cis-(RS)-1-(3-chloromethyl-1,4-dioxepane-5-yl)-5-fluorouracil

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: cis-(RS)-1-(3-chloromethyl-1,4-dioxepane-5-yl)-5-fluorouracil
• 英文别名: 1-[(3R,5S)-3-(chloromethyl)-1,4-dioxepan-5-yl]-5-fluoropyrimidine-2,4-dione
• 化学式: C₁₀H₁₂ClFN₂O₄
• 分子量: 278.668
• InChiKey: RJBTVHPSUPYZOI-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 3-chloromethyl-5-methoxy-1,4-dioxepane 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以6%的产率得到trans-(RS)-1-(3-chloromethyl-1,4-dioxepane-5-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.