tetramethyl (4-methylcyclohexa-1,4-diene-1,2-diyl)bisphosphonate | 434343-03-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetramethyl (4-methylcyclohexa-1,4-diene-1,2-diyl)bisphosphonate
• 英文别名: 1,2-bis(dimethoxyphosphoryl)-4-methylcyclohexa-1,4-diene
• CAS: 434343-03-0
• 化学式: C₁₁H₂₀O₆P₂
• 分子量: 310.224
• InChiKey: DBFPGKQJDYGWJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetramethyl (4-methylcyclohexa-1,4-diene-1,2-diyl)bisphosphonate 在 五氯化磷 、 三氯氧磷 作用下， 生成 (4-methyl-o-phenylene)bis(phosphonic dichloride)
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1013931500566
• 作为产物：
  描述：

  Acetylenbis(phosphonsaeure-dimethylester) 、 天然橡胶 在 对苯二酚 作用下， 反应 6.0h， 以70%的产率得到tetramethyl (4-methylcyclohexa-1,4-diene-1,2-diyl)bisphosphonate
  参考文献：
  名称：

  A methodology for synthesis of primary o-phenylenebisphosphines and o-chlorophenylphosphines

  摘要：

  On the basis of the reaction of ethynediylbisphosphonates and chloroethynylphosphonates with classical donor alka-1,3-dienes, a general strategy for synthesis of o-bisphosphanylbenzenes and o-chlorophosphanylbenzenes, which includes two consecutive steps: Diels-Alder condensation -> aromatization of the carbocyclic phosphonate (bisphosphonate) formed -> reduction of the phosphonate groups, was developed. Convenient procedures are devised for aromatization of phosphorus-containing cyclohexa-1,4-dienes and for reduction of o-phenylenebisphosphonates and o-clorophenylphosphonates to primary phosphines. A series of new alkylsubstituted phosphonic chlorides were prepared, and a possibility of functionalization of methyl-substituted o-phenylenebisphosphonates and o-clorophenylphosphonates by the methyl groups is demonstrated.

  DOI：

  10.1134/s1070363206060089

文献信息

• Synthesis of bromine-substituted cyclohexenylphosphonates
  作者：K. S. Titov、N. I. Svintsitskaya、B. I. Ionin

  DOI：10.1134/s1070363212040068

  日期：2012.4

  Bromination of cyclohexa-1,4-dienylphosphonates yields new substituted 4,5-dibromocyclohexene-1-phosphonates. The structure of obtained compounds was confirmed by H-1, C-13 and P-31 NMR spectra.
• Epoxidation of cyclohexa-1,4-dienylphosphonates
  作者：K. S. Titov、N. I. Svintsitskaya、B. I. Ionin

  DOI：10.1134/s1070363212080245

  日期：2012.8