11625
偶氮二甲酸二叔丁酯
purum, ≥98.0% (GC)
别名:
DBAD, NSC 109889, 二叔丁基偶氮二甲酸酯, 双（1，1-二甲基乙基）偶氮二羧酸
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关于此项目
线性分子式:
(CH3)3COCON=NCOOC(CH3)3
化学文摘社编号:
分子量:
230.26
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-796-9
Beilstein/REAXYS Number:
1911434
MDL number:
Assay:
≥98.0% (GC)
Form:
solid
General description
偶氮二甲酸二叔丁酯是Mitsunobu反应的酸不稳定试剂，可轻松分离产物以及烯醇酯和烷基锂的亲电胺化和肼化。
Application
反应物用于：
- 通过立体选择性硒环化/氧化脱硒化或肼化/环化反应制备六肽关键片段
- 不对称迈克尔加成反应
- 通过光延反应（Mitsunobu 反应）制备二肽基肽酶 IV 依赖性水溶性前药
- 通过立体选择性 N-酰基亚胺介导的环化和烯醇化胺化合成吡咯并喹啉模板，用于合成拟肽化合物
- 巴比尔型炔丙基化反应
- 合成细菌肽脱甲酰基酶（PDF）抑制剂 fumimycin
- 甘氨酸席夫碱的不对称胺化
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
C. Gennari et al.
Journal of the American Chemical Society, 108, 6394-6394 (1986)
D.A. Evans et al.
Journal of the American Chemical Society, 108, 6395-6395 (1986)
J.L. Vicario et al.
Tetrahedron Letters, 40, 7123 -7123 (1999)
Cong-Bin Ji et al.
Organic & biomolecular chemistry, 10(6), 1158-1161 (2012-01-11)
We report the first example of catalytic asymmetric direct amination of α-monosubstituted nitroacetates using di-tert-butyl azodicarboxylate. The simple and easily available Hatakeyama's catalyst β-ICD 11 was found to be a highly enantioselective catalyst for this reaction.
Masaru Kondo et al.
Angewandte Chemie (International ed. in English), 54(28), 8198-8202 (2015-05-28)
The catalytic enantioselective reaction of diphenylmethylidene-protected α-aminoacetonitriles with imines has been developed. Good yields and diastereo- and enantioselectivities were observed for the reaction of various imines using chiral bis(imidazoline)/Pd catalysts. The reaction of α-aminonitriles with di-tert-butyl azodicarboxylate afforded chiral α,α-diaminonitriles
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