2-(diphenylphosphoryl)benzamide | 1071983-26-0

• 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: 2-(diphenylphosphoryl)benzamide
• 英文别名: 2-(Diphenylphosphinyl) benzamide；2-diphenylphosphorylbenzamide
• CAS: 1071983-26-0
• 化学式: C₁₉H₁₆NO₂P
• 分子量: 321.315
• InChiKey: JQAANBMJTHKCIS-UHFFFAOYSA-N

物化性质

• 沸点：
  558.7±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 2-(diphenylphosphoryl)benzoate 在 sodium trioxodinitrate 、 三羟甲基氨基甲烷 作用下， 以 水 、 乙腈 为溶剂， 以60%的产率得到2-(diphenylphosphoryl)benzamide
  参考文献：
  名称：

  Reductive Phosphine-Mediated Ligation of Nitroxyl (HNO)

  摘要：

  Nitroxyl (HNO) demonstrates a unique chemical and biological profile compared to nitric oxide (NO). Phosphorus NMR studies reveal that HNO reacts with triarylphosphines to give the corresponding phosphine oxide and aza-ylide. In the presence of a properly situated electrophilic ester, the aza-ylide undergoes a Staudinger ligation to yield an amide with the nitrogen atom being derived from HNO. These results define new HNO reactivity and provide the basis of new HNO detection methods.

  DOI：

  10.1021/ol900914s

文献信息

• PREPARATION OF DIAZO AND DIAZONIUM COMPOUNDS
  申请人：Raines Ronald Thaddeus

  公开号：US20100125132A1

  公开（公告）日：2010-05-20

  A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.

  一种制备重氮化合物、其重氮盐和这些化合物的其他保护形式的方法。通过将携带反应性羰基基团的三级膦试剂与偶氮化物反应来制备重氮化合物。该反应还可以生成酰基三氮烯，可以通过热转化或加入碱来形成重氮化合物，或者可以分离出酰基三氮烯。该方法特别适用于将携带一个或多个电子吸引基团的偶氮化物转化为重氮化合物。该方法可以在温和条件下在水性介质中进行，并且特别适用于在生理条件下将偶氮糖转化为重氮化合物和其重氮盐。提供了三级膦试剂，特别是那些水溶性的试剂，以及用于制备这些试剂的前体。
• Disulfide formation via sulfenamides
  作者：Jia Pan、Ming Xian

  DOI：10.1039/c0cc02076a

  日期：——

  A phosphine-mediated one-step disulfide formation from S-nitrosothiols has been developed. This reaction can convert unstable S-nitrosothiols to stable disulfidesviasulfenamide intermediates under very mild conditions. It has the potential to be used for the detection ofS-nitrosothiols.

  我们开发了一种由磷化氢介导的一步法 S-亚硝硫醇二硫化物形成反应。该反应可在非常温和的条件下将不稳定的 S-亚硝硫醇转化为稳定的二硫化物-亚硫酰胺中间体。它具有用于检测 S-亚硝硫醇的潜力。
• Small Molecule Control of Morpholino Antisense Oligonucleotide Function through Staudinger Reduction
  作者：Kristie Darrah、Joshua Wesalo、Bradley Lukasak、Michael Tsang、James K. Chen、Alexander Deiters

  DOI：10.1021/jacs.1c08723

  日期：2021.11.10

  Conditionally activated, caged morpholino antisense agents (cMOs) are tools that enable the temporal and spatial investigation of gene expression, regulation, and function during embryonic development. Cyclic MOs are conformationally gated oligonucleotide analogs that do not block gene expression until they are linearized through the application of an external trigger, such as light or enzyme activity

  条件激活的笼状吗啉代反义试剂 (cMO) 是能够在胚胎发育过程中对基因表达、调控和功能进行时间​​和空间研究的工具。环状 MO 是构象门控寡核苷酸类似物，在通过应用外部触发因素（例如光或酶活性）使其线性化之前，它们不会阻断基因表达。在这里，我们描述了小分子响应性 cMO 的第一个例子，它们通过 Staudinger 还原进行快速有效的降解。这是通过高度灵活的链接器设计实现的，该链接器设计为安装化学激活的自焚基序提供了机会。我们针对两种不同的，合成了循环cMOs，发育相关基因，并证明了磷化氢触发的斑马鱼胚胎基因表达敲低。这是关于用于基因敲低的小分子触发反义试剂的第一份报告，为不断增长的基因敲低工具库增加了另一个生物正交条目。
• An isophorone-fused near-infrared fluorescent probe with a large Stokes shift for imaging endogenous nitroxyl in living cells and zebrafish
  作者：Chao Wei、Xiaofen Wang、Xueyan Li、Xu Jia、Xinya Hao、Jiangyan Zhang、Pingzhu Zhang、Xiaoliu Li

  DOI：10.1016/j.saa.2019.117765

  日期：2020.2

  excellent fluorescent probe for selective recognition and sensitive detection of HNO in biological systems. Near-infrared (NIR) fluorescent probes with a large Stokes shift are an ideal tool for bioimaging applications. Here, we have developed a NIR fluorescent probe with a large Stokes shift, namely, NIR-HNO, to monitor HNO in cells and zebrafish. NIR-HNO consists of an isophorone-fused NIR fluorescence

  硝基氧（HNO）在多种生理和病理过程中起着重要的作用，但是内源性HNO的详细产生机理仍然有待探索和完善。迫切需要开发一种出色的荧光探针，用于生物系统中HNO的选择性识别和灵敏检测。斯托克斯位移大的近红外（NIR）荧光探针是生物成像应用的理想工具。在这里，我们开发了一种具有大斯托克斯位移的NIR荧光探针，即NIR-HNO，以监视细胞和斑马鱼中的HNO。NIR-HNO由融合了异佛尔酮的NIR荧光报告分子和二苯基膦基苯甲酰基HNO响应单元组成。根据氮杂内酯分子内酯的氨解反应，NIR-HNO对HNO表现出快速的选择性NIR荧光开启响应，高灵敏度（检测极限为39.6 nM）和大斯托克斯位移（265 nm）。生物学成像结果表明，NIR-HNO是活体系统中内源性HNO成像的良好候选者。
• A FRET-based ratiometric two-photon fluorescent probe for dual-channel imaging of nitroxyl in living cells and tissues
  作者：Xiaoyan Zhu、Mengyi Xiong、Hong-wen Liu、Guo-jiang Mao、Liyi Zhou、Jing Zhang、Xiaoxiao Hu、Xiao-Bing Zhang、Weihong Tan

  DOI：10.1039/c5cc08695g

  日期：——

  A FRET-based ratiometric two-photon fluorescent probe for nitroxyl was first proposed and successfully applied in living cell and tissue imaging.

  一种基于FRET的比率双光子荧光探针用于亚硝酰的检测被首次提出并成功应用于活细胞和组织成像。