benzo[d][1,3]dioxol-5-yldiphenylphosphane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzo[d][1,3]dioxol-5-yldiphenylphosphane
• 英文别名: 1,3-Benzodioxol-5-yl(diphenyl)phosphane
• 化学式: C₁₉H₁₅O₂P
• 分子量: 306.301
• InChiKey: ZZGBVIZFVUGNJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzo[d][1,3]dioxol-5-yldiphenylphosphane 在 双氧水 作用下， 以 水 为溶剂， 反应 0.17h， 以548 mg的产率得到benzo[d][1,3]dioxol-5-yldiphenylphosphine oxide
  参考文献：
  名称：

  高效氢氧化钾促进芳基卤与二苯基膦的 P-芳基化

  摘要：

  介绍了一种通过KOH促进的芳基卤与二苯基膦的P-芳基化反应合成三芳基膦化合物的简单方法。值得注意的是，这种转化可以在无过渡金属和温和的反应条件下以高产率顺利进行。此外，由于该协议操作方便且易于获得芳族卤化物，因此该协议对工业应用很有价值。基于实验数据提出了对反应机理的可能解释。

  DOI：

  10.1016/j.jorganchem.2021.121932
• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 、 二苯基膦 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.12h， 生成 benzo[d][1,3]dioxol-5-yldiphenylphosphane
  参考文献：
  名称：

  高效氢氧化钾促进芳基卤与二苯基膦的 P-芳基化

  摘要：

  介绍了一种通过KOH促进的芳基卤与二苯基膦的P-芳基化反应合成三芳基膦化合物的简单方法。值得注意的是，这种转化可以在无过渡金属和温和的反应条件下以高产率顺利进行。此外，由于该协议操作方便且易于获得芳族卤化物，因此该协议对工业应用很有价值。基于实验数据提出了对反应机理的可能解释。

  DOI：

  10.1016/j.jorganchem.2021.121932

文献信息

• Homogeneous and Heterogeneous Pd-Catalyzed Selective C–P Activation and Transfer Hydrogenation for “Group-Substitution” Synthesis of Trivalent Phosphines
  作者：Ming Lei、Xingyu Chen、Yingjie Wang、Liran Zhang、Hong Zhu、Zhiqian Wang

  DOI：10.1021/acs.orglett.2c00844

  日期：2022.4.22

  reported. The alkyl groups were introduced by alkylation of phosphines to form phosphonium salts. The “de-arylation” of phosphonium salts was achieved by C–P activation and transfer hydrogenation with homogeneous or heterogeneous Pd (0) catalysts. With this method, a series of trivalent phosphines were prepared from commercially available triarylphosphines. A chiral monophosphine ligand could be prepared

  报道了通过鏻盐的 C-P 活化合成三价膦的“基团取代”。通过膦的烷基化引入烷基以形成鏻盐。鏻盐的“去芳基化”是通过 C-P 活化和使用均相或非均相 Pd (0) 催化剂的转移氢化来实现的。采用这种方法，从市售的三芳基膦中制备了一系列三价膦。手性单膦配体可以从 BINAP 在“脱膦”过程中制备。
• Chiral diphosphine compound, intermediate for preparing the same, transition metal complex having the same diphosphine compound as ligand and asymmetric hydrogenation catalyst
  申请人：Takasago International Corporation

  公开号：EP0850945A1

  公开（公告）日：1998-07-01

  The present invention provides a novel diphosphine compound of the formula (I): where R1 and R2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, asymmetric hydrogenation catalyst.

  本发明提供了一种新型的式 (I) 二膦化合物： 其中 R1 和 R2 独立地代表环烷基、未取代或取代苯基或五元杂芳环。该化合物可用作不对称反应的配体，特别是不对称氢化催化剂。
• US5872273A
  申请人：——

  公开号：US5872273A

  公开（公告）日：1999-02-16
• Photoactivated Circularly Polarized Luminescent Organic Radicals in Doped Amorphous Polymer
  作者：Pengfei She、Yanyan Qin、Yuxiang Zhou、Xiaokang Zheng、Feiyang Li、Shujuan Liu、Yun Ma、Qiang Zhao、Wai‐Yeung Wong

  DOI：10.1002/anie.202403660

  日期：——

  Luminescent organic radicals, especially those with photoactivated circularly polarized luminescence (CPL) features, hold great significance for cutting‐edge optoelectronic applications, but their development still remains a challenge. In this study, we propose a novel strategy to achieve photoactivated CPL radicals by bonding two phosphine centers within an axial chiral system, yielding a compound of R/S‐5,5‐bis(diphenylphosphino)‐4,4′‐bibenzo[d][1,3]dioxole (R/S‐BDP). The photoactivated R/S‐BDP molecules in polymer matrix display a robust quantum yield of 19.8 % and a dissymmetry factor (g_lum) of 1.2×10⁻⁴, marking this work as the first example of photoactivated CPL radicals. Furthermore, the g_lum is improved to 1.0×10⁻² by using a liquid crystal as host. Experimental and theoretical analyses reveal that R/S‐BDP molecules, endowed with double phosphine cores in axial chirality, offer a direct way for intramolecular electron transfer upon photoirradiation. This leads to the generation of radical ionic pairs, which subsequently trigger the donor‐acceptor arrangement through intermolecular electron transfer, thereby resulting in stable radical emission. The extended photoactivated BDP‐F exhibits a remarkably high quantum efficiency of 57.8%. Ultimately, the distinctive photo‐responsive CPL radical luminescence has been successfully used for information displays and anti‐counterfeiting.
• Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine
  作者：Yang Zhou、Changchun Liu、Zhihao Shen、Bencai Dai、Jin Chen

  DOI：10.1016/j.jorganchem.2021.121932

  日期：2021.9

  by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism

  介绍了一种通过KOH促进的芳基卤与二苯基膦的P-芳基化反应合成三芳基膦化合物的简单方法。值得注意的是，这种转化可以在无过渡金属和温和的反应条件下以高产率顺利进行。此外，由于该协议操作方便且易于获得芳族卤化物，因此该协议对工业应用很有价值。基于实验数据提出了对反应机理的可能解释。