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392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

Synonyme(s) :

Hydroquinine 1,4-phthalazinediyl diether

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About This Item

Formule empirique (notation de Hill) :
C48H54N6O4
Numéro CAS:
140924-50-1
Poids moléculaire :
778.98
Beilstein:
5475677
Numéro MDL:
MFCD00191975
Code UNSPSC :
12352005
ID de substance PubChem :
24864480
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

≥95%

Activité optique

[α]22/D +336°, c = 1.2 in methanol

Pf

178 °C (dec.) (lit.)

Chaîne SMILES 

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

Clé InChI

YUCBLVFHJWOYDN-PPIALRKJSA-N

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Catégories apparentées

Description générale

DHQ)2PHAL is a modified cinchona alkaloid.[1]

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.[1]
  • As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.[2]
  • As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.[3]
Ligand for Sharpless Asymmetric Dihydroxylation employed in an enantioselective preparation of syn-3,5-hydroxycarboxylates from (E,E)- or (E,Z)-1,3-dienoates.[4]

Forme physique

Asymmetric dihydroxylation of unsaturated esters with trisubstituted C=C bonds.[5]

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H317

Conseils de prudence

P280 - P302 + P352

Classification des risques

Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF1096V
WXBD5623V
WXBD5386V
WXBD4931V
WXBD4545V

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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)
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.
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European Journal of Organic Chemistry, 9, 2119-2133 (2006)
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.

Contenu apparenté

Sharpless Group – Professor Product Portal

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

Questions

1–2 sur 2 questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 réponse

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 réponse

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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