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Merck

166804

Sigma-Aldrich

偶氮二甲酸二苄酯

technical grade, 90%

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About This Item

线性分子式:
C6H5CH2OCON=NCOOCH2C6H5
CAS号:
分子量:
298.29
Beilstein:
2298734
EC號碼:
MDL號碼:
分類程式碼代碼:
12352100
PubChem物質ID:
NACRES:
NA.22

等級

technical grade

化驗

90%

形狀

solid

mp

43-47 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

O=C(OCc1ccccc1)\N=N\C(=O)OCc2ccccc2

InChI

1S/C16H14N2O4/c19-15(21-11-13-7-3-1-4-8-13)17-18-16(20)22-12-14-9-5-2-6-10-14/h1-10H,11-12H2/b18-17+

InChI 密鑰

IRJKSAIGIYODAN-ISLYRVAYSA-N

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一般說明

偶氮二甲酸二苄酯可以与糖发生[4+2]环加成反应,生成2-氨基糖苷

應用

偶氮二甲酸二苄酯被用作亲电试剂,用于通过脯氨酸催化的C-糖基烷基醛的α-胺化反应,合成C-糖基α-氨基酸。它被用于光学活性吡唑烷衍生物的对映选择性合成

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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Shengming Ma et al.
Organic letters, 6(13), 2193-2196 (2004-06-18)
[reaction: see text] Optically active pyrazolidine derivatives have been constructed by the Cu- and Pd-catalyzed asymmetric one-pot tandem addition-cyclization reaction of 2-(2',3'-dienyl)-beta-ketoesters, organic halides, and dibenzyl azodicarboxylate. The absolute configurations of the final products depend on the structure of the
[4+ 2] Cycloaddition reaction of dibenzyl azodicarboxylate and glycals.
Leblanc Y, et al.
Journal of the American Chemical Society, 111(8), 2995-3000 (1989)
Andrea Nuzzi et al.
Organic letters, 10(20), 4485-4488 (2008-09-16)
Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de >95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.

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