in moderate

  开发了一种新颖、高效、无催化剂且产物可控的策略，用于 α,β-不饱和羰基化合物的化学选择性 α-磺基化/β-硫醇化。在稍微改变反应条件下，可以使用不同的硫试剂在羰基的α-或β-位上化学选择性地引入芳香族硫基团。以中等至优异的收率获得了一系列所需的产物。机理研究表明，B 2 pin 2在激活α,β-不饱和羰基化合物向β-硫醇化转变中发挥关键作用。这种无过渡金属催化剂的方法为α,β-不饱和羰基化合物的α-硫醇化或β-磺酰化产物的高度化学选择性制备提供了便捷有效的工具。