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392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

Synonym(s):

Hydroquinine 1,4-phthalazinediyl diether

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About This Item

Empirical Formula (Hill Notation):
C48H54N6O4
CAS Number:
140924-50-1
Molecular Weight:
778.98
Beilstein:
5475677
MDL number:
MFCD00191975
UNSPSC Code:
12352005
PubChem Substance ID:
24864480
NACRES:
NA.22

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

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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

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280 - P302 + P352

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

392723-VAR:
392723-500MG:
392723-BULK:
392723-50G:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD5623V
WXBD5386V
WXBD4931V
WXBD4545V
WXBD1723V

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Kapferer, Tobias; Brueckner, Reinhard
European Journal of Organic Chemistry, 9, 2119-2133 (2006)
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)
Regioselective Oxidative Cleavage of Benzylidene Acetals: Synthesis of a-and ?-Benzoyloxy Carboxylic Acids.
Kumar PS, et al.
Angewandte Chemie (International Edition in English), 49(4), 804-807 (2010)
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)
Md Moinuddin Ahmed et al.
The Journal of organic chemistry, 71(20), 7741-7746 (2006-09-26)
The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting

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.

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