(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:

98%, ^*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
• Uses: Hypotensive. Synthon for preparation of cholinergic receptor ligands and anesthetics Sitagliptin phosphate?intermediate

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:

(S)-1-Butyl-3-hydroxy-1-azonia-bicyclo[2.2.2]octane; bromide

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

(R)-QNX

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

Refernces

• 1、 Kolet, Swati P.,Jadhav, Dipesh D.,Priyadarshini, Balaraman,Swarge, Bhagyashree N.,Thulasiram, Hirekodathakallu V.. "Fungi mediated production and practical purification of (R)-(-)-3-quinuclidinol". . p. 5911 - 5914. Retrieved 2014.
• 2、 Arai, Noriyoshi,Kurono, Nobuhito,Ohkuma, Takeshi,Tsutsumi, Kunihiko,Katayama, Takeaki,Utsumi, Noriyuki,Murata, Kunihiko. "Practical asymmetric hydrogenation of 3-quinuclidinone catalyzed by the xylskewphos/PICA-ruthenium(II) complex". . p. 625 - 628. Retrieved 2009.
• 3、 Chen, Qian,Xie, Baogang,Zhou, Liping,Sun, Lili,Li, Shanshan,Chen, Yuhan,Shi, Shan,Li, Yang,Yu, Mingan,Li, Wei. "A Tailor-Made Self-Sufficient Whole-Cell Biocatalyst Enables Scalable Enantioselective Synthesis of (R)-3-Quinuclidinol in a High Space-Time Yield". . p. 1813 - 1821. Retrieved 2019.
• 4、 Chen, Xiaoyu,Dou, Zhe,Luo, Tianwei,Ni, Ye,Sun, Zewen,Xu, Guochao. "A novel and robust 3-quinuclidinone reductase from Kaistia algarum for efficient synthesis of (R)-3-quinuclidinol without external cofactor". . . Retrieved 2021/09/28.