149725-81-5

Basic information

• Product Name: (DHQD)2PYR
• Synonyms: HYDROQUINIDINE 2,5-DIPHENYL-4,6-PYRIMIDINEDIYL DIETHER;(DHQD)2PYR;(DHQD)2Pyr,Hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether;2,5-Diphenyl-4,6-bis(dihydroquinidine)pyrimidine;(DHQD)2Pyr 97%;Cinchonan,9,9''-[(2,5-diphenyl-4,6-pyrimidinediyl)bis(oxy)]bis[10,11-dihydro-6'-methoxy-,(9S,9''S)-;Hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl Diether,99%e.e.;6,6-((1S)-((2,5-Diphenylpyrimidine-4,6-diyl)bis(oxy))bis((6-methoxyquinolin-4-yl)methylene))bis(3-vinylquinuclidine)
• CAS NO: 149725-81-5
• Molecular Formula: C56H60N6O4
• Molecular Weight: 881.11
• Mol File: 149725-81-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 247-250 °C(lit.)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Refractive Index: 1.69
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.50±0.70(Predicted)
• CAS DataBase Reference: (DHQD)2PYR(CAS DataBase Reference)
• NIST Chemistry Reference: (DHQD)2PYR(149725-81-5)
• EPA Substance Registry System: (DHQD)2PYR(149725-81-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 149725-81-5(Hazardous Substances Data)

Usage

Description

(DHQD)2PYR, also known as Dihydroquinine, is a chiral catalyst derived from quinine, a natural alkaloid found in the bark of the cinchona tree. It is a versatile and widely used reagent in organic synthesis, particularly in asymmetric catalysis. Its unique structure allows for the formation of stable complexes with various substrates, making it a valuable tool in the development of enantioselective reactions.

Uses

Used in Chemical Synthesis:
(DHQD)2PYR is used as a chiral catalyst for the enantioselective allylic amination of alkylidene cyanoacetates with dialkyl azodicarboxylates. This reaction is crucial in the synthesis of various pharmaceutical compounds and natural products, as it allows for the selective formation of chiral amines with high enantiomeric purity.
Used in Asymmetric Dihydroxylation:
(DHQD)2PYR is used as a catalyst in the Sharpless catalytic asymmetric dihydroxylation, a reaction that allows for the selective formation of 10(R),11-Dihydroxydihydroquinine and 10(S),11-dihydroxydihydroquinine. These diols are important intermediates in the synthesis of various biologically active compounds, including pharmaceuticals and agrochemicals.
Used in Total Synthesis:
(DHQD)2PYR is used in the total synthesis of okadaic acid, a potent protein phosphatase inhibitor. Okadaic acid has various applications in cell biology and pharmacology, as it can modulate cellular signaling pathways and has been used as a tool to study the role of protein phosphatases in various cellular processes.

InChI:InChI=1/C56H60N6O4/c1-5-35-33-61-27-23-39(35)29-49(61)52(43-21-25-57-47-19-17-41(63-3)31-45(43)47)65-55-51(37-13-9-7-10-14-37)56(60-54(59-55)38-15-11-8-12-16-38)66-53(50-30-40-24-28-62(50)34-36(40)6-2)44-22-26-58-48-20-18-42(64-4)32-46(44)48/h7-22,25-26,31-32,35-36,39-40,49-50,52-53H,5-6,23-24,27-30,33-34H2,1-4H3/t35-,36-,39-,40-,49+,50?,52-,53-/m0/s1