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392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

Sinónimos:

Hydroquinine 1,4-phthalazinediyl diether

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About This Item

Fórmula empírica (notación de Hill):
C48H54N6O4
Número de CAS:
140924-50-1
Peso molecular:
778.98
Beilstein:
5475677
Número MDL:
MFCD00191975
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
24864480
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

200

Ensayo

≥95%

actividad óptica

[α]22/D +336°, c = 1.2 in methanol

mp

178 °C (dec.) (lit.)

cadena 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

Clave InChI

YUCBLVFHJWOYDN-PPIALRKJSA-N

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Descripción general

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

Aplicación

(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]

Forma física

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

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H317

Consejos de prudencia

P280 - P302 + P352

Clasificaciones de peligro

Skin Sens. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
WXBF1096V
WXBD5623V
WXBD5386V
WXBD4931V
WXBD4545V

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Troger’s Base 98%

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Troger′s Base

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)
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)
Kapferer, Tobias; Brueckner, Reinhard
European Journal of Organic Chemistry, 9, 2119-2133 (2006)
Regioselective Oxidative Cleavage of Benzylidene Acetals: Synthesis of a-and ?-Benzoyloxy Carboxylic Acids.
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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

Artículos

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.

Contenido relacionado

Sharpless Group – Professor Product Portal

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

Questions

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  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

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  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

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