1,3-difluorophenanthrene | 843614-82-4

• 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: 1,3-difluorophenanthrene
• 英文别名: Methyl (2E)-2-(5,7-ditert-butyl-1,3-benzoxathiol-2-ylidene)-3,3,3-trifluoropropanoate
• CAS: 843614-82-4
• 化学式: C₁₄H₈F₂
• 分子量: 214.214
• InChiKey: CWQMLMUMNMOJFB-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  337.7±15.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)
• 保留指数：
  1687;290.35

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-difluorophenanthrene 在 氢氧化钾 、 正丁基锂 、 二乙胺基三氟化硫 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-(1,3-difluorophenanthr-2-yl)-2-fluoropropionic acid
  参考文献：
  名称：

  Regioselectively Nucleus and/or Side-Chain Fluorinated 2-(Phenanthryl)propionic Acids by an Effective Combination of Radical and Organometallic Chemistry

  摘要：

  Regioselectively nucleus and/or side-chain fluorinated 2-(phenanthr-1-yl)- and 2-(phenanthr-2-yl)-propionic acids 1-5 were prepared using phenanthren-1(2H)-ones 6a-c as key intermediates. Thus. ethyl 2-(fluorophenanthryl)propionates 11 were obtained in good yields by Reformatsky reaction of 6a-c with ethyl 2-bromopropionate followed by dehydratation and DDQ-promoted aromatization of the resulting beta-hydroxyesters. Side-chain alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 14 were obtained by bromine/lithium permutation of dihydrophenanthryl bromides 12a-c with butyllithium followed by quenching of the lithiated intermediates with methyl pyruvate or ethyl 3,3,3-trifluoropyruvate and subsequent DDQ-promoted aromatization. The alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 25 were prepared by reacting 8-bromo-1,3-difluorophenanthrene 24 with butyllithium for 10 seconds at -110degreesC and subsequent addition of the suitable pyruvate to the lithiated intermediates. Alkyl 2-hydroxy-2-(phenanthr-2-yl)propionates 26 and 29 were suitably obtained by site-selective metalation of 1,3-difluorophenanthrene 28 and the bromophenanthrene 24: respectively, with LDA followed by quenching of the metalated intermediates with the Suitable alkyl pyruvate. Fluorination of the above alpha-hydroxypropionates with DAST, followed by the alkaline hydrolysis, allowed the expected 2-(phenanthryl)propionic acids 1-5 to be obtained in satisfactory overall yields.

  DOI：

  10.1021/jo048294k
• 作为产物：
  描述：

  6,8-difluoro-3,4-dihydrophenanthren-(2H)-1-one 在 正丁基锂 、 水 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(ll) bromide 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 1,3-difluorophenanthrene
  参考文献：
  名称：

  Regioselectively Nucleus and/or Side-Chain Fluorinated 2-(Phenanthryl)propionic Acids by an Effective Combination of Radical and Organometallic Chemistry

  摘要：

  Regioselectively nucleus and/or side-chain fluorinated 2-(phenanthr-1-yl)- and 2-(phenanthr-2-yl)-propionic acids 1-5 were prepared using phenanthren-1(2H)-ones 6a-c as key intermediates. Thus. ethyl 2-(fluorophenanthryl)propionates 11 were obtained in good yields by Reformatsky reaction of 6a-c with ethyl 2-bromopropionate followed by dehydratation and DDQ-promoted aromatization of the resulting beta-hydroxyesters. Side-chain alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 14 were obtained by bromine/lithium permutation of dihydrophenanthryl bromides 12a-c with butyllithium followed by quenching of the lithiated intermediates with methyl pyruvate or ethyl 3,3,3-trifluoropyruvate and subsequent DDQ-promoted aromatization. The alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 25 were prepared by reacting 8-bromo-1,3-difluorophenanthrene 24 with butyllithium for 10 seconds at -110degreesC and subsequent addition of the suitable pyruvate to the lithiated intermediates. Alkyl 2-hydroxy-2-(phenanthr-2-yl)propionates 26 and 29 were suitably obtained by site-selective metalation of 1,3-difluorophenanthrene 28 and the bromophenanthrene 24: respectively, with LDA followed by quenching of the metalated intermediates with the Suitable alkyl pyruvate. Fluorination of the above alpha-hydroxypropionates with DAST, followed by the alkaline hydrolysis, allowed the expected 2-(phenanthryl)propionic acids 1-5 to be obtained in satisfactory overall yields.

