2-fluoro-9-fluorenone hydrazone | 342-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-fluoro-9-fluorenone hydrazone
• 英文别名: 2-Fluor-fluorenon-(9)-hydrazon；2-Fluor-9-hydrazonofluoren；(2-fluorofluoren-9-ylidene)hydrazine
• CAS: 342-99-4
• 化学式: C₁₃H₉FN₂
• 分子量: 212.226
• InChiKey: IDJKQDALUZJWCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-fluoro-9-fluorenone hydrazone 在 manganese dioxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以to provide 6.5 g (100%) of product (13) as a red solid which的产率得到2-fluoro-9-diazofluorene
  参考文献：
  名称：

  Spirofluoreneisothiazolidinone dioxides as aldose reductase inhibitors

  摘要：

  本发明揭示了新的螺噻唑啉二氧化物类芴异构体及其制备方法。

  公开号：

  US04968809A1
• 作为产物：
  描述：

  2-氟-9-芴酮 在 一水合肼 作用下， 反应 24.0h， 生成 2-fluoro-9-fluorenone hydrazone
  参考文献：
  名称：

  Synthesis of substituted fluorenones and substituted 3',3'-dichlorospiro[fluorene-9,2'-thiiranes] and their reactivities

  摘要：

  Several novel 9-fluorenones were synthesized and were used as precursors in an attempt to prepare unique substituted 3',3'-dichlorospiro[fluorene-9,2'-thiiranes]. Several of the thiiranes were unstable and desulfurized during their preparation (7a-d,11,12). 3',3'-Dichloro(2,5-dimethoxyspiro[fluorene-9,2'-thiirane] (7f) was prepared along with 2,2-dichloro-3,3-bis(4-methoxyphenyl)thiirane (16), and 3',3'-dichloro-10,11-dihydrospiro[5H-dibenzo[a,d]cycloheptane-5,2'-thiirane] (17) all of which were stable at room temperature. A study of the reactivity of fluorenyl-substituted thiiranes and other related thiiranes showed that the extent of aromaticity of the substituents at the 3-position of the thiiranes influences their stabilities.

  DOI：

  10.1021/jo00068a039

文献信息

• Spiro[fluoreneisothiazolidin]one dioxides: new aldose reductase and L-hexonate dehydrogenase inhibitors
  作者：Mark T. DuPriest、Brenda W. Griffin、Daniel Kuzmich、Loretta G. McNatt

  DOI：10.1021/jm00115a011

  日期：1991.11

  The first examples of spiro[fluorene-9,4'- and -9,5'-isothiazolidin]one dioxides (1 and 2) were synthesized and screened for activity as aldose reductase and L-hexonate dehydrogenase inhibitors. Compared to compounds 1, and 9,5'-compounds 2, synthesized from fluorene-9-sulfonamides by alkylation at C(9) with ethyl bromoacetate followed by cyclization, were more active, but relatively nonselective, inhibitors of aldose reductase and L-hexonate dehydrogenase, with IC50 values for in vitro inhibition of both enzymes on the order of 10(-7)-10(-8) M. However, the isomeric 9,4'-compounds 1, prepared by alkylation of fluorene-9-carboxylic acid esters with bromo- or iodo-methanesulfonamide followed by cyclization, were more selective inhibitors Of L-hexonate dehydrogenase with IC50 values of about 10(-6) M.