225541
偶氮二甲酸二异丙酯
98%
别名:
DIAD, 偶氮二甲酸二异丙酯
质量水平
方案
98%
表单
liquid
杂质
≤2% dichloromethane
折射率
n20/D 1.420 (lit.)
沸点
75 °C/0.25 mmHg (lit.)
密度
1.027 g/mL at 25 °C (lit.)
官能团
azo
储存温度
2-8°C
SMILES字符串
CC(C)OC(=O)\N=N\C(=O)OC(C)C
InChI
1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
InChI key
VVWRJUBEIPHGQF-MDZDMXLPSA-N
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一般描述
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。
应用
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。
警示用语：
Warning
危险分类
Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
靶器官
Respiratory system
储存分类代码
10 - Combustible liquids
WGK
WGK 2
闪点(°F)
222.8 °F
闪点(°C)
106 °C
个人防护装备
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Aza-Baylis-Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile
Shi M and Zhao G-L
Tetrahedron, 60(9), 2083-2089 (2004)
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.
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)
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