2-(二苯基膦酰基)乙胺 | 33921-17-4

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(二苯基膦酰基)乙胺
• 英文名称: (2-aminoethyl)diphenylphosphine oxide
• 英文别名: 2-Aminoaethyldiphenylphosphinoxid；2-(Diphenylphosphinyl)ethanamine；2-diphenylphosphorylethanamine
• CAS: 33921-17-4
• 化学式: C₁₄H₁₆NOP
• 分子量: 245.261
• InChiKey: PMLNXYWXKMFYII-UHFFFAOYSA-N

物化性质

• 沸点：
  367℃
• 密度：
  1.15
• 闪点：
  176℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(二苯基膦酰基)乙胺 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 2-(diphenylphosphinyl)ethanol
  参考文献：
  名称：

  Mastalerz,P.; Richtarski,G., Roczniki Chemii, 1971, vol. 45, p. 763 - 769

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基乙氧基膦 在 N₂N₄*H₂O 作用下， 生成 2-(二苯基膦酰基)乙胺
  参考文献：
  名称：

  Asymmetric Michael Addition Catalyzed by d-Glucose-based Azacrown Ethers

  摘要：

  我们合成了具有膦酰氧基烷基侧链（2 a - e）的新型糖基氮杂环醚。在 2-硝基丙烷与查尔酮（95% ee）和 3-呋喃-2-基-1-苯基-丙烯酮（80% ee）的迈克尔加成反应中，它们作为相转移催化剂显示出明显的不对称诱导作用。

  DOI：

  10.1055/s-2001-11395

文献信息

• A Tandem Dehydrogenation‐Driven Cross‐Coupling between Cyclohexanones and Primary Amines for Construction of Benzoxazoles
  作者：Biping Xu、Weiping Su

  DOI：10.1002/anie.202203365

  日期：2022.7.25

  A tandem dehydrogenation-driven cross-coupling reaction between cyclohexanones and primary amines is reported for benzoxazole synthesis by TEMPO's multiple reactivity modes (oxygenation and desaturation). This transition metal-free protocol features broad substrate scope, high functional group tolerance, and is operationally simple, therefore enabling late-stage functionalization and rapid synthesis

  据报道，通过 TEMPO 的多种反应模式（氧化和去饱和）合成苯并恶唑，环己酮和伯胺之间的串联脱氢驱动的交叉偶联反应。这种无过渡金属方案具有广泛的底物范围、高官能团耐受性和操作简单，因此能够实现生物活性化合物的后期功能化和快速合成，包括结构复杂的上市药物和天然产物。
• Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer
  作者：Nobuaki Soh、Osamu Sakawaki、Koji Makihara、Yuka Odo、Tuyoshi Fukaminato、Tsuyoshi Kawai、Masahiro Irie、Toshihiko Imato

  DOI：10.1016/j.bmc.2004.11.023

  日期：2005.2

  A novel fluorescent probe, 7-hydroxy-2-oxo-N-(2-(diphenylphosphino)ethyl)-2H-chromene-3-carboxamide (DPPEA-HC) was developed for use in monitoring hydrogen peroxide (H2O2) production. DPPEA-HC, which consists of a diphenylphosphine moiety and a 7-hydroxycoumarin moiety, reacts with H2O2 to form DPPEA-HC oxide, which is analogous to the reaction of triphenylphosphine with hydroperoxides such as H2O2 to form triphenylphosphine oxide. Photoinduced electron transfer (PET) was applied in the design of DPPEA-HC. Since the diphenylphosphine moiety and the 7-hydroxycoumarin moiety would act as the PET donor and the acceptor, respectively, it would be expected that DPPEA-HC would rationally cancel the PET process via the formation of DPPEA-HC oxide, based on the calculated energy levels of the donor and the acceptor moieties using the B3LYP/6-31G*//AM1 method. The fluorescence intensity of DPPEA-HC increased on the addition of a H2O2 solution in 100 mM sodium phosphate buffer (pH7.4), as predicted from the energy level calculation and a good correlation between increase in the fluorescence of DPPEA-HC and the concentration of H2O2 was observed. DPPEA-HC was also fluoresced by H2O2, which was enzymatically produced in xanthine/xanthine oxidase/superoxide dismutase (XA/XOD/SOD) system. The increase in the fluorescence of DPPEA-HC in the presence of H2O2 immediately ceased on the addition of catalase (CAT), which catalyzes the disproportionation of H2O2. In addition, DPPEA-HC was found to have a much higher selectivity for H2O2 and a greater resistance to autoxidation than 2',7'-dichlorodihydrofluoresein (DCFH). Time-resolved fluorescence measurements of DPPEA-HC and DPPEA-HC oxide confirmed that the fluorescence off/on switching mechanism of DPPEA-HC is based on the PET on/off control. (C) 2004 Elsevier Ltd. All rights reserved.
• Mastalerz,P.; Richtarski,G., Roczniki Chemii, 1971, vol. 45, p. 763 - 769
  作者：Mastalerz,P.、Richtarski,G.

  DOI：——

  日期：——
• Asymmetric Michael Addition Catalyzed by d-Glucose-based Azacrown Ethers
  作者：Tibor Novák、János Tatai、Péter Bakó、Mátyás Czugler、György Keglevich、László Tóke

  DOI：10.1055/s-2001-11395

  日期：——

  Novel sugar-based azacrown ethers with phosphinoxidoalkyl side chain (2 a - e) have been synthesized. They show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee) and to 3-fur-2-yl-1-phenyl-propenone (80% ee).

  我们合成了具有膦酰氧基烷基侧链（2 a - e）的新型糖基氮杂环醚。在 2-硝基丙烷与查尔酮（95% ee）和 3-呋喃-2-基-1-苯基-丙烯酮（80% ee）的迈克尔加成反应中，它们作为相转移催化剂显示出明显的不对称诱导作用。