(4-(tert-butyl)phenyl)diphenylphosphine oxide | 1448632-01-6

• 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: (4-(tert-butyl)phenyl)diphenylphosphine oxide
• 英文别名: diphenyl(4-(tert-butyl)phenyl)phosphine oxide；1-Tert-butyl-4-diphenylphosphorylbenzene；1-tert-butyl-4-diphenylphosphorylbenzene
• CAS: 1448632-01-6
• 化学式: C₂₂H₂₃OP
• 分子量: 334.398
• InChiKey: OYUIFSJLNNDOFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  benzyldiphenylphosphine oxide 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium 作用下， 以 1,4-二氧六环 、 paraffin oil 为溶剂， 反应 48.0h， 生成 (4-(tert-butyl)phenyl)diphenylphosphine oxide
  参考文献：
  名称：

  Selective C–P(O) Bond Cleavage of Organophosphine Oxides by Sodium

  摘要：

  Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.

  DOI：

  10.1021/acs.joc.0c01642

文献信息

• Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds
  作者：Kaiqiang Xu、Long Liu、Zhaohui Li、Tianzeng Huang、Kang Xiang、Tieqiao Chen

  DOI：10.1021/acs.joc.0c01557

  日期：2020.11.20

  The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

  开发了可控制的硫酯磷酸化。当反应由钯催化剂催化时，当仅在碱的存在下进行反应时，芳基或烯基磷酰基化合物通过脱羰偶合产生，而苄基磷酰基化合物通过脱氧偶合产生。
• Palladium-Catalyzed C–P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide
  作者：Holly McErlain、Leanne M. Riley、Andrew Sutherland

  DOI：10.1021/acs.joc.1c02172

  日期：2021.12.3

  iodide-accelerated, palladium-catalyzed C–P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward

  描述了芳基九氟磺酸盐的碘化物加速、钯催化 C-P 键形成反应。该方案针对芳基氧化膦的合成进行了优化，并且被发现能够耐受多种芳基九氟磺酸盐。这种转化的一般性质是通过与其他 P(O)H 化合物偶联来合成芳基膦酸酯和芳基次膦酸酯而建立的。稳定、可分离的芳基九氟磺酸盐的直接合成，与快速的 C-P 键形成反应相结合，可以从容易获得的苯酚起始材料中轻松制备芳基磷目标化合物。通过有机发光二极管（OLED）材料和膦酰基苯丙氨酸模拟物的有效制备，证明了该总体策略的合成效用。
• Practical C–P bond formation via heterogeneous photoredox and nickel synergetic catalysis
  作者：Ernest Koranteng、Yi-Yin Liu、Si-Yue Liu、Qiang-Xian Wu、Liang-Qiu Lu、Wen-Jing Xiao

  DOI：10.1016/s1872-2067(19)63379-6

  日期：2019.12

  complexes as transition metal catalysts provided a variety of organophosphorus compounds from readily available aryl and vinyl halides, as well as aryl triflates, with generally a good-to-excellent reaction efficiency (31 examples, 46%-98% yields). The current protocol features mild reaction conditions, a broad substrate scope, recyclability of photocatalysts, and inexpensive catalysts, thus defining the practical

  摘要 利用多相光催化和镍催化相结合的协同催化策略，开发了一种高效的 C&-P 键形成反应。该平台利用硫化镉半导体作为非均相光催化剂和镍配合物作为过渡金属催化剂，从容易获得的芳基和乙烯基卤化物以及芳基三氟甲磺酸酯中提供各种有机磷化合物，通常具有良好的反应效率（31 个例子， 46%-98% 的产率）。目前的协议具有温和的反应条件、广泛的底物范围、光催化剂的可回收性和廉价的催化剂，从而定义了本催化剂系统的实用和经济特性。
• NiCl2 as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide
  作者：Shengmei Guo、Hu Cai、Wenjie Yan、Hongbo Zhou、Haoyuan Li、Huimin Hu、Ying Yu

  DOI：10.1055/a-1524-4912

  日期：2021.9

  Herein, NiCl2 was employed as a cheap precatalyst in the formation of C(sp2)-P bond via cross coupling reaction of phenol derivates and phosphine oxides/phosphites. This method allows a variety of phenols with diverse functional groups to transform to phosphates with good yields. No additional additive was used in this reaction.

  在此，NiCl2 被用作廉价的预催化剂，通过苯酚衍生物和氧化膦/亚磷酸酯的交叉偶联反应形成 C(sp2)-P 键。该方法允许具有不同官能团的多种酚以良好的产率转化为磷酸盐。在该反应中没有使用额外的添加剂。
• General Oxidative Aryl C–P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds
  作者：Jianyu Dong、Long Liu、Xuyu Ji、Qian Shang、Lixin Liu、Lebin Su、Bing Chen、Ruifeng Kan、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/acs.orglett.9b00922

  日期：2019.5.3

  Oxidative C–C/P–H cross-coupling is achieved via Pd-catalyzed decarbonylative cross-coupling of aroylhydrazides with P(O)H compounds. The unique cooperative reaction system, especially the Brønsted acid and bidentate phosphine ligand, allows the selective activation of the inert C–C bond and the suppression of the undesired oxidation and coordination of >P(O)–H compounds, leading to a general oxidative

  氧化的C / C / P-H交叉偶联是通过Pd催化的酰肼与P（O）H化合物的脱羰交叉偶联而实现的。独特的协同反应系统，特别是布朗斯台德酸和双齿膦配体，可以选择性活化惰性碳键，并抑制> P（O）–H化合物的不希望的氧化和配位，从而导致一般的氧化反应从容易获得的底物中合成芳基磷化合物。