diphenyl(9-fluorenyl)phosphine oxide | 42328-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: diphenyl(9-fluorenyl)phosphine oxide
• 英文别名: (9H-fluoren-9-yl)diphenylphosphine oxide；Fluorenyldiphenylphosphinoxid；Diphenylfluorenylphosphinoxid；9-Diphenylphosphinylfluorene；9-diphenylphosphoryl-9H-fluorene
• CAS: 42328-93-8
• 化学式: C₂₅H₁₉OP
• 分子量: 366.399
• InChiKey: LAVIHKKHGQDROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diphenyl(9-fluorenyl)phosphine oxide 在 草酰氯 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 15.5h， 以92%的产率得到diphenyl(9-fluorenyl)phosphine
  参考文献：
  名称：

  路易斯酸使酮磷酸化形成 C-P 键和 C-C 键：9-磷酰基芴衍生物的合成

  摘要：

  已报道了一种用于路易斯酸促进合成 9-磷酰基芴的有效方法。该方法侧重于酮膦酰化，通过磷醛醇消除在二苯甲酮和 H-次膦酸酯、H-亚磷酸酯和 H-氧化膦之间形成 C-P 键和 C-C 键，其中一系列 9-磷酰基以中等至极好的收率选择性地获得芴衍生物。

  DOI：

  10.1021/acs.orglett.1c02504
• 作为产物：
  描述：

  diphenyl(9-fluorenyl)phosphine 在 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以50%的产率得到diphenyl(9-fluorenyl)phosphine oxide
  参考文献：
  名称：

  New Halo Compounds of Si, P, As, AND Sb Bearing a Bulky Substituted Fluorenyl Group

  摘要：

  New halo compounds of Si, P, As, and Sb potential precursors of doubly-bonded derivatives of these elements, have been synthesized: dichloro-and difluorosilanes 2-6 bearing a methylfluorenyl group and a second substituent of various size (Me, Ph, Mes, R2CMe); dichlorophosphines 13 and 14, fluoro- and difluoroarsines 15 and 16 and fluorostibine 17, substituted by the diphenyl (or dimesityl) phosphinofluorenyl group. Phosphine oxide and sulfide 9 and 10 also have been prepared.

  DOI：

  10.1080/10426500390228639

文献信息

• Transition-Metal-Free and Base-Promoted Carbon–Heteroatom Bond Formation via C–N Cleavage of Benzyl Ammonium Salts
  作者：Long Liu、Yuanyuan Tang、Kunyu Wang、Tianzeng Huang、Tieqiao Chen

  DOI：10.1021/acs.joc.0c02992

  日期：2021.3.5

  carbon–heteroatom (C–P, C–O, C–S, and C–N) bonds via C–N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated

  据报道，在无过渡金属的条件下，通过苄基铵盐的C–N裂解，可以轻松而通用地构建碳-杂原子（C–P，C–O，C–S和C–N）键。的组合吨-BuOK和18-冠-6启用广泛取代的苄基铵盐的耦合容易地与不同类型的杂原子的亲核试剂，即，氢磷化合物，醇，硫醇和胺。证明了良好的功能组耐受性。还成功进行了放大反应和一锅合成。
• Electroluminescent Devices
  申请人：Kathirgamanathan Poopathy

  公开号：US20090167158A1

  公开（公告）日：2009-07-02

  In an OLED there is a reflectivity influencing layer ( 27 ) which is preferably semi-absorbent and in embodiments is dark coloured or black which is formed of a sublimable organometallic compound. The reflectivity influencing layer is formed between an electrode ( 29 or 22 ) and a light-emitting layer ( 25 ).
• Lewis Acid Enables Ketone Phosphorylation to Form a C–P Bond and a C–C Bond: Synthesis of 9-Phosphoryl Fluorene Derivatives
  作者：Xiao-Hong Wei、Chun-Yuan Bai、Ai-Jun Wang、Qiao-Liang Feng、Lian-Biao Zhao、Ping Zhang、Zhen-Hua Li、Qiong Su、Yan-Bin Wang

  DOI：10.1021/acs.orglett.1c02504

  日期：2021.9.17

  An efficient method for the Lewis acid promotion of the synthesis 9-phosphoryl fluorenes has been reported. This method focuses on ketone phosphonylation to form a C–P bond and a C–C bond between diphenylmethanone and H-phosphinate esters, H-phosphites, and H-phosphine oxides via phospha-aldol elimination, in which a series of 9-phosphoryl fluorene derivatives were selectively obtained in moderate

  已报道了一种用于路易斯酸促进合成 9-磷酰基芴的有效方法。该方法侧重于酮膦酰化，通过磷醛醇消除在二苯甲酮和 H-次膦酸酯、H-亚磷酸酯和 H-氧化膦之间形成 C-P 键和 C-C 键，其中一系列 9-磷酰基以中等至极好的收率选择性地获得芴衍生物。
• New Halo Compounds of Si, P, As, AND Sb Bearing a Bulky Substituted Fluorenyl Group
  作者：L. Baiget、M. Bouslikhane、J. Escudie、G. Cretiu Nemes、I. Silaghi-Dumitrescu、L. Silaghi-Dumitrescu

  DOI：10.1080/10426500390228639

  日期：2003.9.1

  New halo compounds of Si, P, As, and Sb potential precursors of doubly-bonded derivatives of these elements, have been synthesized: dichloro-and difluorosilanes 2-6 bearing a methylfluorenyl group and a second substituent of various size (Me, Ph, Mes, R2CMe); dichlorophosphines 13 and 14, fluoro- and difluoroarsines 15 and 16 and fluorostibine 17, substituted by the diphenyl (or dimesityl) phosphinofluorenyl group. Phosphine oxide and sulfide 9 and 10 also have been prepared.