Ethyl neopentyl phosphate | 143642-89-1

• 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: Ethyl neopentyl phosphate
• 英文别名: 2,2-Dimethylpropyl ethyl hydrogen phosphate；2,2-dimethylpropyl ethyl hydrogen phosphate
• CAS: 143642-89-1
• 化学式: C₇H₁₇O₄P
• 分子量: 196.183
• InChiKey: SDJCWFPXNUWIIN-UHFFFAOYSA-N

物化性质

• 沸点：
  245.0±23.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Ethyl neopentyl phosphate 生成 2,2-Dimethylpropyl ethyl methyl 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：

  2-Methyl-syn-7-neopentoxy-N-phenyl-7-phosphabicyclo<2.2.1>hept-2-ene-endo-5,6-dicarboximide 7-oxide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 48.5h， 生成 Ethyl neopentyl 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

文献信息

• A novel rearrangement reaction accompanying alkyl metaphosphate extrusion on low-temperature photolysis of 2,3-Oxaphosphabicyclo[2.2.2]octene derivatives
  作者：Louis D. Quin、Xiao-Ping Wu、Ivan Lukes、Roberta O. Day

  DOI：10.1016/0040-4039(92)88077-i

  日期：1992.7

  On photolysis in propionitrile or THF solution at −75°, three phosphonates (1-adamantyl, neopentyl, and ethyl as O-substituents) with the 2,3-oxaphosphabicyclo[2,2,2] octene ring system underwent extensive rearrangement accompanying the usual result at room temperature of metaphosphate extrusion. The rearrangement product contains a cyclopropane ring, arising from detachment of the bridgehead-bound

  在-75°下在丙腈或THF溶液中光解时，伴随有2,3-氧杂磷双环[2,2,2]辛烯环系统的三种膦酸酯（1-金刚烷基，新戊基和乙基为O-取代基）进行了广泛的重排。在室温下通常的结果是偏磷酸盐的挤出。重排产物包含环丙烷环，其由桥头结合的氧的分离，随后对双键的攻击和随后的环闭合引起。相关的磷酰胺不会发生重排，但已被氧化膦检测到。
• 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.