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901233

Sigma-Aldrich

(2R)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole

≥95%

Sinônimo(s):

(R)-2-Phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine, (R)-Homobenzotetramisole, Birman (R)-HBTM

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About This Item

Fórmula empírica (Notação de Hill):
C16H14N2S
Número CAS:
1316861-19-4
Peso molecular:
266.36
Número MDL:
MFCD26793803
Código UNSPSC:
12161600
NACRES:
NA.22

Nível de qualidade

100

Ensaio

≥95%

Formulário

powder or chunks

pf

145-147 °C

grupo funcional

phenyl
thioether

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

C12=CC=CC=C1SC3=N[C@@H](C4=CC=CC=C4)CCN23

InChI

1S/C16H14N2S/c1-2-6-12(7-3-1)13-10-11-18-14-8-4-5-9-15(14)19-16(18)17-13/h1-9,13H,10-11H2/t13-/m1/s1

chave InChI

ZMYZJAQMQBHNLH-CYBMUJFWSA-N

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Aplicação

This chiral isothiourea homobenzotetramisole ((R)-HBTM) developed by the Birman lab is an organocatalyst that has been used for kinetic resolution, determination of absolute configuration, and nucleophile-catalysed, Michael–aldol-b-lactonization (NCMAL). This same product was previously listed as L511730, and the complementary (S)-HBTM organocatalyst (900542) is also available.

Outras notas


Technology Spotlight: Homobenzotetramisole (HBTM): A General Organocatalyst for Asymmetric Acylations

[1] Determination of the Absolute Configuration β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method

[2] Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl Transfer-Initiated Cascade

[3] Rapid assembly of complex cyclopentanes employing chiral, α, β-unsaturated acylammonium intermediates

[4] Determination of Absolute Configuration Using Kinetic Resolution Catalysts

[5] Kinetic Resolution of Secondary Alcohols Using Amidine-Based Catalysts

produto relacionado

Nº do produto
Descrição
Preços

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
MKCG0221

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Alexander J Wagner et al.
The Journal of organic chemistry, 81(15), 6253-6265 (2016-07-15)
Two different protocols were developed and optimized to address the need for (1) high sensitivity or (2) convenient utilization in the determination of the absolute configuration of secondary alcohols. The first protocol uses the competing enantioselective conversion (CEC) method to
Beatrice Ranieri et al.
The Journal of organic chemistry, 78(12), 6291-6296 (2013-05-22)
A concise approach to the synthesis of homobenzotetramisole and derivatives is described. Our strategy features a one-pot acylation-cyclization of 2-aminobenzothiazole with α,β-unsaturated acid chlorides to afford annulated pyrimidones. Subsequent Grignard addition followed by acid-promoted dehydration and reduction provides good overall
Nicholas A Ahlemeyer et al.
Organic letters, 18(14), 3454-3457 (2016-07-08)
A novel, reagent-free catalytic transformation of α,β-unsaturated thioesters into 2-substituted thiochromenes has been developed, with carbon dioxide as the only byproduct. Amidine-based catalysts, particularly homobenzotetramisole and its analogues, achieve high enantioselectivities and yields in this process.
Alexander J Wagner et al.
Organic letters, 13(16), 4470-4473 (2011-07-23)
A new method was developed to assign the absolute configuration of molecules using kinetic resolution catalysts. Secondary alcohols were acylated in the presence of Birman's S-HBTM and R-HBTM catalysts, and the fast-reacting catalyst was identified by NMR analysis of the
Matthew A Perry et al.
Organic letters, 15(3), 472-475 (2013-01-18)
A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An
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