(+/-)-2-O--2'-cyclohexenyl>thymine

• 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: (+/-)-2-O--2'-cyclohexenyl>thymine
• 英文别名: 2-[(1R,4S)-4-[di(propan-2-yloxy)phosphorylmethoxy]cyclohex-2-en-1-yl]oxy-5-methyl-1H-pyrimidin-6-one
• 化学式: C₁₈H₂₉N₂O₆P
• 分子量: 400.412
• InChiKey: BOAABTVRRZJUAL-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (二异丙氧基磷酰)甲基对甲苯磺酸酯 在 氨 、 sodium hydride 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (+/-)-2-O--2'-cyclohexenyl>thymine
  参考文献：
  名称：

  Application of the Mitsunobu-Type Condensation Reaction to the Synthesis of Phosphonate Derivatives of Cyclohexenyl and Cyclohexanyl Nucleosides

  摘要：

  1,4-trans-cyclohexanediol has been used as starting material for the synthesis of cyclohexenyl and cyclohexanyl nucleosides functionalized with a OCH2P(O)(OH)(2) moiety in a 1,4-cis relationship with the heterocyclic base. The methodology used is based on the Mitsunobu-type condensation of a conveniently functionalized alcohol with both purines and pyrimidines bases. In all cases (except for cytosine) the natural substituted derivative (N-9 for purines and N-1 for pyrimidines) were obtained as the major isomers. The N-1 cytosine derivative was thus obtained from its uracil analogue. Yields were higher when an allylic alcohol was used in the condensation. Far this reason, cyclohexanyl nucleosides were obtained from their cyclohexenyl analogues by reduction of the 2',3'-double bond. The phosphonomethoxy moiety was introduced prior to the coupling with the heterocyclic base to avoid protection or undesired alkylations of the bases during the derivatization of the 4'-alcohol function.

  DOI：

  10.1021/jo00111a010

文献信息

• Application of the Mitsunobu-Type Condensation Reaction to the Synthesis of Phosphonate Derivatives of Cyclohexenyl and Cyclohexanyl Nucleosides
  作者：Maria-Jesus Perez-Perez、Jef Rozenski、Roger Busson、Piet Herdewijn

  DOI：10.1021/jo00111a010

  日期：1995.3

  1,4-trans-cyclohexanediol has been used as starting material for the synthesis of cyclohexenyl and cyclohexanyl nucleosides functionalized with a OCH2P(O)(OH)(2) moiety in a 1,4-cis relationship with the heterocyclic base. The methodology used is based on the Mitsunobu-type condensation of a conveniently functionalized alcohol with both purines and pyrimidines bases. In all cases (except for cytosine) the natural substituted derivative (N-9 for purines and N-1 for pyrimidines) were obtained as the major isomers. The N-1 cytosine derivative was thus obtained from its uracil analogue. Yields were higher when an allylic alcohol was used in the condensation. Far this reason, cyclohexanyl nucleosides were obtained from their cyclohexenyl analogues by reduction of the 2',3'-double bond. The phosphonomethoxy moiety was introduced prior to the coupling with the heterocyclic base to avoid protection or undesired alkylations of the bases during the derivatization of the 4'-alcohol function.