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Merck
CN

793434

4-Tolyl-α-MIDA-boryl aldehyde

别名:

(6-Methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)(4-methylphenyl)acetaldehyde

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经验公式(希尔记法):
C14H16BNO5
化学文摘社编号:
分子量:
289.09
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
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InChI

1S/C14H16BNO5/c1-10-3-5-11(6-4-10)12(9-17)15-20-13(18)7-16(2)8-14(19)21-15/h3-6,9,12H,7-8H2,1-2H3

SMILES string

O=C1OB(C(C2=CC=C(C)C=C2)C([H])=O)OC(CN(C)C1)=O

InChI key

DCVSWHVQPHHNBM-UHFFFAOYSA-N

form

solid

mp

135-142 °C

functional group

aldehyde

storage temp.

2-8°C

General description

4-Tolyl-α-MIDA-boryl aldehyde is a-boryl aldehyde derivative. It can be synthesized from oxiranyl MIDA boronates, via rearrangement.

Application

This boronic acid derivative is in a series of the first known stable α-boryl aldehyde species. Through the employment of the MIDA-protected boronic ester, this building block has been shown as a precursor to the synthesis of unnatural amino acids.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

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Zhi He et al.
Journal of the American Chemical Society, 133(35), 13770-13773 (2011-08-04)
A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives

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The Yudin laboratory is known for the development of amphoteric molecules and their application in synthesis. The corresponding reagents possess nucleophilic and electrophilic functional groups that do not prematurely react with each other.

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