9,9-dimethyl-9,10-dihydrophenanthrene | 27094-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,9-dimethyl-9,10-dihydrophenanthrene
• 英文别名: 10,10-dimethyl-9H-phenanthrene
• CAS: 27094-32-2
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: RYCFMDRSMPBMEB-UHFFFAOYSA-N

物化性质

• 沸点：
  316.5±12.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-(tert-butyl)phenyl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 9,9-dimethyl-9,10-dihydrophenanthrene
  参考文献：
  名称：

  Brönsted Acid-Mediated Intramolecular Cyclization of Biaryl Triazenes for the Synthesis of Fluorenes and 9,10-Dihydro-Phenanthrenes

  摘要：

  The efficient synthesis of fluorenes from biaryl triazenes is successfully developed Up to 27 examples of biaryl triazenes are converted into their corresponding fluorene derivatives in the presence of CF3COOH (4.0 equiv). Mechanism research indicates that the reaction undergoes concerted processes, and pentacoordinate carbocations may be involved in these reactions.

  DOI：

  10.1021/jo501640d

文献信息

• Solid-state construction of zigzag periphery <i>via</i> intramolecular C–H insertion induced by alumina-mediated C–F activation
  作者：Mikhail Feofanov、Andreas Förtsch、Konstantin Amsharov、Vladimir Akhmetov

  DOI：10.1039/d1cc05233k

  日期：——

  Here, we report a C(aryl)–C(sp³) coupling technique enabling construction of PAHs with zigzag periphery directly on non-metallic surfaces.

  在这里，我们报告了一种C(芳基)–C(sp³)偶联技术，可以直接在非金属表面上构建具有锯齿状边缘的多环芳烃。
• C(sp³)–H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes
  作者：Yichao Gu、Xueliang Sun、Bin Wan、Zhuoer Lu、Yanghui Zhang

  DOI：10.1039/d0cc04602g

  日期：——

  A palladium-catalyzed cross-coupling reaction of aryl halides with 2-chlorobenzoic acids has been developed. The reaction forms C(sp3), C(sp2)-palladacycles through C(sp3)–H activation. The palladacycles react with 2-chlorobenzoic acids through two successive C–C cross-couplings, and two C–C bonds are formed with high chemoselectivity. The reaction provides an innovative method for the synthesis of

  已经开发了芳基卤化物与2-氯苯甲酸的钯催化的交叉偶联反应。反应通过C（sp 3）–H活化形成C（sp 3），C（sp 2）-Palladacycles 。Palladacycles通过两个连续的C–C交叉偶联与2-氯苯甲酸反应，并以高化学选择性形成两个C–C键。该反应提供了一种合成9,10-二氢菲的创新方法。
• Reisse,A. et al., Bulletin de la Societe Chimique de France, 1970, p. 742 - 746
  作者：Reisse,A. et al.

  DOI：——

  日期：——
• Brönsted Acid-Mediated Intramolecular Cyclization of Biaryl Triazenes for the Synthesis of Fluorenes and 9,10-Dihydro-Phenanthrenes
  作者：Lijun Xu、Weijun Yang、Lili Zhang、Maozhong Miao、Zhigen Yang、Xin Xu、Hongjun Ren

  DOI：10.1021/jo501640d

  日期：2014.10.3

  The efficient synthesis of fluorenes from biaryl triazenes is successfully developed Up to 27 examples of biaryl triazenes are converted into their corresponding fluorene derivatives in the presence of CF3COOH (4.0 equiv). Mechanism research indicates that the reaction undergoes concerted processes, and pentacoordinate carbocations may be involved in these reactions.