5-methoxy-3-tetrahydrofuran-3-methanol | 143724-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 5-methoxy-3-tetrahydrofuran-3-methanol
• 英文别名: (rel)-(1S/1R,3S)-(tetrahydro-1-methoxyfuran-3-yl)methanol；(5-Methoxyoxolan-3-yl)methanol
• CAS: 143724-42-9
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: LGKOEGIDJMJFBW-UHFFFAOYSA-N

物化性质

• 沸点：
  206.3±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-tetrahydrofuran-3-methanol 在 吡啶 、 Dowex HCR-S-H⁺ 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 4-<<(phenoxycarbonyl)oxy>methyl>-2-(octadecyloxy)tetrahydrofuran
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007
• 作为产物：
  描述：

  4-hydroxymethyl-5H-furan-2-one 在 盐酸 、 三氟甲磺酸 、 5%-palladium/activated carbon 、 氨 、 氢气 、 lithium 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 5-methoxy-3-tetrahydrofuran-3-methanol
  参考文献：
  名称：

  新型5'-脱氧-5'，5'-二氟苏糖基核苷膦酸类似物的合成及抗逆转录病毒活性

  摘要：

  新型5'-脱氧-5'，5'-二氟苏糖嘌呤膦酸类似物是从2-丙酮-1,3-二乙酸酯设计和合成的。用（二硫代二氟甲基）膦酸二乙酯直接置换三氟甲磺酸酯中间体12提供了相应的（α，α-二氟烷基）膦酸酯13。在Vorbrüggen条件下成功地从糖基供体14进行缩合，以分别提供核苷膦酸酯类似物15α，15β，18α和18β。氨解和膦酸酯的水解15β和18β，得到核苷膦酸类似物16，17，19b和20。另外，进行腺嘌呤衍生物的前药的合成以增加细胞摄取。对合成的核苷类似物进行了针对人类免疫缺陷病毒（HIV）-1的抗病毒筛选。腺嘌呤类似物的Bis（SATE）前药22对HIV-1具有明显的体外活性。

  DOI：

  10.1002/bkcs.10390

文献信息

• Synthesis of ()-2′-oxa-carbocyclic-2′,3′-dideoxynucleosides as potential anti-HIV agents
  作者：Mark J. Bamford、David C. Humber、Richard Storer

  DOI：10.1016/0040-4039(91)80873-5

  日期：1991.1

  Novel 2′,3′-dideoxynucleosides, having the pentofuranosyl oxygen at the 2′-position, were obtained by a short synthetic route from diethyl malonate and bromoacetaldehyde dimethyl acetal. The results of biological testing against HIV-1 in vitro are presented.

  通过丙二酸二乙酯和溴乙醛二甲基乙缩醛的短合成路线获得了在2'-位具有戊呋喃糖基氧的新型2'，3'-二脱氧核苷。介绍了针对HIV-1的体外生物测试结果。
• Kinoshita, Takamasa; Hirano, Madoka, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 1025 - 1026
  作者：Kinoshita, Takamasa、Hirano, Madoka

  DOI：——

  日期：——
• Synthesis and Anti-Retroviral Activity of Novel 5′-Deoxy-5′,5′-difluoro-threosyl Nucleoside Phosphonic Acid Analogs
  作者：Seyeon Kim、Jun-Pil Jee、Joon Hee Hong

  DOI：10.1002/bkcs.10390

  日期：2015.8

  Novel 5′‐deoxy‐5′,5′‐difluoro‐threose purine phosphonic acid analogs were designed and synthesized from 2‐propanone‐1,3‐diacetate. Direct displacement of the triflate intermediate 12 with diethyl (lithiodifluoromethyl)phosphonate provided the corresponding (α,α‐difluoroalkyl) phosphonate 13. Condensation successfully proceeded from a glycosyl donor 14 under Vorbrüggen conditions to provide the nucleoside

  新型5'-脱氧-5'，5'-二氟苏糖嘌呤膦酸类似物是从2-丙酮-1,3-二乙酸酯设计和合成的。用（二硫代二氟甲基）膦酸二乙酯直接置换三氟甲磺酸酯中间体12提供了相应的（α，α-二氟烷基）膦酸酯13。在Vorbrüggen条件下成功地从糖基供体14进行缩合，以分别提供核苷膦酸酯类似物15α，15β，18α和18β。氨解和膦酸酯的水解15β和18β，得到核苷膦酸类似物16，17，19b和20。另外，进行腺嘌呤衍生物的前药的合成以增加细胞摄取。对合成的核苷类似物进行了针对人类免疫缺陷病毒（HIV）-1的抗病毒筛选。腺嘌呤类似物的Bis（SATE）前药22对HIV-1具有明显的体外活性。
• 4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists
  作者：Elena Carceller、Manuel Merlos、Marta Giral、Javier Bartroli、Julian Garcia-Rafanell、Javier Forn

  DOI：10.1021/jm00082a007

  日期：1992.2

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.