di-tert-butyl 1,2-butadienylphosphonate | 131516-33-1

• 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: di-tert-butyl 1,2-butadienylphosphonate
• 英文别名: 1-[bis[(2-methylpropan-2-yl)oxy]phosphoryl]buta-1,2-diene
• CAS: 131516-33-1
• 化学式: C₁₂H₂₃O₃P
• 分子量: 246.287
• InChiKey: DGKAUXBPYRWPKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1,2-butadienylphosphonate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  Aboujaoude, Elie Elia; Collignon, Noel; Savignac, Philippe, Phosphorus and Sulfur and the Related Elements, 1983, vol. 18, p. 133 - 136

  摘要：

  DOI：
• 作为产物：
  描述：

  3-丁炔-2-醇 、 叔丁醇 在 三乙胺 、 三氯化磷 作用下， 生成 di-tert-butyl 1,2-butadienylphosphonate
  参考文献：
  名称：

  Carbanion-accelerated Claisen rearrangements. 7. Phosphine oxide and phosphonate anion stabilizing groups

  摘要：

  The utility of phosphine oxide and phosphonate groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR). Both of the groups permit the construction of substituted allyl vinyl ethers by allyl oxide addition to phosphorus-substituted allenes. Extensive optimization was required to suppress isomerization of both the allenes and the vinyl ethers. Using potassium dimsylate and lithium chloride as the base, both the phosphine oxides and phosphonates rearranged readily at room temperature with complete regioselectivity in good yield (62-93%). The phosphonates also showed a high level of diastereoselectivity (92% de). The characteristic features of the CACR were compared with the original arylsulfone version.

  DOI：

  10.1021/jo00003a021

文献信息

• Carbanion-accelerated Claisen rearrangements. 7. Phosphine oxide and phosphonate anion stabilizing groups
  作者：Scott E. Denmark、John E. Marlin

  DOI：10.1021/jo00003a021

  日期：1991.2

  The utility of phosphine oxide and phosphonate groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR). Both of the groups permit the construction of substituted allyl vinyl ethers by allyl oxide addition to phosphorus-substituted allenes. Extensive optimization was required to suppress isomerization of both the allenes and the vinyl ethers. Using potassium dimsylate and lithium chloride as the base, both the phosphine oxides and phosphonates rearranged readily at room temperature with complete regioselectivity in good yield (62-93%). The phosphonates also showed a high level of diastereoselectivity (92% de). The characteristic features of the CACR were compared with the original arylsulfone version.
• Aboujaoude, Elie Elia; Collignon, Noel; Savignac, Philippe, Phosphorus and Sulfur and the Related Elements, 1983, vol. 18, p. 133 - 136
  作者：Aboujaoude, Elie Elia、Collignon, Noel、Savignac, Philippe

  DOI：——

  日期：——