6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one | 900806-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one
• 英文别名: 6-hydroxymethylfuro[2,3-d]pyrimidin-2-one；6-(hydroxymethyl)-1H-furo[2,3-d]pyrimidin-2-one
• CAS: 900806-61-3
• 化学式: C₇H₆N₂O₃
• 分子量: 166.136
• InChiKey: QKUORMNQOZKRCD-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C (decomp)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one 在 吡啶 、 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 6-(chloromethyl)-3-dodecylfuro[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  Synthesis of 6-(alkoxymethyl)- and 6-(alkylsulfanylmethyl)furo[2,3-d]pyrimidin-2(3H)-one analogues

  摘要：

  用 1-iodoalkanes 和碳酸钾处理 6-(羟甲基)呋喃并[2,3-d]嘧啶-2(3H)-酮 (2)，主要会生成 N3（和少量 O2）烷基化半异构体。用亚硫酰氯处理 3-烷基产物 (3) 会产生高活性的 6-氯甲基中间体 (5)。5 在醇溶液（约 50 °C）中直接溶解会产生 3-烷基-6-(烷氧基甲基)呋喃嘧啶-2(3H)-酮（6），而 5 在添加碱促进剂后会发生大量分解。用硫代乙酸钠在乙腈中对 5 进行超声处理，可得到在空气中稳定的 6-(烷基硫甲基)中间体 (7)，对这些中间体进行脱乙酰化（甲醇甲醇钠）和原位烷基化，可得到 3-烷基-6-(烷基硫甲基)呋喃并[2,3-d]嘧啶-2(3H)-酮 (8)。呋喃并[2,3-d]嘧啶-2(3H)-酮的亲脂性衍生物作为病毒穿透细胞的潜在抑制剂具有重要意义。

  DOI：

  10.1139/v06-042
• 作为产物：
  描述：

  5-(3-hydroxyprop-1yn-1-yl)pyrimidin-2,4-dione 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以60%的产率得到6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  An Efficient Alternative Route To 3,6-Disubstituted-Furo[2,3-d]Pyrimidin-2-One Analogues

  摘要：

  Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2, 3]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2, 3]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3- d ]pyrimidin-2-one analogues.

  DOI：

  10.1080/10810730500265757

文献信息

• Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines
  作者：Tatjana Gazivoda Kraljević、Andrea Bistrović、Matea Dedić、Sandra Kraljević Pavelić、Mirela Sedić、Silvana Raić-Malić

  DOI：10.1016/j.tetlet.2012.07.068

  日期：2012.9

  A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in good to excellent yields. The 5-endo-dig cyclisation of 5-alkynylpyrimidine derivatives promoted by a Pd-catalyst or base gives the corresponding furo[2,3-d]pyrimidines in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 6-(alkoxymethyl)- and 6-(alkylsulfanylmethyl)furo[2,3-<i>d</i>]pyrimidin-2(3<i>H</i>)-one analogues
  作者：Zlatko Janeba、Noha Maklad、Morris J Robins

  DOI：10.1139/v06-042

  日期：2006.4.1

  Treatment of 6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one (2) with 1-iodoalkanes and potassium carbonate resulted in predominant formation of N3 (and minor amounts of O2) alkylated regioisomers. Treatment of the 3-alkyl products (3) with thionyl chloride gave highly reactive 6-chloromethyl intermediates (5). Direct solvolysis of 5 in alcohol solutions (~50 °C) produced 3-alkyl-6-(alkoxymethyl)furopyrimidin-2(3H)-ones (6), whereas extensive decomposition of 5 occurred with added base promoters. Sonication of 5 with sodium thioacetate in acetonitrile gave the air-stable 6-(alkylsulfanylmethyl) intermediates (7), which were subjected to deacetylation (methanolic sodium methoxide) and in situ alkylation to give 3-alkyl-6-(alkylsulfanylmethyl)furo[2,3-d]pyrimidin-2(3H)-ones (8). Lipophilic derivatives of furo[2,3-d]pyrimidin-2(3H)-one are of interest as potential inhibitors of viral penetration of cells.Key words: furo[2,3-d]pyrimidin-2(3H)-ones, alkyl, ether and thioether derivatives of furo[2,3-d]pyrimidin-2(3H)-one.

  用 1-iodoalkanes 和碳酸钾处理 6-(羟甲基)呋喃并[2,3-d]嘧啶-2(3H)-酮 (2)，主要会生成 N3（和少量 O2）烷基化半异构体。用亚硫酰氯处理 3-烷基产物 (3) 会产生高活性的 6-氯甲基中间体 (5)。5 在醇溶液（约 50 °C）中直接溶解会产生 3-烷基-6-(烷氧基甲基)呋喃嘧啶-2(3H)-酮（6），而 5 在添加碱促进剂后会发生大量分解。用硫代乙酸钠在乙腈中对 5 进行超声处理，可得到在空气中稳定的 6-(烷基硫甲基)中间体 (7)，对这些中间体进行脱乙酰化（甲醇甲醇钠）和原位烷基化，可得到 3-烷基-6-(烷基硫甲基)呋喃并[2,3-d]嘧啶-2(3H)-酮 (8)。呋喃并[2,3-d]嘧啶-2(3H)-酮的亲脂性衍生物作为病毒穿透细胞的潜在抑制剂具有重要意义。
• An Efficient Alternative Route To 3,6-Disubstituted-Furo[2,3-<i>d</i>]Pyrimidin-2-One Analogues
  作者：Zlatko Janeba、Noha Maklad、Morris J. Robins

  DOI：10.1080/10810730500265757

  日期：2005.9.1

  Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2, 3]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2, 3]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3- d ]pyrimidin-2-one analogues.