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HATU - 版本历史
2026-07-16T19:18:20Z
在这个wiki上该页的修订历史
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<p><b>新页面</b></p><div>{{Chembox<br />
| ImageFile = HATU PF6 - iminium isomer.png<br />
| ImageSize = 180px<br />
| ImageFile2 = O-HATU_Structural_Formula_V1.svg<br />
| ImageSize2 = 200px<br />
| IUPACName = O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate<br />
| OtherNames = <br />
| Section1 = {{Chembox Identifiers<br />
| CASNo = 148893-10-1<br />
| CASNo_Ref = {{cascite|correct|CAS}}<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = B93RIH1T7E<br />
| PubChem = 9886157<br />
| ChemSpiderID = 8061830<br />
| SMILES = CN(C)C(=[N+](C)C)On1c2c(cccn2)nn1.F[P-](F)(F)(F)(F)F<br />
| InChI = 1/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1<br />
| InChIKey = JNWBBCNCSMBKNE-UHFFFAOYAG<br />
| StdInChI = 1S/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1<br />
| StdInChIKey = JNWBBCNCSMBKNE-UHFFFAOYSA-N<br />
}}<br />
| Section2 = {{Chembox Properties<br />
| C = 10 | H = 15 | F = 6 | N = 6 | O = 1 | P = 1<br />
| Appearance = 白色晶体粉末}}<br />
}}<br />
<br />
'''HATU'''（缩写自'''H'''exafluorophosphate '''A'''zabenzotriazole '''T'''etramethyl '''U'''ronium，六氟磷酸氮杂苯并三唑四甲基脲<ref>注释：HATU可以以脲盐（''O''-异构体）或活性较弱的亚铵盐（''N''-异构体）形式存在。</ref>）是一种[[多肽合成|多肽偶联]]的试剂，可将[[羧酸]]转化为{{le|活性酯|active ester}}。它通常在[[二甲基甲酰胺]]或其它极性非质子溶剂中与[[N,N-二异丙基乙基胺|二异丙基乙胺]]、[[三乙胺]]一起使用以构筑[[酰胺]]键。<ref>{{cite web | url=http://commonorganicchemistry.com/Rxn_Pages/Amine_to_Amide_Coupling/Amine_to_Amide_Coupling_HATU.htm | title=Amine to Amide (Coupling) - HATU | accessdate=2026-01-17 | archive-date=2024-09-08 | archive-url=https://web.archive.org/web/20240908162159/http://commonorganicchemistry.com/Rxn_Pages/Amine_to_Amide_Coupling/Amine_to_Amide_Coupling_HATU.htm | dead-url=no }}</ref><br />
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HATU的反应机理如下：<ref>{{cite journal | doi = 10.1021/ol006013z | pmid = 10930256 | title = Comparison of the Effects of 5- and 6-HOat on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers†,‡ | journal = Organic Letters | volume = 2 | issue = 15 | pages = 2253–2256 | year = 2000 | last1 = Carpino | first1 = Louis A | last2 = Imazumi | first2 = Hideko | last3 = Foxman | first3 = Bruce M | last4 = Vela | first4 = Michael J | last5 = Henklein | first5 = Peter | last6 = El-Faham | first6 = Ayman | last7 = Klose | first7 = Jana | last8 = Bienert | first8 = Michael }}</ref><br />
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: [[File:Mechanism of N-acylation using HATU.png|500px|Mechanism of N-acylation using HATU]]<br />
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==安全==<br />
HATU有潜在的致敏性。<ref>{{Cite journal |last1=McKnelly |first1=Kate J. |last2=Sokol |first2=William |last3=Nowick |first3=James S. |date=2020-02-07 |title=Anaphylaxis Induced by Peptide Coupling Agents: Lessons Learned from Repeated Exposure to HATU, HBTU, and HCTU |url=https://pubs.acs.org/doi/10.1021/acs.joc.9b03280 |journal=The Journal of Organic Chemistry |language=en |volume=85 |issue=3 |pages=1764–1768 |doi=10.1021/acs.joc.9b03280 |pmid=31849224 |issn=0022-3263 |url-access=subscription |access-date=2026-01-16 |archive-date=2025-08-02 |archive-url=https://web.archive.org/web/20250802002804/https://pubs.acs.org/doi/10.1021/acs.joc.9b03280 |dead-url=no }}</ref>[[差示扫描量热法|差示扫描量热测试]]（DSC）表明，它具有爆炸风险。<ref>{{Cite journal |last1=Sperry |first1=Jeffrey B. |last2=Minteer |first2=Christopher J. |last3=Tao |first3=JingYa |last4=Johnson |first4=Rebecca |last5=Duzguner |first5=Remzi |last6=Hawksworth |first6=Michael |last7=Oke |first7=Samantha |last8=Richardson |first8=Paul F. |last9=Barnhart |first9=Richard |last10=Bill |first10=David R. |last11=Giusto |first11=Robert A. |last12=Weaver |first12=John D. |date=2018-09-21 |title=Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing |url=https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193 |journal=Organic Process Research & Development |language=en |volume=22 |issue=9 |pages=1262–1275 |doi=10.1021/acs.oprd.8b00193 |issn=1083-6160 |url-access=subscription |access-date=2026-01-16 |archive-date=2024-12-04 |archive-url=https://web.archive.org/web/20241204023403/https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193 |dead-url=no }}</ref><br />
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==参考文献==<br />
{{reflist}}<br />
<br />
[[Category:肽偶联试剂]]<br />
[[Category:六氟磷酸盐]]<br />
[[Category:胍盐]]</div>
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