(R)-(-)-3-Quinuclidinol

Base Information

• Chemical Name: (R)-(-)-3-Quinuclidinol
• CAS No.: 25333-42-0
• Molecular Formula: C7H13NO
• Molecular Weight: 127.186
• Hs Code.: 29339980
• European Community (EC) Number: 246-857-6
• UNII: 19XL022LM3
• DSSTox Substance ID: DTXSID50179977
• Nikkaji Number: J1.522.071F,J254.859C
• Wikidata: Q27252136
• Mol file: 25333-42-0.mol

Synonyms:(R)-(-)-3-Quinuclidinol;25333-42-0;(R)-Quinuclidin-3-ol;(3R)-1-azabicyclo[2.2.2]octan-3-ol;(R)-3-QUINUCLIDINOL;(3r)-quinuclidin-3-ol;3-Quinuclidinol l-form;R-(-)-3-Quinuclidinol;3(R)-quinuclidinol;(R)-3-Quinuclidol;3-(R)-quinuclidinol;1-Azabicyclo[2.2.2]octan-3-ol, (3R)-;3-Quinuclidinol, (-)-;C7H13NO;UNII-19XL022LM3;(R)-(-)-quinuclidin-3-ol;19XL022LM3;EINECS 246-857-6;MFCD00211251;EC 246-857-6;l-3-Quinuclidinol;(-)-3-Quinuclidinol;(R)-(-)-1-Azabicyclo[2.2.2]octan-3-ol;1-AZABICYCLO(2.2.2)OCTAN-3-OL, (3R)-;(R)-(-)-1-AZABICYCLO(2.2.2)OCTAN-3-OL;(R)-3-Hydroxyquinuclidine;(?)-3-Qinuclidinol;(3R)-3-Quinuclidinol;(R)-quinuclidine-3-ol;(R) -quinuclidin-3-ol;(R)-(3)-quinuclidinol;3-Quinuclidinol R isomer;3-(R)-Hydroxyquinuclidine;3-(R)-Hydroxy-quinuclidine;SCHEMBL71473;R-(-)-3-Hydroxyquinuclidine;(3R)-(-)-quinuclidin-3-ol;SCHEMBL21087936;NARONAPRIDE METABOLITE M5;DTXSID50179977;(1S,3R,4S)-quinuclidin-3-ol;AMY39446;BCP10791;CS-B0280;3-QUINUCLIDINOL L-FORM [MI];MFCD13191732;AKOS005255229;AKOS015907653;AC-4632;(r)-1-azabicyclo[2.2.2]octan-3-ol;AS-11397;R-(-)-Azabicyclo[2.2.2]octane-3-ol;(R)-1-Aza-bicyclo[2.2.2]octan-3-ol;R-(-)-Quinuclidin-3-ol;NSC 93905;1-Azabicyclo(2.2.2)octan-3-ol, (R)-;3-(R)-hydroxy-1-azabicyclo[2.2.2]octane;A5118;(3R)-3-hydroxy-1-azabicyclo[2.2.2]octane;(R)-quinuclidin-3-ol;R-(-)-3-Hydroxy-1-azabicyclo[2.2.2]octane;Q-101002;Q27252136;(3R)-1-Azabicyclo[2.2.2]octan-3-ol ((3R)-3-Quinuclidinol)

Chemical Property of (R)-(-)-3-Quinuclidinol

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.0545mmHg at 25°C
• Melting Point: 217-224 °C
• Refractive Index: 1.549
• Boiling Point: 206.9 °C at 760 mmHg
• PKA: 14.75±0.20(Predicted)
• Flash Point: 97.7 °C
• PSA: 23.47000
• Density: 1.13 g/cm₃
• LogP: 0.01080
• Storage Temp.: Flammables area
• Water Solubility.: 100 g/100 mL
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 127.099714038
• Heavy Atom Count: 9
• Complexity: 108

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-3-Quinuclidinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C
• Hazard Codes: C-F,C,F
• Statements: 34-11
• Safety Statements: 45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)O
• Isomeric SMILES: C1CN2CCC1[C@H](C2)O
• General Description: (R)-(-)-3-Quinuclidinol is a valuable chiral building block widely used in the synthesis of pharmaceuticals, particularly antimuscarinic agents. It can be efficiently produced via biocatalytic reduction of 3-quinuclidinone using highly enantioselective reductases such as AtQR, KaKR, or KgQR, which exhibit strong substrate-binding affinity and high catalytic efficiency. Alternatively, fungal-mediated reduction (e.g., *Mucor piriformis*) and asymmetric hydrogenation using ruthenium catalysts (e.g., XylSkewphos/PICA-Ru(II)) also yield (R)-3-Quinuclidinol with high enantiomeric purity. These methods enable scalable production, with whole-cell biocatalysts achieving high space-time yields (e.g., 1027 g·L^?1·d^?1) and industrial feasibility. Key residues (e.g., Glu197 in AtQR, E198 in KaKR) contribute to substrate orientation and enantioselectivity, while robust enzymes like KgQR tolerate high substrate concentrations (up to 5.0 M) without requiring external cofactors.

Technology Process of (R)-(-)-3-Quinuclidinol

There total 53 articles about (R)-(-)-3-Quinuclidinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3-Quinuclidinone (3731-38-2) → (S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7)

Guidance literature:

With RuCl[(S)-daipena][(S)-3,5-xylyl-BINAP]; potassium tert-butylate; hydrogen; In isopropyl alcohol; at 10 ℃; for 6h; under 22801.5 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja202296w

Reference yield: 92.0%

3-quinuclidinone hydrochloride (1193-65-3) → (S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7)

Guidance literature:

With D-glucose; In aq. phosphate buffer; at 30 ℃; for 48h; pH=8; Concentration; Temperature; pH-value; Time;

DOI:10.1016/j.molcatb.2012.11.013

Reference yield: 86.0%

(3S)-1-azabicyclo[2.2.2]oct-3-yl benzoate (D)-tartrate → (S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

3-quinuclidinol

(-)-Aceclidine

(S)-quinuclidin-3-yl benzoate

quinuclidin-3-yl butyrate b

Downstream raw materials:

9H-Xanthene-9-carboxylic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

(S)-2-Hydroxy-2-phenyl-propionic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

(R)-2-Hydroxy-2-phenyl-propionic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

3(S)-<<(3-oxo-4(R),7,7-trimethyl-2-oxabicyclo<2.2.1>hept-1(S)-yl)carbonyl>oxy>-1-azabicyclo<2.2.2>octane