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Merck
CN

499617

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide

90%

Synonym(s):

O(9)-Allyl-N-9-anthracenylcinchonidinium bromide, O(9)-Allyl-N-9-anthracenylmethylcinchonidium bromide, O-Allyl-1-(anthracen-9-ylmethyl)cinchonidinium bromide, O-Allyl-N-(9-anthracenylmethyl)cinchoninium bromide, O-Allyl-N-[(9-anthracenyl)methyl]cinchonidium bromide

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About This Item

Empirical Formula (Hill Notation):
C37H37BrN2O
CAS Number:
200132-54-3
Molecular Weight:
605.61
NACRES:
NA.22
PubChem Substance ID:
24873293
UNSPSC Code:
12352005
MDL number:
MFCD01632446

Key Documents

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InChI

1S/C37H37N2O.BrH/c1-3-21-40-37(33-17-19-38-35-16-10-9-15-32(33)35)36-23-27-18-20-39(36,24-26(27)4-2)25-34-30-13-7-5-11-28(30)22-29-12-6-8-14-31(29)34;/h3-17,19,22,26-27,36-37H,1-2,18,20-21,23-25H2;1H/q+1;/p-1/t26-,27-,36-,37+,39?;/m0./s1

SMILES string

[Br-].[H][C@@]12CC[N+](C[C@@H]1C=C)(Cc3c4ccccc4cc5ccccc35)[C@@]([H])(C2)[C@H](OCC=C)c6ccnc7ccccc67

InChI key

QOWNPAUSLGATNL-JNKXQCINSA-M

assay

90%

Quality Level

100

optical activity

[α]20/D −345±30°, c = 0.45 in chloroform

mp

170 °C (dec.) (lit.)

functional group

ether

Related Categories

General description

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is a cinchona-based chiral phase-transfer catalyst (PTC) that can be used in asymmetric synthesis. It can be prepared from N-(9-anthracenylmethyl)cinchonindinium chloride.

Application

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide can catalyze the asymmetric alkylation of tert-butyl glycinate-benzophenone Schiff base with different arylmethyl bromides in a micellar medium.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD5473
MKCC9485
MKBC4556V
MKBD5500V
MKBD5500

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Asymmetric Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions.
Okino T and Takemoto Y.
Organic Letters, 3(10), 1515-1517 (2001)
Preparation of O-Allyl-N-(9-Anthracenylmethyl) cinchonidinium Bromide as a Phase Transfer Catalyst for the Enantioselective Alkylation of Glycine Benzophenone Imine tert-Butyl Ester:(4S)-2-(Benzhydrylidenamino) pentanedioic Acid, 1-tert-Butyl Ester-5-Methyl Ester.
Corey EJ and Noe MC.
Organic Syntheses, 38-45 (2003)
Cinchona-based phase-transfer catalysts for asymmetric synthesis.
Jew SS and Park HG.
Chemical Communications (Cambridge, England), 46, 7090-7103 (2009)

Articles

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

Maruoka Catalysts

Maruoka catalysts enable enantioselective preparation of α-amino acids from glycine derivatives via asymmetric phase transfer catalysis.

金鸡纳生物碱

不对称相转移催化（PTC）已被公认为是许多均相合成有机转化的“绿色”替代方法，并且已被广泛应用。合成修饰的金鸡纳生物碱是用于不对称PTC的典型手性有机催化剂。

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