Dihydroquinine

Dihydroquinine: Dihydroquinine

IUPAC name

(8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol

Identifiers

CAS number 522-66-7

PubChem 121515

ChemSpider 108426^Y

Jmol-3D images Image 1
Image 2

SMILES

O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43
O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C

InChI

InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1^Y
Key: LJOQGZACKSYWCH-WZBLMQSHSA-N^Y
InChI=1/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1
Key: LJOQGZACKSYWCH-WZBLMQSHBC

Properties

Molecular formula C₂₀H₂₆N₂O₂

Molar mass 326.43 g mol⁻¹

Melting point
173-175 °C

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Dihydroquinine, also known as hydroquinine,^[1] is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is -148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

See also

Dihydroquinidine

References

^ "Dihydroquinine chemical information". ChemIndustry.com. http://www.chemindustry.com/chemicals/560096.html.

Categories:
Alkaloids
Quinolines
Quinuclidines
Phenol ethers
Alcohols

Dihydroquinine

IUPAC name (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS number	522-66-7
PubChem	121515
ChemSpider	108426^Y
Jmol-3D images	Image 1 Image 2
SMILES O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43 O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C
InChI InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1^Y Key: LJOQGZACKSYWCH-WZBLMQSHSA-N^Y InChI=1/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1 Key: LJOQGZACKSYWCH-WZBLMQSHBC
Properties
Molecular formula	C₂₀H₂₆N₂O₂
Molar mass	326.43 g mol⁻¹
Melting point	173-175 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Alkaloid — This article is about the chemical compounds alkaloids. For the pharmaceutical company in the Republic of Macedonia see Alkaloid (company).Alkaloids are naturally occurring chemical compounds containing basic nitrogen atoms.… … Wikipedia
Cinchona — For other uses, see Cinchona (disambiguation). Cinchona Cinchona pubescens flowers Scientific classification Kingdom … Wikipedia
Dihydroquinidine — IUPAC name (9S) 10,11 Dihydro 6 methoxycinchonan 9 ol … Wikipedia
AD-mix — in organic chemistry is a commercially available mixture of reagents for performing amongst others the Sharpless asymmetric dihydroxylation of alkenes. The mix is available in two variations, AD mix α and AD mix β following ingredient lists… … Wikipedia
Asymmetric catalytic oxidation — is a technique of oxidizing various substrates to give an enantiopure product using a catalyst.Reactions*Jacobsen epoxidation of alkenes using manganese salen complex and NaOCl *Sharpless epoxidation of allyl alcohols using titanium isopropoxide … Wikipedia
Alcaloide — Alcaloïde Les alcaloïdes sont des molécules organiques hétérocycliques azotées d origine naturelle pouvant avoir une activité pharmacologique. Ce nom dérive du mot alcalin ; à l origine, le terme a été employé pour décrire n importe quelle… … Wikipédia en Français
Alcaloïde — Les alcaloïdes sont des molécules organiques hétérocycliques azotées basiques pouvant avoir une activité pharmacologique. À l origine, le terme a été employé pour décrire n importe quelle base de Lewis contenant un hétérocycle azoté (ou… … Wikipédia en Français
Alcaloïde polycyclique — Alcaloïde Les alcaloïdes sont des molécules organiques hétérocycliques azotées d origine naturelle pouvant avoir une activité pharmacologique. Ce nom dérive du mot alcalin ; à l origine, le terme a été employé pour décrire n importe quelle… … Wikipédia en Français

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Dihydroquinine

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Dihydroquinine

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