2,5-Diphenyl-2,5-bis(selanylidene)-1,6,3,4,2lambda5,5lambda5-dioxadiselenadiphosphonane | 1034136-97-4

• 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: 2,5-Diphenyl-2,5-bis(selanylidene)-1,6,3,4,2lambda5,5lambda5-dioxadiselenadiphosphonane
• 英文别名: 2,5-diphenyl-2,5-bis(selanylidene)-1,6,3,4,2λ5,5λ5-dioxadiselenadiphosphonane
• CAS: 1034136-97-4
• 化学式: C₁₅H₁₆O₂P₂Se₄
• 分子量: 606.078
• InChiKey: CLQJTAAMHYHXOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide 、 1,3-丙二醇 以 甲苯 为溶剂， 反应 2.0h， 以51%的产率得到2-phenyl-1,3,2-dioxaphosphorinane-2-selenide
  参考文献：
  名称：

  New P–Se compounds from the reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide with alkyl-diols

  摘要：

  Reaction of alkyl-diols [HO(CH2)(n)OH, n=2-6, 8 and 10] with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [(PhP(mu-Se)Se)(2) Woollins' reagent, WR] in dry dichloromethane gave a series of bisdiselenophosphonic acids at room temperature. Treatment of the acids with butylamine in tetrahydrofuran afforded the corresponding ammonium salts 1-7 in excellent yields (91-97%). Esterification of the salts with methyl iodide led to Se,Se-dimethyl esters 8-14 in medium to excellent yields (50-86%). Alternatively, heating the toluene solution of alkyl-diols [HO(CH2)(n)OH, n-2-4] and WR at reflux, afforded 1,3,2-dioxaphosphorinane-2-phenyl-2-selenides 16, 18 and 20 in reasonable to good yield. Meanwhile, when 1,2-ethylene glycol was used, a heterocycle containing a selenium atom, 2,4-bisphenyl-2,4-diseleno-1,5dioxa-3-seleno-2,4-diphosphetane 15 was formed. In the case of 1,3-propanediol or 1,4-butanediol, the heterocycles containing two neighbouring selenium atoms, 2,5-diphenyl-(1,6,3,4,2,5)-dioxadiselenadiphosphocane-2,5-disulfides 17 and 19 were obtained together with 18 and 20. Perhaps due to a steric effect, pinacol and WR in toluene at reflux gave 1,3,2-dioxapbosphorinane-2-selenide 21 as the only product. One representative X-ray crystal structure of an ammonium salt is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.017

文献信息

• New P–Se compounds from the reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide with alkyl-diols
  作者：Guoxiong Hua、Yang Li、Alexandra M.Z. Slawin、J. Derek Woollins

  DOI：10.1016/j.tet.2008.04.017

  日期：2008.6

  Reaction of alkyl-diols [HO(CH2)(n)OH, n=2-6, 8 and 10] with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [(PhP(mu-Se)Se)(2) Woollins' reagent, WR] in dry dichloromethane gave a series of bisdiselenophosphonic acids at room temperature. Treatment of the acids with butylamine in tetrahydrofuran afforded the corresponding ammonium salts 1-7 in excellent yields (91-97%). Esterification of the salts with methyl iodide led to Se,Se-dimethyl esters 8-14 in medium to excellent yields (50-86%). Alternatively, heating the toluene solution of alkyl-diols [HO(CH2)(n)OH, n-2-4] and WR at reflux, afforded 1,3,2-dioxaphosphorinane-2-phenyl-2-selenides 16, 18 and 20 in reasonable to good yield. Meanwhile, when 1,2-ethylene glycol was used, a heterocycle containing a selenium atom, 2,4-bisphenyl-2,4-diseleno-1,5dioxa-3-seleno-2,4-diphosphetane 15 was formed. In the case of 1,3-propanediol or 1,4-butanediol, the heterocycles containing two neighbouring selenium atoms, 2,5-diphenyl-(1,6,3,4,2,5)-dioxadiselenadiphosphocane-2,5-disulfides 17 and 19 were obtained together with 18 and 20. Perhaps due to a steric effect, pinacol and WR in toluene at reflux gave 1,3,2-dioxapbosphorinane-2-selenide 21 as the only product. One representative X-ray crystal structure of an ammonium salt is described. (C) 2008 Elsevier Ltd. All rights reserved.