fluorenone 2',6'-dimethylanil | 75838-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: fluorenone 2',6'-dimethylanil
• 英文别名: N-(9H-fluoren-9-ylidene)-2,6-dimethylaniline；N-(2,6-dimethylphenyl)fluoren-9-imine
• CAS: 75838-45-8
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: DUFMIKXZUIQMBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  fluorenone 2',6'-dimethylanil 、 hexakis[2-(dimethylaminomethyl)phenyl]cyclotrisilane 以 甲苯 为溶剂， 反应 12.0h， 以77%的产率得到{2-[2-(2-Dimethylaminomethyl-phenyl)-1-(2,6-dimethyl-phenyl)-2,9b-dihydro-1H-1-aza-2-sila-cyclopenta[jk]fluoren-2-yl]-benzyl}-dimethyl-amine
  参考文献：
  名称：

  Reactions of a Silanediyl with Carbon−Oxygen and Carbon−Nitrogen Double Bonds

  摘要：

  Silanediyl 2 (generated by thermolysis of cyclotrisilane 1) reacts with benzophenone, tetracyclone, and fluorenone to yield products, which may originate from highly reactive siloxiranes as intermediates. However, using adamantanone as ketone, stable siloxirane 24 is obtained. The interaction of 2 with benzophenone anil or 36 gives heterocyclic compounds 31 and 37, respectively. The involvement of silaziridines in these reactions, as well as in the reactions of 1 with 1,4-diaza-1,3-butadienes 41a and b, which yield the expected formal [4 + 1] cycloaddition products, remains questionable.

  DOI：

  10.1021/jo951583b
• 作为产物：
  描述：

  2-溴联苯 、 2,6-二甲基苯基异腈 在 palladium diacetate 、 三苯基膦 、 cesium pivalate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以86%的产率得到fluorenone 2',6'-dimethylanil
  参考文献：
  名称：

  通过碳氢键的裂解，钯催化2-卤代芳基与异氰酸酯的环偶联

  摘要：

  为了证明异氰化物在催化CH键官能化反应中的实用性，开发了2-卤代双芳基与异氰化物的钯催化的环偶联反应。该反应通过在2-卤代联芳基的2'-位上的CH键断裂，提供了一系列芴酮亚胺衍生物。2，6-二取代的苯基异氰化物的使用对于进行该催化环偶联反应至关重要。该反应适用于杂环和乙烯基底物，从而允许构建广泛的环系统。观察到的大的动力学同位素效应（k H / k D = 5.3）表明，CH键的活化是该催化作用中的周转限制步骤。

  DOI：

  10.1021/jo1009728

文献信息

• Wakatsuki, Yasuo; Nomura, Okio; Tone, Hiroatsu, Journal of the Chemical Society. Perkin transactions II, 1980, p. 1344 - 1349
  作者：Wakatsuki, Yasuo、Nomura, Okio、Tone, Hiroatsu、Yamazaki, Hiroshi

  DOI：——

  日期：——
• WAKATSUKI YASUO; NOMURA OKIO; TONE HIROATSU; YAMAZAKI HIROSHI, J. CHEM. SOC. PERKIN TRANS., 1980, PART 2, NO 9, 1344-1349
  作者：WAKATSUKI YASUO、 NOMURA OKIO、 TONE HIROATSU、 YAMAZAKI HIROSHI

  DOI：——

  日期：——
• Palladium-Catalyzed Cyclocoupling of 2-Halobiaryls with Isocyanides via the Cleavage of Carbon−Hydrogen Bonds
  作者：Mamoru Tobisu、Shinya Imoto、Sana Ito、Naoto Chatani

  DOI：10.1021/jo1009728

  日期：2010.7.16

  2-halobiaryls with isocyanides was developed. The reaction afforded an array of fluorenone imine derivatives via the cleavage of a C−H bond at the 2′-position of 2-halobiaryls. The use of 2,6-disubstituted phenyl isocyanide was crucial for this catalytic cyclocoupling reaction to proceed. The reaction was applicable to heterocyclic and vinylic substrates, allowing the construction of a wide range of

  为了证明异氰化物在催化CH键官能化反应中的实用性，开发了2-卤代双芳基与异氰化物的钯催化的环偶联反应。该反应通过在2-卤代联芳基的2'-位上的CH键断裂，提供了一系列芴酮亚胺衍生物。2，6-二取代的苯基异氰化物的使用对于进行该催化环偶联反应至关重要。该反应适用于杂环和乙烯基底物，从而允许构建广泛的环系统。观察到的大的动力学同位素效应（k H / k D = 5.3）表明，CH键的活化是该催化作用中的周转限制步骤。
• Reactions of a Silanediyl with Carbon−Oxygen and Carbon−Nitrogen Double Bonds
  作者：Johannes Belzner、Heiko Ihmels、Lara Pauletto、Matthias Noltemeyer

  DOI：10.1021/jo951583b

  日期：1996.1.1

  Silanediyl 2 (generated by thermolysis of cyclotrisilane 1) reacts with benzophenone, tetracyclone, and fluorenone to yield products, which may originate from highly reactive siloxiranes as intermediates. However, using adamantanone as ketone, stable siloxirane 24 is obtained. The interaction of 2 with benzophenone anil or 36 gives heterocyclic compounds 31 and 37, respectively. The involvement of silaziridines in these reactions, as well as in the reactions of 1 with 1,4-diaza-1,3-butadienes 41a and b, which yield the expected formal [4 + 1] cycloaddition products, remains questionable.