901233
(2R)-2-Phenyl-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazole
≥95%
Synonym(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
Empirical Formula (Hill Notation):
C16H14N2S
CAS Number:
Molecular Weight:
266.36
UNSPSC Code:
12161600
NACRES:
NA.22
MDL number:
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
SMILES string
C12=CC=CC=C1SC3=N[C@@H](C4=CC=CC=C4)CCN23
InChI key
ZMYZJAQMQBHNLH-CYBMUJFWSA-N
assay
≥95%
form
powder or chunks
mp
145-147 °C
functional group
phenyl, thioether
storage temp.
2-8°C
Quality Level
Related Categories
Application
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.
Other Notes
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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Alexander S Burns et al.
Organic letters, 19(11), 2953-2956 (2017-05-17)
A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion
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.
The Journal of organic chemistry, 78(9), 4594-4598 (2013-04-19)
A new implementation of the competing enantioselective conversion (CEC) method was developed to qualitatively determine the absolute configuration of enantioenriched secondary alcohols using thin-layer chromatography. The entire process for the method requires approximately 60 min and utilizes micromole quantities of
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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