bis[2-(4-methoxyphenyl)ethyl]phosphine sulfide | 1354722-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: bis[2-(4-methoxyphenyl)ethyl]phosphine sulfide
• 英文别名: bis(4-methoxyphenethyl)phosphine sulfide
• CAS: 1354722-40-9
• 化学式: C₁₈H₂₃O₂PS
• 分子量: 334.419
• InChiKey: UITUHUYEKGNWRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  bis[2-(4-methoxyphenyl)ethyl]phosphine sulfide 在 selenium 作用下， 以 1,4-二氧六环 为溶剂， 生成 bis(4-methoxyphenethyl)phosphine sulfide
  参考文献：
  名称：

  仲膦硫化物，元素硒和乙烯基醚之间的三组分反应：马尔科夫尼科夫将硫代硒代次膦酸加成成双键的第一个例子

  摘要：

  由仲膦硫化物和元素硒原位生成的硫代次膦酸R 2 P（Se）SH容易添加到各种乙烯基醚中（等摩尔比，100°C，1,4-二恶烷，最多40分钟），可以提早提纯。未知的S-和Se- [1-（有机氧基氧基）乙基]硫代硒代次膦酸酯，即R 2 P（Se）SCH（Me）OR'和R 2 P（S）SeCH（Me）OR'（R，R'=烷基，芳烷基，杂烷基和芳基），其中S酯类占主导地位（总收率73-95％）。

  DOI：

  10.1016/j.tet.2013.05.038
• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 磷化氢 、 sulfur 作用下， 生成 bis[2-(4-methoxyphenyl)ethyl]phosphine sulfide
  参考文献：
  名称：

  通过仲硫化膦、元素硒和胺之间的三组分反应合成硫硒代次膦酸盐的新型原子经济合成

  摘要：

  通过利用仲硫化膦、元素硒和各种胺之间的三组分反应，开发了一种高效、通用且原子经济的有机铵硫代硒代次膦酸盐合成方法。该反应在温和条件（70-75°C，1 小时，乙醇）下进行，以 77-94% 的产率得到硫硒代次膦酸盐。

  DOI：

  10.1080/17415993.2011.628993

文献信息

• Electrophilic addition of thioselenophosphinic acids to vinyl sulfides and selenides
  作者：Alexander V. Artem'ev、Ludmila A. Oparina、Oksana V. Vysotskaya、Nikita A. Kolyvanov、Nina K. Gusarova、Boris A. Trofimov

  DOI：10.1080/17415993.2015.1007142

  日期：2015.3.4

  The thioselenophosphinic acids, R2P(Se)SH (R = Ph, Cy, aralkyl), prepared by acidification of the sodium salts or generated in situ by reaction of secondary phosphine sulfides with elemental selenium, add easily to diverse vinyl sulfides and vinyl selenides in a Markovnikov manner to give the corresponding S- and Se-esters in a ∼60:40 molar ratio (83–96% total yield). GRAPHICAL ABSTRACT

  硫硒代次膦酸，R2P(Se)SH（R = Ph，Cy，芳烷基），通过钠盐的酸化制备或通过仲硫化膦与元素硒的反应原位生成，很容易添加到不同的乙烯基硫化物和乙烯基硒化物中以马尔可夫尼科夫方式以~60:40的摩尔比（83-96%的总产率）给出相应的S-和Se-酯。图形概要
• Chemoselective synthesis of first representatives of bis(diorganothiophosphinyl)selenides, (R2P=S)2Se, from secondary phosphine sulfides and elemental selenium
  作者：Alexander V. Artem'ev、Ludmila A. Oparina、Nina K. Gusarova、Nikita A. Kolyvanov、Oksana V. Vysotskaya、Irina Yu. Bagryanskaya、Boris A. Trofimov

  DOI：10.1016/j.inoche.2013.01.019

  日期：2013.4

  bis(diorganothiophosphinyl)selenides, (R2P = S)2Se, have been synthesized in 74–86% yield by the chemoselective interaction of secondary phosphine sulfides with elemental selenium (1:1 molar ratio, 100 °C, 3 h, 1,4-dioxane); the alternative bis(diorganoselenophosphinyl)sulfides, (R2P = Se)2S, are not formed under these conditions.

  摘要 通过二级硫化膦与元素硒的化学选择性相互作用（1:1 摩尔比，100 °C，3 h，1 ,4-二恶烷); 在这些条件下不会形成替代的双（二有机硒代膦基）硫化物（R2P = Se）2S。
• One-pot synthesis of ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides
  作者：Nina K. Gusarova、Vladimir A. Kuimov、Svetlana F. Malysheva、Nataliya A. Belogorlova、Alexander I. Albanov、Boris A. Trofimov

  DOI：10.1016/j.tet.2012.08.091

  日期：2012.11

  Ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides have been synthesized by the exhaustive regioselective addition of secondary phosphines, phosphine sulfides and phosphine selenides to available tris(4-vinylbenzyl)phosphine oxide under free-radical conditions (UV irradiation or AIBN) in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Dual reactivity of secondary phosphines and their chalcogenides towards 1-(vinyloxy)alkylferrocenes: the switch between α- and β-addition
  作者：Alexander V. Artem'ev、Ludmila A. Oparina、Nina K. Gusarova、Oksana V. Vysotskaya、Olga A. Tarasova、Yuriy V. Gatilov、Alexander I. Albanov、Boris A. Trofimov

  DOI：10.1016/j.tet.2015.02.011

  日期：2015.4

  The secondary phosphines and their sulfides regioselectively add, under free radical conditions (AIBN, 65 degrees C or UV-irradiation, rt), to (vinyloxy)methyl- and 1-(vinyloxy)ethylferrocenes to give anti-Markov-nikov adducts in high yields. Without any initiator, the secondary phosphine selenides, when reacted with the above alkenes (rt, 24 h), selectively form Markovnikov adducts, which readily decompose upon handling to afford diorganyl[1-(ferrocenyl)alkyl]phosphine selenides, R2P(Se)CH(R')Fc (R=Ph; R'=H or Me) in 28-39% isolated yields. The synthesized compounds were characterized using H-1, C-13, P-31 NMR, and FTIR spectroscopy as well as X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.
• Superbase-Assisted Addition of Phosphine to 1-Methoxy-4-vinylbenzene: Toward a Rare Family of Organic Phosphines
  作者：S. F. Malysheva、N. K. Gusarova、A. V. Artem'ev、N. A. Belogorlova、V. I. Smirnov、V. A. Shagun、V. A. Kuimov、B. A. Trofimov

  DOI：10.1080/00397911.2010.542864

  日期：2012.6

  Phosphine reacts with 1-methoxy-4-vinylbenzene in the superbase suspension KOH-dimethylsulfoxide (70-100 degrees C, atmospheric pressure) to form regiospecifically anti-Markovnikov adducts, bis[2-(4-methoxyphenyl)ethyl]phosphine (1) and tris[2( 4-methoxyphenyl) ethyl] phosphine (2), representatives of rare arylalkylphosphines. The conditions for the selective preparation of phosphines 1 or 2 in 67% and 80% yields, respectively, have been elaborated. The phosphines have been oxidized with aqueous solution of H2O2, elemental sulfur, or selenium to afford the corresponding phosphine chalcogenides in good yields (95-99%).