2-diphenylphosphoryl-N-methylbenzamide | 1246962-72-0

• 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-N-methylbenzamide
• CAS: 1246962-72-0
• 化学式: C₂₀H₁₈NO₂P
• 分子量: 335.342
• InChiKey: PBXRCCUKIFKGDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 碘甲烷 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.193 g的产率得到2-diphenylphosphoryl-N-methylbenzamide
  参考文献：
  名称：

  Synthesis, Structure, and Reactivity of N-Benzoyl Iminophosphoranes Ortho Lithiated at the Benzoyl Group

  摘要：

  Ortho lithiation of N-benzamido-P,P,P-triaryliminophosphoranes through deprotonation with alkyllithium bases was achieved with ortho-C=O and ortho-P=N chemoselectivity. However, the synthetic scope of these processes was rather limited. Ortho-lithiated N-benzamido-P,P,P-triphenyl-iminophosphorane 8 was efficiently prepared via lithium/halogen exchange of the corresponding ortho-brominated precursor with s-BuLi in THF at -90 degrees C. The reaction of 8 with a variety of electrophiles provides an easy and mild method for the regioselective synthesis of ortho-modified iminophosphoranes via C-C (alkylation and hydroxyalkylation) and C-X (X = I, Si, P, Sn, and Hg) bond-forming reactions. NMR characterization of 8 in THF solution showed that 8 exists as an equilibrium mixture of one monomer and two dimers. The Li atoms of these species become members of five-membered rings through chelation by the ortho-metalated carbon and the carbonyl oxygen. The dimers differ in the relative orientation of the two chelates with respect to the plane defined by the C,Li, core. The equilibrium between all species is established by splitting the dimers into monomers and subsequent recombination with formation of a different dimer.

  DOI：

  10.1021/jo101151s

文献信息

• [EN] SYNTHESIS OF LACTONE DERIVATIVES AND THEIR USE IN THE MODIFICATION OF PROTEINS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE LACTONE ET LEUR UTILISATION DANS LA MODIFICATION DE PROTÉINES
  申请人：GENIE BIOTECH UK LTD

  公开号：WO2021123229A1

  公开（公告）日：2021-06-24

  Site-specific modifications of proteins are desirable in biotechnological applications such as biopharmaceuticals, immunotherapy, vaccines, and are useful in chemical biology. Gluconoylation is a non-enzymatic, covalent, post-translational modification commonly observed on N-terminal His-Tags bearing proteins. We synthesized glucono-1,5-lactone derivatives, including azido variants for selective acylation. High yield acylation is achieved by simply mixing derivatives with target protein amidst diverse conditions of temperatures, aqueous buffers, excipients, or complex cell lysate.

  蛋白质的位点特异性修饰在生物技术应用中是可取的，例如生物制药、免疫疗法、疫苗，并且在化学生物学中也非常有用。葡萄糖酸化是一种非酶促的共价后翻译修饰，常见于带有N-末端His-标签的蛋白质上。我们合成了葡萄糖酸-1,5-内酯衍生物，包括用于选择性酰化的叠氮化衍生物。只需将衍生物与目标蛋白质混合在不同的温度、水溶液缓冲剂、辅料或复杂的细胞裂解液条件下，即可实现高产酰化。
• CHEMOSELECTIVE LIGATION
  申请人：SAXON Eliana

  公开号：US20070037964A1

  公开（公告）日：2007-02-15

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可以在生理条件下进行的化学选择性连接反应。一般来说，该发明涉及特定设计的膦化合物的缩合作用，该膦化合物可以提供两个反应物之间的酰胺键形成，从而产生一个包含膦基团的最终产物，或者可以被设计成包含可裂解的连接剂，使膦的取代基转移到叠氮化合物上，释放出一个氧化膦副产物，并在最终产物中产生一个天然的酰胺键。该反应的选择性及其与水性环境的兼容性使其可以应用于体内（例如在细胞表面或细胞内）和体外（例如合成肽和其他聚合物，生产改性（例如标记）氨基酸）。