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Bis(2-oxo-3-oxazolidinyl)phosphinic chloride 二(2-氧代-3-唑烷基)次膦酰氯

规格: 97%
CAS: 68641-49-6
产品编号: H78250
MDL: MFCD00010077
品牌: INFI

缩合剂系列产品

一个氨基酸的氨基与另一个氨基酸的羧基可以缩合成肽,形成的酰胺键在蛋白质化学中称为肽键。目前多肽合成中,主要采用羧基活化方法来完成缩合反应,最早使用的是将羧基活化为酰卤、酰基叠氮、活性酯、对称酸酐以及混合酸酐的方法,但是由于这些条件存在氨基酸消旋、反应试剂危险以及制备比较复杂等问题,后来逐渐被缩合试剂取代。添加缩合剂则无需活化羧基,实验操作简单方便且绿色环保。在众多缩合剂中,磷正离子缩合剂使得非天然氨基酸及有空间位阻的氨基酸顺利的完成多肽合成,卤代试剂例如PyBroP、BOP-Cl适合位阻大的氨基酸合成,避免发生外消旋作用(图一)。缩合剂除了可以合成酰胺以外,还应用于酯的合成,反应条件更加温和并且减少副反应干扰。

图一:Journal of Medicinal Chemistry, 2012, 55(23), 10610-10629

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Chemical NameBis(2-oxo-3-oxazolidinyl)phosphinic chloride
MDL NumberMFCD00010077
Synonym BOP-Cl Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Bis(2-oxo-3-oxazolidinyl)phosphorodiamidic Chloride 双(2-氧代-3-噁唑烷基)次磷酰氯 双(2-氧代-3-恶唑烷基)次磷酰氯
CAS Number68641-49-6
Beilstein Registry Number87564149
PubChem Substance ID87564149
EC Number250-023-7
Reaxys-RN3654596
Chemical Name Translation二(2-氧代-3-唑烷基)次膦酰氯
InChIKeyKLDLRDSRCMJKGM-UHFFFAOYSA-N
LabNetwork Molecule IDLN00009083
GHS Symbol
TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 170,23,1986

RTECSSZ5871000
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
    Packing GroupII
    UN Number 3261
    Risk Statements
    • R34 Causes burns 会导致灼伤
      Storage condition Moisture Sensitive 阴凉干燥处保存;易吸潮。
      WGK Germany3
      Precautionary statements
      • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
      • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
      • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
      • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
      • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
      • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
      • P301+P330+P331+P310
      • P303+P361+P353
      • P304+P340+P310
      • P305+P351+P338
      • P305+P351+P338+P310
      • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
      • P501 Dispose of contents/container to..… 处理内容物/容器.....
        Hazard statements
        • H290 May be corrosive to metals 可能腐蚀金属。
        • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
          Signal word Danger
          Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
          Hazard Codes 8 C
          Hazard Class8
        • 多肽缩合剂。适宜于因有空间位阻而不能与碳二亚胺类缩合剂反应的情形。
        • {ALF} For use in the direct selective 5'-acylation of nucleosides by carboxylic acids, (without 3'-protection), see: Tetrahedron, 44, 229 (1988). For high yield dehydration of carboxylic acids to anhydrides, see: Synthesis, 616 (1981). Also used in macrolide cyclization: J. Am. Chem. Soc., 104, 6818 (1982), and in formation of acyclic esters: Synth. Commun., 14, 515 (1984).
        • {ALF}
        • {ALF} Coupling reagent for which the rates of reaction with various nucleophiles are sufficiently different to permit a genuine "one-step" coupling of carboxylic acids with amines: Synthesis, 547 (1980). Particularly suitable for coupling N-alkyl amino acids: J. Org. Chem., 51, 3350 (1986). For discussion of strategies for one-step coupling in synthesis of amides, see: Synthesis, 413 (1984), and of the scope and limitations of the reagent in peptide coupling, see: Int. J. Pept. Prot. Res., 29, 574 (1987); J. Org. Chem., 55, 2895 (1990). See also Appendix 6.
        • {ALF} The mixed anhydride formed with carboxylic acids adds to imines to give ß-lactams: Synthesis, 63 (1982):
        • {ALF} These are also formed in high yield by cyclization of ß-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).
        • 68641-49-6 H78250 Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
二(2-氧代-3-唑烷基)次膦酰氯

          化学属性

          Mol. FormulaC6H8ClN2O5P
          Mol. Weight255
          Melting Point191
          TSCANo
          Density1.71
          Stability易吸潮

          *以上化合物性质及应用等信息仅供参考