O,O-diethyl S-(3-oxo-1,3-diphenylpropyl)phosphorodithioate | 79359-70-9

• 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: O,O-diethyl S-(3-oxo-1,3-diphenylpropyl)phosphorodithioate
• 英文别名: 3-Diethoxyphosphinothioylsulfanyl-1,3-diphenylpropan-1-one
• CAS: 79359-70-9
• 化学式: C₁₉H₂₃O₃PS₂
• 分子量: 394.496
• InChiKey: KWZZWGMFQZXKTN-UHFFFAOYSA-N

物化性质

• 沸点：
  510.4±60.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O,O-diethyl S-(3-oxo-1,3-diphenylpropyl)phosphorodithioate 、 乙硫醇钠 反应 0.07h， 以77%的产率得到(2S,4S)-2-ethylsulfanyl-2,4-diphenylthietane
  参考文献：
  名称：

  通过 O,O-二乙基 S-(1,3-二芳基-3-氧代丙基)二硫代磷酸酯的亲核诱导环化快速无溶剂合成功能化硫杂环丁烷

  摘要：

  通过亲核试剂 (CN - , RS - ) 诱导 O,O-二乙基 S-(1报道了在无溶剂条件下微波照射下的 ,3-diaryl-3-oxopropyl)phosphorodithioates 3a-c。

  DOI：

  10.1055/s-2002-33337
• 作为产物：
  描述：

  （2Z）-1,3-二苯基-2-丙烯-1-酮，2-丙烯-1-酮，1,3-二苯基-，（2Z）- 、 二硫代磷酸二乙酯 在 1-甲基-3-戊基溴化咪唑 作用下， 反应 0.75h， 以93%的产率得到O,O-diethyl S-(3-oxo-1,3-diphenylpropyl)phosphorodithioate
  参考文献：
  名称：

  Catalysis by ionic liquid: a simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br

  摘要：

  A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as alpha,beta-unsaturated carbonyl compounds, carboxylic esters, nitriles and chalcones without requiring any other organic solvent and catalyst. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.052

文献信息

• Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade
  作者：Fang Li、David Calabrese、Matthew Brichacek、Ivy Lin、Jon T. Njardarson

  DOI：10.1002/anie.201108261

  日期：2012.2.20

  The fifth element: An efficient new synthetic method for accessing 3,6‐dihydro‐2H‐thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates

  第五要素：开发了一种有效的新型合成方法，可在一锅中获得3,6-dihydro-2 H - thiopyrans 1。该方法采用阴离子级联，其通过将乙烯基亲核试剂加到羰基上，然后硫代磷酸酯从S到O的迁移和分子内硫醇盐的置换来触发。该范围适用于各种酮和酯底物。
• A Convenient Synthesis of 2,4-Diarylthietanes by Reductive Cyclization of<i>O,O</i>-Diethyl<i>S</i>-(1,3-Diaryl-3-oxopropyl) Phosphorodithioates
  作者：Yoshio Ueno、L. D. S. Yadav、Makoto Okawara

  DOI：10.1055/s-1981-29521

  日期：——
• Catalysis by ionic liquid: a simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br
  作者：Brindaban C Ranu、Suvendu S Dey

  DOI：10.1016/j.tet.2004.03.052

  日期：2004.5

  A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as alpha,beta-unsaturated carbonyl compounds, carboxylic esters, nitriles and chalcones without requiring any other organic solvent and catalyst. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.
• An Expeditious Solvent Free Synthesis of Functionalised Thietanes by Nucleophile-Induced Cyclisation of<i>O</i>,<i>O</i>-Diethyl<i>S</i>-(1,3-Diaryl-3-oxopropyl) Phosphorodithioates
  作者：Lal Dhar Yadav、Ritu Kapoor

  DOI：10.1055/s-2002-33337

  日期：——

  An expeditious and highly diastereoselective synthesis of (Z)-2-alkylsulfenyl(or 2-cyano)-2,4-diarylthietanes 5a-i by nucleophile (CN - , RS - ) induced cyclisation of O,O-diethyl S-(1,3-diaryl-3-oxopropyl) phosphorodithioates 3a-c under microwave irradiation in solvent free conditions is reported.

  通过亲核试剂 (CN - , RS - ) 诱导 O,O-二乙基 S-(1报道了在无溶剂条件下微波照射下的 ,3-diaryl-3-oxopropyl)phosphorodithioates 3a-c。