1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-5-methyl-1H,3H-pyrimidin-2,4-dione | 1257309-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-5-methyl-1H,3H-pyrimidin-2,4-dione
• CAS: 1257309-83-3
• 化学式: C₂₁H₃₃N₃O₇
• 分子量: 439.509
• InChiKey: JZFPJNVBAARSFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  128.03
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-5-methyl-1H,3H-pyrimidin-2,4-dione 在 ammonium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以74%的产率得到N-acetylserinol
  参考文献：
  名称：

  Studies on the Synthesis ofN′-Acetyl AZA-Analogues ofGanciclovir—Unexpected Liability ofN′-(2-Hydroxyethyl)-Azanucleosides Under Basic Conditions

  摘要：

  The O'-pivaloyl diesters of N'-acetyl-azanucleosides were obtained from N-[1,3-di(pivaloyloxy)prop-2-yl]-N-(pivaloyloxymethyl)acetamide and a silylated nucleobase under Vorbruggen's conditions. Unexpectedly, de-pivaloylation of the diesters under basic conditions afforded the corresponding nucleobase and N-acetylserinol. Mechanistic investigations showed that these products result from the following cascade of spontaneous transformations initiated by the mono de-pivaloylation of the starting diesters. N'-Deacetylation of the resultant mono-esters via the intramolecular N-O acetyl migration is the key step of the cascade; the corresponding NH-azanucleosides in the form of O-acetyl-O'-pivaloyl diesters are formed. Fragmentation of these diester intermediates gives the nucleobase and O-acetyl-O'-pivaloylserinol. Conversion of the latter to N-acetylserinol involves the selective O-N acetyl migration followed by de-pivaloylation of the resulting N-acetyl-O-pivaloylserinol.

  DOI：

  10.1080/15257770.2010.519367
• 作为产物：
  描述：

  三甲基乙酰氯 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 174.0h， 生成 1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-5-methyl-1H,3H-pyrimidin-2,4-dione
  参考文献：
  名称：

  Studies on the Synthesis ofN′-Acetyl AZA-Analogues ofGanciclovir—Unexpected Liability ofN′-(2-Hydroxyethyl)-Azanucleosides Under Basic Conditions

  摘要：

  The O'-pivaloyl diesters of N'-acetyl-azanucleosides were obtained from N-[1,3-di(pivaloyloxy)prop-2-yl]-N-(pivaloyloxymethyl)acetamide and a silylated nucleobase under Vorbruggen's conditions. Unexpectedly, de-pivaloylation of the diesters under basic conditions afforded the corresponding nucleobase and N-acetylserinol. Mechanistic investigations showed that these products result from the following cascade of spontaneous transformations initiated by the mono de-pivaloylation of the starting diesters. N'-Deacetylation of the resultant mono-esters via the intramolecular N-O acetyl migration is the key step of the cascade; the corresponding NH-azanucleosides in the form of O-acetyl-O'-pivaloyl diesters are formed. Fragmentation of these diester intermediates gives the nucleobase and O-acetyl-O'-pivaloylserinol. Conversion of the latter to N-acetylserinol involves the selective O-N acetyl migration followed by de-pivaloylation of the resulting N-acetyl-O-pivaloylserinol.

  DOI：

  10.1080/15257770.2010.519367