2,4,6-tri-isopropylbenzeneselenol | 114964-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tri-isopropylbenzeneselenol
• 英文别名: 2,4,6-Tri(propan-2-yl)benzene-1-selenol；2,4,6-tri(propan-2-yl)benzeneselenol
• CAS: 114964-68-0
• 化学式: C₁₅H₂₄Se
• 分子量: 283.316
• InChiKey: BAIRSSBJLOJEBT-UHFFFAOYSA-N

物化性质

• 沸点：
  328.6±41.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-isopropylbenzeneselenol 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 sodium methylate 、 铜 作用下， 以 水 为溶剂， 反应 5.42h， 生成 (-)-4-(methoxycarbonyl)phenyl 2,4,6-tri-isopropylphenyl selenoxide
  参考文献：
  名称：

  Shimizu, Toshio; Kikuchi, Koichi; Ishikawa, Yoshimitsu, Journal of the Chemical Society. Perkin transactions I, 1989, p. 597 - 602

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(2,4,6-triisopropylphenyl)diselenide 在 四氟硼酸-二乙醚络合物 、 三乙基硼氢化锂 作用下， 生成 2,4,6-tri-isopropylbenzeneselenol
  参考文献：
  名称：

  Sterically hindered chalcogenolato complexes. Mono- and di-meric thiolates and selenolates of zinc and cadmium; structure of [{Cd(SeC₆H₂Bu^t₃-2,4,6)₂}₂], the first three-co-ordinate cadmium–selenium complex

  摘要：

  Protolysis of M[N(SiMe3)2]2 (M = Zn or Cd) with arenechalcogenols 2,4,6-R3C6H2EH (E = S or Se; R = Me, Pr(i) or Bu(t)) gives the corresponding chalcogenolato complexes M(EC6H2R3-2,4,6)2 in high yield. Complexes with R = Me form co-ordination polymers which are soluble only in strongly coordinating solvents. An adduct [Cd(SC6H2Me3-2,4,6)2(py)2] can be isolated which dissociates in vacuo with quantitative loss of pyridine (py). Complexes with R = Pr(i) readily dissolve in poorly coordinating solvents in which they form oligomers. NMR, infrared and Raman evidence suggests that the sterically more hindered tris-tert-butylbenzenechalcogenolato complexes of zinc and cadmium are dimeric in the solid state but dissociate in hydrocarbon solution to give two-co-ordinate monomers. The compound Zn(SeC6H2Bu(t)3-2,4,6)2 forms a 1:1 adduct with tetrahydrofuran. The structure of [{Cd(SeC6H2Bu(t)3-2,4,6)2}2] was determined by X-ray diffraction. The molecule is an asymmetrically bridged dimer, with three-co-ordinate cadmium in a distorted trigonal-planar arrangement. The Cd-Se distances are ca. 0.1 angstrom shorter than in comparable four-co-ordinate complexes.

  DOI：

  10.1039/dt9910002317

文献信息

• Synthesis of some alkyl metal selenolato complexes of zinc, cadmium and mercury. X-ray crystal structure of Me, Hg, Se(2,4,6-Pri3C62)
  作者：Manfred Bochmann、Andrew P. Coleman、Annie K. Powell

  DOI：10.1016/s0277-5387(00)83296-9

  日期：1992.1

  Abstract The metal dialkyls MR2 (M = Zn, R = Me, Et, Prn, Pri; M = Cd, R = Me) react with the sterically hindered selenol 2,4,6-Pri3C6H2SeH(Ar′SeH) under mild conditions to give the complexes [RM(SeAr′)]4, whereas the less bulky mesitylene selenol gives the poorly soluble metal bis(selenolato) complexes. MeHgNO3 reacts with Ar′SeH to give MeHg(SeAr′) whose crystal structure was determined.

