di-tert-butyl isobutyl phosphate | 68695-43-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: di-tert-butyl isobutyl phosphate
• 英文别名: Isobutyl-di-t-butylphosphat；phosphoric acid di-tert-butyl ester isobutyl ester；Di-tert-butyl 2-methylpropyl phosphate；ditert-butyl 2-methylpropyl phosphate
• CAS: 68695-43-2
• 化学式: C₁₂H₂₇O₄P
• 分子量: 266.318
• InChiKey: DMHCJPOSLXIEJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-tert-butyl isobutyl phosphate 在 四甲基乙二胺 、 仲丁基锂 、 溶剂黄146 作用下， 以 正己烷 为溶剂， 反应 26.0h， 以45%的产率得到膦酸,(1-羟基-2-甲基丙基)-,二(1,1-二甲基乙基)酯
  参考文献：
  名称：

  THE PHOSPHATE-PHOSPHONATE AND PHOSPHONATE-PHOSPHATE REARRANGEMENTS AND THEIR APPLICATIONS - 7[1]: USE OF t-BUTYL AS PROTECTING GROUP AND SYNTHESIS OF CHIRAL, NONRACEMIC α-HYDROXYPHOSPHONATES

  摘要：

  The regioselectivity of metallation of hexyl diisopropyl phosphate (1) depends oil the solvent, the temperature, and the base used. The best results are obtained with s-BuLi/TMEDA in hexane and diethyl ether at -78 degreesC, the CH2O group being deprotonated preferentially over the CHO group (3:1 versus 2.5:1). The intermediate phosphonyloxy-substituted alkyllithiums (+/-)-4 and (+/-)-5 rearrange to phosphonates (+/-)-6 and (+/-)-7, respectively. The isopropyl groups can be replaced by t-butyl groups to direct metallation exclusively to CH2O. Homochiral diamines in place of TMEDA give chiral, nonracemic alpha -hydroxyphosphonates.

  DOI：

  10.1080/10426500108040236
• 作为产物：
  描述：

  potassium di-tert-butylphosphate 以 乙二醇二甲醚 为溶剂， 生成 di-tert-butyl isobutyl phosphate
  参考文献：
  名称：

  Tetra-n-butylaminium Di-t-butyl Phosphate. A New, Effective Phosphorylating Agent for Alkyl Bromides

  摘要：

  DOI：

  10.1055/s-1978-24887

文献信息

• Di-<i>tert</i>-butyl<i>N,N</i>-Diethylphosphoramidite. A New Phosphitylating Agent for the Efficient Phosphorylation of Alcohols
  作者：John W. Perich、R. B. Johns

  DOI：10.1055/s-1988-27494

  日期：——

  Alkyl and aryl di-tert-butyl phosphates were prepared in high yields by the 1H-tetrazole-promoted phosphitylation of alkyl and aryl alcohols with di-tert-butyl N,N-diethylphosphoramidite, followed by oxidation of the resultant alkyl and aryl di-tert-butyl phosphite triesters with m-chloroperoxybenzoic acid.

  用 N,N-二乙基二叔丁基亚磷酰胺对烷基和芳基醇进行 1H-四唑促进的磷酸化反应，然后用间氯过氧苯甲酸氧化生成的烷基和芳基二叔丁基亚磷酸三酯，从而制备出高产率的烷基和芳基二叔丁基磷酸盐。
• THE PHOSPHATE-PHOSPHONATE AND PHOSPHONATE-PHOSPHATE REARRANGEMENTS AND THEIR APPLICATIONS - 7[1]: USE OF <i>t</i>-BUTYL AS PROTECTING GROUP AND SYNTHESIS OF CHIRAL, NONRACEMIC α-HYDROXYPHOSPHONATES
  作者：Friedrich Hammerschmidt、Susanne Schmidt

  DOI：10.1080/10426500108040236

  日期：2001.8.1

  The regioselectivity of metallation of hexyl diisopropyl phosphate (1) depends oil the solvent, the temperature, and the base used. The best results are obtained with s-BuLi/TMEDA in hexane and diethyl ether at -78 degreesC, the CH2O group being deprotonated preferentially over the CHO group (3:1 versus 2.5:1). The intermediate phosphonyloxy-substituted alkyllithiums (+/-)-4 and (+/-)-5 rearrange to phosphonates (+/-)-6 and (+/-)-7, respectively. The isopropyl groups can be replaced by t-butyl groups to direct metallation exclusively to CH2O. Homochiral diamines in place of TMEDA give chiral, nonracemic alpha -hydroxyphosphonates.
• Tetra-<i>n</i>-butylaminium Di-<i>t</i>-butyl Phosphate. A New, Effective Phosphorylating Agent for Alkyl Bromides
  作者：Maria KLUBA、Andrzej ZWIERZAK

  DOI：10.1055/s-1978-24887

  日期：——