  DOI：

  10.1021/jo048294k

文献信息

• 一种作为OLED掺杂材料的含硼有机化合物及有机发光器件
  申请人：江苏三月科技股份有限公司

  公开号：CN114315876A

  公开（公告）日：2022-04-12

  本发明涉及一种作为OLED掺杂材料的含硼有机化合物及有机发光器件，属于半导体技术领域，本发明提供化合物的结构如通式(I)所示：本发明的化合物具有高荧光量子产率，具有高的玻璃化转变温度和分子热稳定性，以及具有合适的HOMO和LUMO能级，作为OLED发光器件的发光层材料中的掺杂材料使用时，器件寿命也得到了较大的改善，本发明含硼有机化合物作为发光层掺杂材料使器件具有良好的光电性能。
• 10.1021/acs.orglett.4c01484
  作者：Fu, Ying、Chen, Xi、Chen, Hao、Liu, Jia-Jia、Du, Zhengyin

  DOI：10.1021/acs.orglett.4c01484

  日期：——

  A ligand-free palladium-catalyzed and norbornadiene-mediated annulation reaction of iodoarenes with methyl 2-haloarenecarboxylates is reported. The sequentially accomplished reaction comprises intermolecular C–H arylation, followed by intramolecular decarboxylative annulation, affording various valuable phenanthrenes. This reaction protocol could be expanded to triphenylene syntheses whereby norbornene

  报道了碘芳烃与 2-卤代芳烃甲酸甲酯的无配体钯催化和降冰片二烯介导的环化反应。随后完成的反应包括分子间C-H芳基化，然后是分子内脱羧环化，得到各种有价值的菲。该反应方案可以扩展到苯并菲的合成，其中降冰片烯是助催化剂。有趣的是，甲酯的脱羧是通过溶剂介导的 C Me -O 键断裂完成的。
• Regioselectively Nucleus and/or Side-Chain Fluorinated 2-(Phenanthryl)propionic Acids by an Effective Combination of Radical and Organometallic Chemistry
  作者：Giacomo Ricci、Renzo Ruzziconi

  DOI：10.1021/jo048294k

  日期：2005.1.1

  Regioselectively nucleus and/or side-chain fluorinated 2-(phenanthr-1-yl)- and 2-(phenanthr-2-yl)-propionic acids 1-5 were prepared using phenanthren-1(2H)-ones 6a-c as key intermediates. Thus. ethyl 2-(fluorophenanthryl)propionates 11 were obtained in good yields by Reformatsky reaction of 6a-c with ethyl 2-bromopropionate followed by dehydratation and DDQ-promoted aromatization of the resulting beta-hydroxyesters. Side-chain alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 14 were obtained by bromine/lithium permutation of dihydrophenanthryl bromides 12a-c with butyllithium followed by quenching of the lithiated intermediates with methyl pyruvate or ethyl 3,3,3-trifluoropyruvate and subsequent DDQ-promoted aromatization. The alkyl 2-hydroxy-2-(phenanthr-1-yl)propionates 25 were prepared by reacting 8-bromo-1,3-difluorophenanthrene 24 with butyllithium for 10 seconds at -110degreesC and subsequent addition of the suitable pyruvate to the lithiated intermediates. Alkyl 2-hydroxy-2-(phenanthr-2-yl)propionates 26 and 29 were suitably obtained by site-selective metalation of 1,3-difluorophenanthrene 28 and the bromophenanthrene 24: respectively, with LDA followed by quenching of the metalated intermediates with the Suitable alkyl pyruvate. Fluorination of the above alpha-hydroxypropionates with DAST, followed by the alkaline hydrolysis, allowed the expected 2-(phenanthryl)propionic acids 1-5 to be obtained in satisfactory overall yields.