374482
N-苄基奎宁氯
95%
别名:
QUIBEC
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关于此项目
经验公式（希尔记法）:
C27H31ClN2O2
化学文摘社编号:
分子量:
451.00
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
5702637
InChI
1S/C27H31N2O2.ClH/c1-3-20-18-29(17-19-7-5-4-6-8-19)14-12-21(20)15-26(29)27(30)23-11-13-28-25-10-9-22(31-2)16-24(23)25;/h3-11,13,16,20-21,26-27,30H,1,12,14-15,17-18H2,2H3;1H/q+1;/p-1/t20-,21-,26-,27+,29+;/m0./s1
SMILES string
[Cl-].COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@+]3(C[C@@H]4C=C)Cc5ccccc5)c2c1
InChI key
JYDIJFKNXHPWBJ-GOGFHWEMSA-M
assay
95%
Quality Level
form
powder
optical activity
[α]20/D −235°, c = 1.5 in H2O
mp
200-205 °C (dec.) (lit.)
functional group
hydroxyl, phenyl
General description
N-Benzylquininium chloride (or Quibec) belongs to the class of cinchona family of alkaloids. It is used as a catalyst in the presence of hydroxide bases in various phase transfer reactions, epoxidations, alkylations, and Michael reactions.
Application
N-Benzylquininium chloride can be used as a phase transfer catalyst:
- In the sulfenylation of various β-keto sulfoxides.
- To synthesize N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Sulfenylation of β-keto sulfoxides. III. Diastereoselectivity induced by a chiral phase transfer catalyst
Wladislaw B, et al.
Tetrahedron, 55(41), 12023-12030 (1999)
Phase-Transfer-Catalyzed Asymmetric Aza-Henry Reaction Using N-Carbamoyl Imines Generated In Situ from ?-Amido Sulfones
Fini F, et al.
Angewandte Chemie (International ed. in English), 44(48), 7975-7978 (2005)
N-Benzylquininium Chloride
Bos Mary E, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-7 (2001)
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