4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol | 736137-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol
• 英文别名: 4-Methyl-2-(5-methyl-2-sulfanylphenyl)phosphanylbenzenethiol
• CAS: 736137-64-7
• 化学式: C₁₄H₁₅PS₂
• 分子量: 278.379
• InChiKey: NECCAUGEYXNMHX-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 0.5 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol 在 三氯化磷 作用下， 生成 cis-2,10-dimethyl<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole
  参考文献：
  名称：

  三种不同C-P键的高度原子经济一键形成：无环叔膦硫化物的一般合成

  摘要：

  苯并噻二磷1与R 1 MgBr和R 2 MgBr的等摩尔混合物反应生成中间体A '，仅在4-5分钟后，用等摩尔量的R 3 MgBr处理中间体A ' ，得到不对称膦PR 1 R 2 R 3占总产率的45％（当R 1 = R 2时产率为75-80％，当R 1 = R 2 = R 3时产率为85-90％），副产物6的产率为90％。用PCl 3处理6可定量再生起始试剂1。用元素硫处理膦，得到相应的硫化物。

  DOI：

  10.1021/jo0502145
• 作为产物：
  描述：

  cis-2,10-dimethyl<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole 在 (butane-1,4-diyl)dimagnesium dibromide 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol
  参考文献：
  名称：

  高效一锅合成仲环状膦，并易于再生所用的磷供体试剂。

  摘要：

  DOI：

  10.1002/anie.200453820

文献信息

• The First Flights of a Molecular Shuttle Transporting Elements: Easy One-pot Formation of Organic Cyclic Arsanes, Stibanes and Bismutanes
  作者：Graziano Baccolini、Carla Boga、Marzia Mazzacurati、Gabriele Micheletti

  DOI：10.1002/chem.200802007

  日期：2009.1.5

  Maiden voyage: New arsenic‐, antimony‐ and bismuth‐donor reagents (1 b–d) are used in a one‐pot synthesis of cyclic arsanes, stibanes and bismutanes through a procedure in which the simultaneous formation of three CAs, CSb or CBi bonds is achieved. At the end of the reaction, the element‐donor reagent can be easily re‐formed “in situ” and recycled, as in a catalytic process.

  处女航次：一种新的砷，锑和铋供体试剂（1 b – d）通过一种同时合成三个C rs As，C的方法，用于一锅合成环状a烷，二苯乙烯和双变烷获得Sb或CBi键。在反应结束时，可以像在催化过程中一样轻松地“原位”重组元素供体试剂并回收利用。
• Identification of a four-center intermediate in a Grignard addition reaction to a P–S bond
  作者：Graziano Baccolini、Carla Boga、Marzia Mazzacurati

  DOI：10.1016/j.tet.2007.10.015

  日期：2007.12

  The reaction between tert-butylmagnesium chloride (or tert-pentyl magnesium chloride) and the particular phosphorus-sulfur bond of a benzothiadiphospholic system showed, for the first time, evidence of formation of intermediates with a four-center structure. The possibility, for the phosphorus atom, to have very stable hypervalent coordinations makes it possible to observe its hypervalent states during the course of a reaction. The benzothiadiphosphole, with its bicyclic folded structure, further stabilizes the hypervalent coordinations thus making the intermediates sufficiently stable to be detected during the course of the reaction by P-31 NMR spectroscopy, which revealed the nature and the stability of the species involved in this reaction, carried out also using other Grignard reagents. (c) 2007 Elsevier Ltd. All rights reserved.
• Highly Atom-Economic One-Pot Formation of Three Different C−P Bonds:  General Synthesis of Acyclic Tertiary Phosphine Sulfides
  作者：Graziano Baccolini、Carla Boga、Marzia Mazzacurati

  DOI：10.1021/jo0502145

  日期：2005.6.1

  4−5 min, was treated with an equimolar amount of R3MgBr, giving the asymmetric phosphine PR1R2R3 in 45% overall yield (75−80% yield when R1 = R2 and 85−90% yield when R1 = R2 = R3) and the byproduct 6 in 90% yield. The treatment of 6 with PCl3 quantitatively regenerates the starting reagent 1. Treatment of the phosphines with elemental sulfur gave the corresponding sulfides.

  苯并噻二磷1与R 1 MgBr和R 2 MgBr的等摩尔混合物反应生成中间体A '，仅在4-5分钟后，用等摩尔量的R 3 MgBr处理中间体A ' ，得到不对称膦PR 1 R 2 R 3占总产率的45％（当R 1 = R 2时产率为75-80％，当R 1 = R 2 = R 3时产率为85-90％），副产物6的产率为90％。用PCl 3处理6可定量再生起始试剂1。用元素硫处理膦，得到相应的硫化物。
• Efficient One-Pot Synthesis of Secondary Cyclic Phosphanes with Easy Regeneration of the Phosphorus-Donor Reagent Used
  作者：Graziano Baccolini、Carla Boga、Matteo Galeotti

  DOI：10.1002/anie.200453820

  日期：2004.6.7