Direkt zum Inhalt
Merck

392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

Synonym(e):

Hydrochinin-1,4-phthalazindiyl-diether

Anmeldenzur Ansicht organisationsspezifischer und vertraglich vereinbarter Preise


About This Item

Empirische Formel (Hill-System):
C48H54N6O4
CAS-Nummer:
Molekulargewicht:
778.98
Beilstein:
5475677
MDL-Nummer:
UNSPSC-Code:
12352005
PubChem Substanz-ID:
NACRES:
NA.22
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Qualitätsniveau

Assay

≥95%

Optische Aktivität

[α]22/D +336°, c = 1.2 in methanol

mp (Schmelzpunkt)

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

InChIKey

YUCBLVFHJWOYDN-PPIALRKJSA-N

Suchen Sie nach ähnlichen Produkten? Aufrufen Leitfaden zum Produktvergleich

Allgemeine Beschreibung

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

Anwendung

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

Physikalische Form

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

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Skin Sens. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type N95 (US)


Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number

Die passende Version wird nicht angezeigt?

Wenn Sie eine bestimmte Version benötigen, können Sie anhand der Lot- oder Chargennummer nach einem spezifischen Zertifikat suchen.

Besitzen Sie dieses Produkt bereits?

In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Kunden haben sich ebenfalls angesehen

Slide 1 of 2

1 of 2

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)
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)
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

Artikel

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.

Verwandter Inhalt

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

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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

      Helpful?

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

    1 answer
    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

      Helpful?

Reviews

No rating value

Active Filters

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

Setzen Sie sich mit dem technischen Dienst in Verbindung.