5-fluorospiro[adamantane-2,2'-[1,3]dioxolane] | 1227734-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-fluorospiro[adamantane-2,2'-[1,3]dioxolane]
• 英文别名: 5-fluoro-2-adamantanone ethylene ketal；1'-Fluorospiro[1,3-dioxolane-2,4'-adamantane]；1'-fluorospiro[1,3-dioxolane-2,4'-adamantane]
• CAS: 1227734-59-9
• 化学式: C₁₂H₁₇FO₂
• 分子量: 212.264
• InChiKey: IYOIPYOBDDTBKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluorospiro[adamantane-2,2'-[1,3]dioxolane] 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以86%的产率得到5-氟-2-金刚烷酮
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t
• 作为产物：
  描述：

  5-hydroxy-2-adamantanone ethylene ketal 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到5-fluorospiro[adamantane-2,2'-[1,3]dioxolane]
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t

文献信息

• eFluorination Using Cheap and Readily Available Tetrafluoroborate Salts
  作者：Matthew C. Leech、Dmitrii Nagornîi、Jamie M. Walsh、Cyrille Kiaku、Darren L. Poole、Joseph Mason、Iain C. A. Goodall、Perry Devo、Kevin Lam

  DOI：10.1021/acs.orglett.2c04305

  日期：2023.3.10

  synthesis of tertiary hindered alkyl fluorides from carboxylic acids has been developed without the need for hydrofluoric acid salts or non-glass reactors. In this anodic fluorination, collidinium tetrafluoroborate acts as both the supporting electrolyte and fluoride donor. A wide range of functional groups has been shown to be compatible, and the possibility of scale-up using flow electrochemistry has also

  已经开发出一种实用的电化学方法，用于从羧酸快速、安全和温和地合成叔受阻烷基氟化物，而无需氢氟酸盐或非玻璃反应器。在这种阳极氟化反应中，四氟硼酸可力丁作为支持电解质和氟化物供体。广泛的官能团已被证明是相容的，并且还证明了使用流式电化学进行放大的可能性。