9H-fluoren-9-one O-butyloxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-one O-butyloxime
• 英文别名: fluoren-9-one O-butyl-oxime；N-butoxyfluoren-9-imine
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: HTEONGBOYNKNDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-fluorenone O-tosyl-oxime 、 正丁醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到9H-fluoren-9-one O-butyloxime
  参考文献：
  名称：

  醇的分子间亲电O-胺化†

  摘要：

  我们报道了脂族醇的分子间亲电O-胺化的第一个例子。因此，新试剂甲苯磺酸芴酮肟5a或甲磺酸甲苯磺酸酯5b允许在温和条件下在NaH存在下对多种醇进行O胺化。通过跟踪生成的肟醚6，表明该反应对醇中的空间效应敏感。此外，发现在醇分子（苄基，烯丙基）中存在芳环或双键可提高反应速率。

  DOI：

  10.1021/jo061900m

文献信息

• An Efficient One-Pot Synthesis of Oxime Ethers from Alcohols Using Triphenylphosphine/Carbon Tetrachloride
  作者：Mohammad Soltani Rad、Ali Khalafi-Nezhad、Fatemeh Karimitabar、Somayeh Behrouz

  DOI：10.1055/s-0029-1218711

  日期：2010.5

  A convenient and efficient one-pot O-alkylation of oximes from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in

  描述了在三氯化碳中使用三苯基膦方便有效地从醇中进行肟的一锅O-烷基化。在这种方法中，在回流的乙腈中，在催化量的碘化四丁铵存在下，用三苯基膦，四氯化碳，肟和DBU的混合物处理醇，可以高收率提供相应的O-烷基醚。该方法是用各种结构多样的醇对肟进行高效的O-烷基化。对于不对称肟醚的半经验量子力学计算（AM1）表明Z异构体的形成热较低。 肟-醇-O-烷基化-三苯基膦-四氯化碳-DBU
• Electrochemical Reduction of Oximes in Aprotic Media.
  作者：Benoît Soucaze-Guillous、Henning Lund、Masato Hashimoto、Lage Pettersson、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0417

  日期：——

  The electrochemical reduction in N,N-dimethylformamide of (Z)- and (E)-benzaldoximes, derivatives thereof and some ketoximes has been investigated. The bases electrogenerated during the reduction of the benzaldoximes and their derivatives induce a catalytic elimination reaction producing benzonitrile. Two mechanisms are discussed, one in which the electrogenerated base eliminates water from the incoming substrate and one in which the base abstracts a proton from the intermediate benzaldimine radical with formation of benzonitrile radical anion; this radical anion then reduces the incoming substrate. The electrogenerated base formed during the reduction of the ketoximes deprotonates the oxime to the less reducible oxime anion. During the reduction of an acylated oxime: the parent oxime is formed, probably by cleavage induced by the electrogenerated base, but direct cleavage of the radical anion to the oxime might be possible.
• Intermolecular Electrophilic O-Amination of Alcohols
  作者：Alfred Hassner、Guy Patchornik、Tarun K. Pradhan、R. Kumareswaran

  DOI：10.1021/jo061900m

  日期：2007.1.1

  an intermolecular electrophilic O-amination of aliphatic alcohols. Thus, the new reagents, fluorenone oxime tosylate, 5a, or mesylate, 5b, permit O-amination of diverse alcohols in the presence of NaH under mild conditions. By following the formation of the resulting oxime ethers, 6, the reaction was shown to be sensitive to steric effects in the alcohol. Furthermore, the presence of an aromatic ring

  我们报道了脂族醇的分子间亲电O-胺化的第一个例子。因此，新试剂甲苯磺酸芴酮肟5a或甲磺酸甲苯磺酸酯5b允许在温和条件下在NaH存在下对多种醇进行O胺化。通过跟踪生成的肟醚6，表明该反应对醇中的空间效应敏感。此外，发现在醇分子（苄基，烯丙基）中存在芳环或双键可提高反应速率。