684341
(S)-5-(吡咯烷-2-基)-1H-四唑
96%
别名:
(S)-(–)-2-四唑-5-基吡咯烷, 脯氨酸四唑催化剂
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关于此项目
经验公式（希尔记法）:
C5H9N5
化学文摘社编号:
分子量:
139.16
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
产品名称
(S)-5-(吡咯烷-2-基)-1H-四唑, 96%
InChI
1S/C5H9N5/c1-2-4(6-3-1)5-7-9-10-8-5/h4,6H,1-3H2,(H,7,8,9,10)/t4-/m0/s1
SMILES string
C1CN[C@@H](C1)c2nnn[nH]2
InChI key
XUHYQIQIENDJER-BYPYZUCNSA-N
assay
96%
form
solid
optical activity
[α]20/D -9.0°, c = 1 in methanol
mp
253-258 °C
Quality Level
Application
(S)-(−)-5-(2-Pyrrolidinyl)-1H-tetrazole can be used as an organocatalyst:
- To prepare enantioselective chiral 1,2-oxazines from achiral ketones via an intramolecular Wittig reaction.
- To synthesize diastereoselective Michael addition products by addition of aliphatic aldehydes to β-nitrostyrene.
- In the direct asymmetric α-fluorination of linear and branched aldehydes using N-fluorobenzenesulfonamide as the fluorinating agent.
Organocatalyst used for:
- Direct asymmetric aldol reactions between acetone and aldehydes yielding β -hydroxy ketone and for synthesizing 1,1,1-trichloro-2-alkanols
- Mannich reactions for synthesis fo α -amino acids and generation of 1,4-diamines
- Conjugate additions of malonates to enones
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Oelke, A. et al.
Synlett, 2548-2548 (2006)
Asymmetric organocatalyzed Michael addition of aldehydes to β-nitrostyrene in ionic liquids
Mevciarova M, et al.
Tetrahedron Asymmetry, 20(20), 2403-2406 (2009)
Sirirat Kumarn et al.
Chemical communications (Cambridge, England), (30), 3211-3213 (2006-10-10)
A sequential, organocatalysed asymmetric reaction to access chiral 1,2-oxazines from achiral ketone starting materials is reported, which proceeds in moderate to good yields and excellent enantioselectivity.
Direct asymmetric α-fluorination of aldehydes
Steiner DD, et al.
Angewandte Chemie (International Edition in English), 117(24), 3772-3776 (2005)
A highly selective, organocatalytic route to chiral 1, 2-oxazines from ketones
Kumarn S, et al.
Chemical Communications (Cambridge, England), 3211-3213 (2006)
相关内容
The Yamamoto group has employed several applications in catalysis.
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