Skip to Content
Merck
CN

Key Documents

View All Documentation

392723

(DHQ)2PHAL

≥95%

Synonym(s):

Hydroquinine 1,4-phthalazinediyl diether

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C48H54N6O4
CAS Number:
140924-50-1
Molecular Weight:
778.98
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24864480
MDL number:
MFCD00191975
Beilstein/REAXYS Number:
5475677
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

200

assay

≥95%

optical activity

[α]22/D +336°, c = 1.2 in methanol

mp

178 °C (dec.) (lit.)

SMILES string

CC[C@@H]1CN2CCC1CC2[C@H](Oc3nnc(O[C@@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10

InChI

1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30+,31-,32+,43-,44-,45-,46-/m1/s1

InChI key

YUCBLVFHJWOYDN-PPIALRKJSA-N

General description

DHQ)2PHAL is a modified cinchona alkaloid.

Application

(DHQ)2PHAL may be used in the following processes:
  • As a catalyst Asymmetric and chemoselective N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates to form pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.
  • As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.
  • As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.
Ligand for Sharpless Asymmetric Dihydroxylation employed in an enantioselective preparation of syn-3,5-hydroxycarboxylates from (E,E)- or (E,Z)-1,3-dienoates.

Physical form

Asymmetric dihydroxylation of unsaturated esters with trisubstituted C=C bonds.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

Regulatory Information

新产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF7364V
WXBF1096V
WXBD5623V
WXBD5386V
WXBD4931V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.

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。

Related Content

Sharpless Group – Professor Product Portal

The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.

From styrenes to enantiopure a-arylglycines in two steps.
Reddy KL and Sharpless KB.
Journal of the American Chemical Society, 120(6), 1207-1217 (1990)
Kapferer, Tobias; Brueckner, Reinhard
European Journal of Organic Chemistry, 9, 2119-2133 (2006)
Chemoselective Asymmetric N-Allylic Alkylation of Indoles with Morita-Baylis-Hillman Carbonates.
Cui H-L, et al.
Angewandte Chemie (International Edition in English), 48(31), 5737-5740 (2009)
View All Related Papers

Global Trade Item Number

SKUGTIN
392723-500MG04061831981681