  摘要金属二烷基MR2（M = Zn，R = Me，Et，Prn，Pri; M = Cd，R = Me）在温和条件下与空间受阻硒醇2,4,6-Pri3C6H2SeH（Ar'SeH）反应给出配合物[RM（SeAr'）] 4，而体积较小的均三甲苯二硒醇则得到难溶的金属双（硒代硒代）配合物。MeHgNO3与Ar'SeH反应生成MeHg（SeAr'），其晶体结构已确定。
• Diverging Effects of Steric Congestion on the Reaction of Tributylstannyl Radicals with Areneselenols and Aryl Bromides and Their Mechanistic Implications
  作者：David Crich、Jae-Taeg Hwang、Stéphane Gastaldi、Francesco Recupero、Donald J. Wink

  DOI：10.1021/jo982514a

  日期：1999.4.1

  by stannyl radicals from aryl bromides proceeds in a single step through a linear transition state whereas the abstraction of SeH from the selenols involves a T-shaped, hypervalent intermediate. Alternatively, it may be that both reactions are concerted with the bromine abstraction having a late transition state and the SeH abstraction an early one. Approximate second-order rate constants for the reaction

  研究了庞大的邻位，邻位基团对芳基溴化物和十八烯醇与三丁基锡烷反应的影响。庞大的邻，邻'基团可促进溴化物与锡烷的反应，但会延迟硒醇的反应。另一方面，从头算和力场计算表明，将大量的邻位取代基引入硒醇中比相应的溴化物引起更大的应变增加。提出了两种不同反应模式的可能解释。一方面，由苯乙烯基自由基从芳基溴化物中提取溴有可能一步一步地通过线性过渡态进行，而从硒醇中提取SeH涉及一个T形超价中间体。或者，可能这两种反应都与过渡态较晚的溴萃取和早期的SeH萃取协同进行。三丁基锡烷与一系列受阻芳基溴化物反应的近似二阶速率常数来自竞争反应。2,4,6-三叔丁基苯硒固醇能够作为锡烷介导的乙烯基溴反应的适度催化剂。提出了双（2,4,6-三异丙基苯基）二硒化物的X射线晶体结构。6-三叔丁基苯硒固醇能够作为锡烷介导的乙烯基溴反应的适度催化剂。提出了双（2,4,6-三异丙基苯基）二硒化物的X射线晶体结构。6-三叔丁基苯
• A hexanuclear copper arylselenolate: synthesis, structure and proposal for its rearrangement
  作者：Dietmar Ohlmann、Hans Pritzkow、Hansjörg Grützmacher、Mitchell Anthamatten、Rainer Glaser

  DOI：10.1039/c39950001011

  日期：——

  Copper(I) oxide reacts with selenol 2,4,6-Pri3C6H2-SeH in ethanol to give the hexanuclear copper(I) selenolate Cu[Se(2,4,6-Pri3C6H2)]}6 of 6, the solid state structure of which consists of a disordered Cu6 octahedron embedded in an antiprism formed by six selenium centres of the selenolate residues; this leads us to propose an exchange mechanism for the equilibration of all copper positions.

  氧化铜（I）与硒醇 2,4,6-Pri3C6H2-SeH 在乙醇中发生反应，生成六核硒酸铜Cu[Se(2,4,6-Pri3C6H2)]}6 的 6，其固态结构由一个无序的 Cu6 八面体组成，嵌入由硒酸铜残基的六个硒中心形成的反棱柱中。
• Sterically hindered thiolato, selenolato and tellurolato complexes of mercury(II)
  作者：Manfred Bochmann、Kevin J. Webb

  DOI：10.1039/dt9910002325

  日期：——

  Mercury(II) complexes of sterically demanding arenechalcogenolato ligands, Hg(EC6H2R3-2,4,6)2 (E = S or Se; R = Me, Pr(i) or Bu(t): E = Te; R = Me or Pr(i)) have been prepared. Whereas complexes carrying smaller aryl substituents (R = Me) are polymeric, those with R = Pr(i) and Bu(t) form linear two-co-ordinate molecules. For a given R, the volatility of the complexes increases for E = S < Se < Te, while the thermal stability decreases in the same sequence. The preferred thermal decomposition pathway is reductive elimination to metallic mercury and the corresponding diaryl dichalcogenide. The oxidative addition of diaryl ditellurides to mercury and the reverse reaction are dependent on solvent polarity and steric factors; in the case of Te this leads to an unexpected decrease in stability with increased steric hindrance of the aryl substituents, R = Me > Pr(i) >> Bu(t).
• Bochmann, Manfred; Webb, Kevin J.; Hursthouse, Michael B., Journal of the Chemical Society, Dalton Transactions
  作者：Bochmann, Manfred、Webb, Kevin J.、Hursthouse, Michael B.、Mazid, Muhammed

  DOI：——

  日期：——