(RS)-1-(1,4-oxathiepan-7-yl)-5-fluorouracil

• 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: (RS)-1-(1,4-oxathiepan-7-yl)-5-fluorouracil
• 英文别名: 5-Fluoro-1-(1,4-oxathiepan-7-yl)pyrimidine-2,4-dione
• 化学式: C₉H₁₁FN₂O₃S
• 分子量: 246.262
• InChiKey: XOAODALAFGEFBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-<2-(hydroxyethylthio)propanal> dimethyl acetal 在 三甲基氯硅烷 、 四氯化锡 、 三苯基膦 、 六甲基二硅氮烷 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 24.0h， 生成 (RS)-1-(1,4-oxathiepan-7-yl)-5-fluorouracil
  参考文献：
  名称：

  Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties

  摘要：

  A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00815-1

文献信息

• Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties
  作者：Jose A. Gómez、María A. Trujillo、Joaquín Campos、Miguel A. Gallo、Antonio Espinosa

  DOI：10.1016/s0040-4020(98)00815-1

  日期：1998.10

  A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.