225541
偶氮二甲酸二异丙酯
98%
别名:
DIAD, 偶氮二甲酸二异丙酯
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关于此项目
线性分子式:
(CH3)2CHOOCN=NCOOCH(CH3)2
化学文摘社编号:
分子量:
202.21
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1912326
Assay:
98%
Form:
liquid
InChI
1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
SMILES string
CC(C)OC(=O)\N=N\C(=O)OC(C)C
InChI key
VVWRJUBEIPHGQF-MDZDMXLPSA-N
assay
98%
form
liquid
impurities
≤2% dichloromethane
Quality Level
bp
75 °C/0.25 mmHg (lit.)
density
1.027 g/mL at 25 °C (lit.)
functional group
azo
storage temp.
2-8°C
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General description
与二氧磷杂环己烷和铁催化剂反应，生成重排的鏻叶立德产物。
Application
作为反应物用于制备：
- 苯并哌喃，类似于传统的大麻素
- 丙型肝炎病毒NS5B聚合酶的MK-3281抑制剂
- 降冰片烯类富含胍聚合物,作为细胞穿透肽（CPP）的模拟物
- 铜绿假单胞菌群体感应分子N-(3-氧化十二烷酰基)-L-同型丝氨酸内酯的类似物,具有免疫抑制作用,但无LasR诱导特性
- 染料敏化太阳能电池的受体-供体-受体有机染料
- 1,3-二恶烷-2-羧酸衍生物，作为PPARα/γ双重激动剂
- 通过Morrison-Brunn-Huisgen甜菜碱的Mitsunobu和Arbuzov型多组分反应制备肼基膦酸盐和肼基二膦酸盐
偶氮二甲酸二异丙酯(DIAD)在有机合成中常用于制备有用的化学中间体。常用于光延(Mitsunobu)和氮杂Baylis-Hillman反应。DIAD也可用作N-苯甲基的选择性脱保护剂。
signalword
Warning
Hazard Classifications
Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
target_organs
Respiratory system
存储类别
10 - Combustible liquids
wgk
WGK 2
flash_point_f
222.8 °F
flash_point_c
106 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Zhi-Huang Qiu et al.
The Annals of thoracic surgery, 110(3), 925-932 (2020-01-29)
The efficacy of hemiarch replacement combined with a modified triple-branched stent graft in Debakey type I aortic dissection remains to be confirmed. From January 2016 to December 2017, 167 patients with acute Debakey type I aortic dissection underwent hemiarch replacement
Improved procedure for the selective N-debenzylation of benzylamines by diisopropyl azodicarboxylate
Kroutil J, et al.
Synthesis, 2004(03), 446-450 (2004)
An investigation of the Mitsunobu reaction in the preparation of peptide oxazolines, thiazolines, and aziridines
Wipf P and Miller CP
Tetrahedron Letters, 33(42), 6267-6270 (1992)
Marcelle L Ferguson et al.
Journal of the American Chemical Society, 128(14), 4576-4577 (2006-04-06)
Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields.
J Miles Blackburn et al.
Organic letters, 19(21), 6012-6015 (2017-10-20)
A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols.
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