1,1-Bis<<(trifluoromethanesulfonyl)oxy>methyl>cyclohexane | 169207-04-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,1-Bis<<(trifluoromethanesulfonyl)oxy>methyl>cyclohexane
• 英文别名: [1-(Trifluoromethylsulfonyloxymethyl)cyclohexyl]methyl trifluoromethanesulfonate
• CAS: 169207-04-9
• 化学式: C₁₀H₁₄F₆O₆S₂
• 分子量: 408.34
• InChiKey: WEUXOOAQQWURRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,1-Bis<<(trifluoromethanesulfonyl)oxy>methyl>cyclohexane 在 次磷酸铵 、 sodium chloride 作用下， 以 甲苯 为溶剂， 生成 2-Hydroxy-2-phosphaspiro<3.5>nonane 2-oxide
  参考文献：
  名称：

  Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids

  摘要：

  Phosphetanic, phospholanic, phosphorinanic, phosphepanic, and phosphocanic acid derivatives have been prepared in a single step by the double Arbuzov reaction of bis(trimethylsiloxy)phosphine (BTSP) with dielectrophiles. Mild, thermal reaction conditions are employed during reaction of BTSP with 1,n-dihaloalkanes (n = 3-7), a ditriflate, and omega-bromo 1,2-epoxides possessing varying levels of steric congestion and functionalization. Isolation and manipulation of pyrophoric BTSP is avoided with in situ generation of the reagent from ammonium hypophosphite and hexamethyldisilazane. Monocyclic, bicyclic, and spirocyclic phosphinic acids are obtained after purification in moderate to good isolated yields. The developed methodology is of particular interest for synthesis of nonhydrolyzable analogues of cyclic phosphodiesters.

  DOI：

  10.1021/jo00124a018
• 作为产物：
  描述：

  三氟甲磺酸酐 、 [1-(羟基甲基)环己基]甲醇 在 吡啶 作用下， 反应 2.0h， 以100%的产率得到1,1-Bis<<(trifluoromethanesulfonyl)oxy>methyl>cyclohexane
  参考文献：
  名称：

  Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids

  摘要：

  Phosphetanic, phospholanic, phosphorinanic, phosphepanic, and phosphocanic acid derivatives have been prepared in a single step by the double Arbuzov reaction of bis(trimethylsiloxy)phosphine (BTSP) with dielectrophiles. Mild, thermal reaction conditions are employed during reaction of BTSP with 1,n-dihaloalkanes (n = 3-7), a ditriflate, and omega-bromo 1,2-epoxides possessing varying levels of steric congestion and functionalization. Isolation and manipulation of pyrophoric BTSP is avoided with in situ generation of the reagent from ammonium hypophosphite and hexamethyldisilazane. Monocyclic, bicyclic, and spirocyclic phosphinic acids are obtained after purification in moderate to good isolated yields. The developed methodology is of particular interest for synthesis of nonhydrolyzable analogues of cyclic phosphodiesters.

  DOI：

  10.1021/jo00124a018

文献信息

• Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids
  作者：Jean-Luc Montchamp、Feng Tian、J. W. Frost

  DOI：10.1021/jo00124a018

  日期：1995.9

  Phosphetanic, phospholanic, phosphorinanic, phosphepanic, and phosphocanic acid derivatives have been prepared in a single step by the double Arbuzov reaction of bis(trimethylsiloxy)phosphine (BTSP) with dielectrophiles. Mild, thermal reaction conditions are employed during reaction of BTSP with 1,n-dihaloalkanes (n = 3-7), a ditriflate, and omega-bromo 1,2-epoxides possessing varying levels of steric congestion and functionalization. Isolation and manipulation of pyrophoric BTSP is avoided with in situ generation of the reagent from ammonium hypophosphite and hexamethyldisilazane. Monocyclic, bicyclic, and spirocyclic phosphinic acids are obtained after purification in moderate to good isolated yields. The developed methodology is of particular interest for synthesis of nonhydrolyzable analogues of cyclic phosphodiesters.