Neopentyl phosphate | 7175-44-2

• 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: Neopentyl phosphate
• 英文别名: phosphoric acid mono-(2,2-dimethyl-propyl) ester；Neopentyl-dihydrogenphosphat；Neopentylphosphat；Neopentyl Dihydrogen Phosphate；2,2-dimethylpropyl dihydrogen phosphate
• CAS: 7175-44-2
• 化学式: C₅H₁₃O₄P
• 分子量: 168.13
• InChiKey: ANUKUXHGGBMTJS-UHFFFAOYSA-N

物化性质

• 沸点：
  269.2±23.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Neopentyl phosphate 、 6-Methyl-3-syn-neopentoxy-N-phenyl-2,3-oxaphosphabicyclo<2.2.2>oct-5-ene-endo-7,8-dicarboximide 3-oxide 生成 [2,2-Dimethylpropoxy(hydroxy)phosphoryl] 2,2-dimethylpropyl hydrogen phosphate
  参考文献：
  名称：

  Synthesis, fragmentation, and photorearrangement of neopentyl and adamantyl phosphonates in the 2,3-oxaphosphabicyclo[2.2.2]octene system

  摘要：

  Precursors for the generation of neopentyl and 1-adamantyl metaphosphates were prepared by the insertion of oxygen into a ring carbon-phosphorus bond of some 7-phosphanorbornene derivatives. The stereochemistry of the resulting products, which possess the 2,3-oxaphosphabicyclo[2.2.2]octene ring system, was established by NMR spectroscopy, and by X-ray analysis in one case. The O-insertion (by MCPBA) generally proceeds with retention of phosphorus configuration, but in one precursor with a syn-neopentoxy group a minor product from an inversion process was isolated. The 7-phosphanorbornene isomer with the uncommon anti neopentoxy structure was synthesized by rearrangement of the syn isomer; O-insertion gave exclusively the product of retention, identical to the minor product from the syn isomer. Conditions were developed for the photochemical fragmentation of the precursors at room temperature to release the metaphosphates; these highly reactive species were trapped as phosphates when alcohols were included in the medium. Thermal fragmentation also was effective for generating the neopentyl ester. Irradiation was also performed at -75 degrees C in an attempt to stabilize the metaphosphates so as to allow their spectral characterization, but a rearrangement occurred to give a novel tricyclic compound. In this rearrangement, the ring oxygen shifted stereospecifically to the adjacent sp(2) carbon, and a cyclopropane ring was formed.

  DOI：

  10.1021/jo00080a020
• 作为产物：
  描述：

  新戊醇 在 四丁基磷酸氢铵 、 三氯乙腈 、 ammonium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 2.0h， 以52%的产率得到Neopentyl phosphate
  参考文献：
  名称：

  One-pot synthesis of organophosphate monoesters from alcohols

  摘要：

  A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.059

文献信息

• A convenient general procedure for the conversion of alcohols into their monophosphate esters
  作者：T. A. Khwaja、C. B. Reese、J. C. M. Stewart

  DOI：10.1039/j39700002092

  日期：——

  o-Phenylene phosphorochloridate (IV), readily prepared from catechol in good yield, reacts rapidly and quantitatively with stoicheiometric amounts of alcohols (including tertiary alcohols) in the presence of a suitable base (triethylamine or 2,6-lutidine) and in a suitable solvent (dioxan, tetrahydrofuran, or benzene). Alkyl o-hydroxyphenyl phosphate salts (IX) were thus obtained in virtually quantitative

  邻苯二甲酰氯（IV）易于从邻苯二酚以高收率制得，可在合适的碱（三乙胺或2,6-二甲基吡啶）存在下，与化学计量的醇（包括叔醇）快速定量反应溶剂（二恶烷，四氢呋喃或苯）。烷基邻-羟基苯基磷酸酯盐（IX）因此以实际上定量的产率获得，有时以纯结晶化合物形式获得。
• One-pot synthesis of organophosphate monoesters from alcohols
  作者：Lucas M. Lira、Dimitar Vasilev、Ronaldo A. Pilli、Ludger A. Wessjohann

  DOI：10.1016/j.tetlet.2013.01.059

  日期：2013.3

  A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile. (c) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, fragmentation, and photorearrangement of neopentyl and adamantyl phosphonates in the 2,3-oxaphosphabicyclo[2.2.2]octene system
  作者：Louis D. Quin、Xiao-Ping Wu、Narayan D. Sadanani、Ivan Lukes、Alexey S. Ionkin、Roberta O. Day

  DOI：10.1021/jo00080a020

  日期：1994.1

  Precursors for the generation of neopentyl and 1-adamantyl metaphosphates were prepared by the insertion of oxygen into a ring carbon-phosphorus bond of some 7-phosphanorbornene derivatives. The stereochemistry of the resulting products, which possess the 2,3-oxaphosphabicyclo[2.2.2]octene ring system, was established by NMR spectroscopy, and by X-ray analysis in one case. The O-insertion (by MCPBA) generally proceeds with retention of phosphorus configuration, but in one precursor with a syn-neopentoxy group a minor product from an inversion process was isolated. The 7-phosphanorbornene isomer with the uncommon anti neopentoxy structure was synthesized by rearrangement of the syn isomer; O-insertion gave exclusively the product of retention, identical to the minor product from the syn isomer. Conditions were developed for the photochemical fragmentation of the precursors at room temperature to release the metaphosphates; these highly reactive species were trapped as phosphates when alcohols were included in the medium. Thermal fragmentation also was effective for generating the neopentyl ester. Irradiation was also performed at -75 degrees C in an attempt to stabilize the metaphosphates so as to allow their spectral characterization, but a rearrangement occurred to give a novel tricyclic compound. In this rearrangement, the ring oxygen shifted stereospecifically to the adjacent sp(2) carbon, and a cyclopropane ring was formed.