Merck
CN

699292

Sigma-Aldrich

反式-2-苯基乙烯基硼酸甲基亚氨基二乙酸酯

95%

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Empirical Formula (Hill Notation):
C13H14BNO4
分子量:
259.07
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

检测方案

95%

形式

powder

mp

185-195 °C

SMILES string

CN1CC(=O)OB(OC(=O)C1)\C=C\c2ccccc2

InChI

1S/C13H14BNO4/c1-15-9-12(16)18-14(19-13(17)10-15)8-7-11-5-3-2-4-6-11/h2-8H,9-10H2,1H3/b8-7+

InChI key

OFLDLTAQNBBGGU-BQYQJAHWSA-N

应用

trans-2-Phenylvinylboronic acid MIDA ester is a stable boronic acid surrogate, which can be used as a reactant in Suzuki-Miyaura cross-coupling reactions . It is also used as a precursor to prepare α-borylated phenyl ketone via the Wacker-type oxidation method.

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Synthesis of ?-borylated ketones by regioselective wacker oxidation of alkenylboronates
Corless VB, et al.
Organic Letters, 20(17), 5300-5303 (2018)
Nicholas A Isley et al.
Journal of the American Chemical Society, 135(47), 17707-17710 (2013-11-15)
New technology has been developed that enables Suzuki-Miyaura couplings involving widely utilized MIDA boronates to be run in water as the only medium, mainly at room temperature. The protocol is such that no organic solvent is involved at any stage;
Panchanan Maiti et al.
International journal of molecular sciences, 21(18) (2020-09-17)
Alzheimer's disease (AD) is characterized by amyloid (Aβ) aggregation, hyperphosphorylated tau, neuroinflammation, and severe memory deficits. Reports that certain boronic compounds can reduce amyloid accumulation and neuroinflammation prompted us to compare trans-2-phenyl-vinyl-boronic-acid-MIDA-ester (TPVA) and trans-beta-styryl-boronic-acid (TBSA) as treatments of deficits

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