2,4-difluoro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzene | 315204-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-difluoro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzene
• 英文别名: 2-[(2,4-Difluorophenyl)methoxy]propane-1,3-diol
• CAS: 315204-43-4
• 化学式: C₁₀H₁₂F₂O₃
• 分子量: 218.2
• InChiKey: QXNLYZYZQMTCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-difluoro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzene 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 反应 12.0h， 以83%的产率得到5-iodo-2,4-difluoro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzene
  参考文献：
  名称：

  Syntheses of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-Propoxy)methyl]- Derivatives of 5-Substituted-2,4-difluorobenzene: Unnatural Acyclo Thymidine Mimics for Evaluation as Anticancer and Antiviral Agents

  摘要：

  A group of 1 -[(2-hydroxyethoxy)methyl] - (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO(2)) were designed with the expectation that they may serve as acyclic 5-substituted-2'-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R= Me, H, I) were inactive as anticancer agents (CC(50) = 10(-3) to 10(-4) M range), whereas the 5-nitro compounds (12d, 13d) exhibided weak-to-moderate cytotoxicity (ICC(50) = 10(-5) to 10(-6) M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus(HSV-1 and HSV-2).

  DOI：

  10.1080/15257770008033850
• 作为产物：
  描述：

  2,4-二氟溴苄 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 2,4-difluoro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzene
  参考文献：
  名称：

  Syntheses of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-Propoxy)methyl]- Derivatives of 5-Substituted-2,4-difluorobenzene: Unnatural Acyclo Thymidine Mimics for Evaluation as Anticancer and Antiviral Agents

  摘要：

  A group of 1 -[(2-hydroxyethoxy)methyl] - (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO(2)) were designed with the expectation that they may serve as acyclic 5-substituted-2'-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R= Me, H, I) were inactive as anticancer agents (CC(50) = 10(-3) to 10(-4) M range), whereas the 5-nitro compounds (12d, 13d) exhibided weak-to-moderate cytotoxicity (ICC(50) = 10(-5) to 10(-6) M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus(HSV-1 and HSV-2).

  DOI：

  10.1080/15257770008033850

文献信息

• Syntheses of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-Propoxy)methyl]- Derivatives of 5-Substituted-2,4-difluorobenzene: Unnatural Acyclo Thymidine Mimics for Evaluation as Anticancer and Antiviral Agents
  作者：Zhi-Xian Wang、Weili Duan、Leonard I. Wiebe、Erik De Clercq、Jan Balzarini、Edward E. Knaus

  DOI：10.1080/15257770008033850

  日期：2000.9

  A group of 1 -[(2-hydroxyethoxy)methyl] - (12) and 1-[(1,3-dihydroxy-2-propoxy)methyl]- (13) derivatives of 2,4-difluorobenzene possessing a variety of C-5 substituents (R = Me, H, I, NO(2)) were designed with the expectation that they may serve as acyclic 5-substituted-2'-deoxyuridine (thymidine) mimics. Compounds 12 and 13 (R= Me, H, I) were inactive as anticancer agents (CC(50) = 10(-3) to 10(-4) M range), whereas the 5-nitro compounds (12d, 13d) exhibided weak-to-moderate cytotoxicity (ICC(50) = 10(-5) to 10(-6) M range) against a variety of cancer cell lines. All compounds prepared (12a-d, 13a-d) were inactive as antiviral agents in a broad-spectrum antiviral screen that also included the human immunodeficiency virus (HIV-1 and HIV-2) and herpes simplex virus(HSV-1 and HSV-2).