diethyl [4-(tert-butylsulfanyl)benzyl]phosphonate | 500530-72-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: diethyl [4-(tert-butylsulfanyl)benzyl]phosphonate
• 英文别名: diethyl 4-(tert-butylthio)benzylphosphonate；(4-(t-Butylsulfanyl)-benzyl)-phosphonic acid diethyl ester；1-tert-butylsulfanyl-4-(diethoxyphosphorylmethyl)benzene
• CAS: 500530-72-3
• 化学式: C₁₅H₂₅O₃PS
• 分子量: 316.401
• InChiKey: JGJRRKHUUMHRLI-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±38.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl [4-(tert-butylsulfanyl)benzyl]phosphonate 在 potassium tert-butylate 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 1-[4-(acetylthio)styryl]-3-acetylpyrene
  参考文献：
  名称：

  Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

  摘要：

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

  DOI：

  10.1021/jo0263770
• 作为产物：
  描述：

  4-(叔丁基磺酰基)苯甲醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 反应 14.0h， 生成 diethyl [4-(tert-butylsulfanyl)benzyl]phosphonate
  参考文献：
  名称：

  Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

  摘要：

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

  DOI：

  10.1021/jo0263770

文献信息

• Synthesis, UV/vis spectra and electrochemical characterisation of arylthio and styryl substituted ferrocenes
  作者：Thomas Sørensen、Merete Nielsen

  DOI：10.2478/s11532-011-0040-8

  日期：2011.8.1

  AbstractTwo series of substituted ferrocenes were synthesised using either the Horner-Wadsworth-Emmons reaction or monolithiation of ferrocene. The series consist of arylthio- and styryl-ferrocenes with different substituents in the para position of the aryl rings of the systems. The electronic communication was investigated by comparing the substituent effects in absorption spectroscopy and in cyclic

  摘要 利用Horner-Wadsworth-Emmons反应或二茂铁单锂化合成了两个系列的取代二茂铁。该系列由芳硫基和苯乙烯基二茂铁组成，在系统芳环的对位具有不同的取代基。通过比较吸收光谱和循环伏安法中的取代基效应来研究电子通讯。在苯乙烯基取代的二茂铁的电子跃迁中发现了小的取代效应。二茂铁衍生物的氧化显示出明显的取代效应，如线性哈米特图所示。芳硫基系统中的效果显示出比苯乙烯基系统大一个数量级。有人认为，大效应背后的原因是硫铁轨道直接重叠。
• The synthesis of π-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core unit and sulfur alligator clips
  作者：Arnošt Seidler、Jiří Svoboda、Václav Dekoj、Jana Vacek Chocholoušová、Jaroslav Vacek、Irena G. Stará、Ivo Starý

  DOI：10.1016/j.tetlet.2013.03.084

  日期：2013.5

  A series of short oligo(p-phenylene-ethynylene)- and oligo(p-phenylenevinylene)-type molecular rods with an electronically rich thiophene or thieno[3,2-b]thiophene core unit and sulfur anchoring groups (AcS-, t-BuS-) at the termini have been synthesised using Sonogashira coupling or Homer-Wads-worth-Emmons (E)-olefination methodology. The collection of linear/bent, conjugated/cross-conjugated systems has been characterised by UV-vis and fluorescence spectroscopy, optical/calculated HOMO-LUMO gaps and calculated excitation energies. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)
  作者：Nicolai Stuhr-Hansen、Jørn B. Christensen、Niels Harrit、Thomas Bjørnholm

  DOI：10.1021/jo0263770

  日期：2003.2.1

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.