3-Quinuclidinol

Base Information

• Chemical Name: 3-Quinuclidinol
• CAS No.: 1619-34-7
• Deprecated CAS: 29924-74-1,3684-26-2
• Molecular Formula: C7H13NO
• Molecular Weight: 127.186
• Hs Code.: 29333920
• European Community (EC) Number: 216-578-4
• NSC Number: 93905
• UNII: 974MVZ0WOK
• DSSTox Substance ID: DTXSID50862716
• Nikkaji Number: J84.997I
• Wikidata: Q27197086
• Metabolomics Workbench ID: 66887
• ChEMBL ID: CHEMBL276310
• Mol file: 1619-34-7.mol

Synonyms:3-quinuclidinol

Chemical Property of 3-Quinuclidinol

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 0.0545mmHg at 25°C
• Melting Point: 220-223 °C(lit.)
• Refractive Index: 1.4790 (estimate)
• 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.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: soluble
• 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:

99.9% ^*data from raw suppliers

3-Quinuclidinol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)O
• Uses: Hypotensive. Synthon for preparation of cholinergic receptor ligands and anesthetics 3-Quinuclidinol acts as a chiral building block for various antimuscarinic agents and other active pharmaceutical ingredients. It serves as a catalyst for condensation of methyl vinyl ketone with aldehydes. It is also used as a reagent for cleavage of beta-keto and vinylogous beta-keto esters. Further, it plays an important role as a synthon in the preparation of cholinergic receptor ligands and anesthetics. In addition to this, it is used in chemoselective alfa-iodination of acrylic esters through Morita-Baylis-Hillman reaction.

Technology Process of 3-Quinuclidinol

There total 34 articles about 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:

(-)-Aceclidine

(S)-quinuclidin-3-yl benzoate

quinuclidin-3-yl butyrate b

isobutyric acid 1-aza-bicyclo[2.2.2]oct-3-yl ester

Downstream raw materials:

3-(Diphenylacetyloxy)quinuclidine

3-acetoxyquinuclidine

quinuclidin-3-yl tosylate

1-azabicyclo[2.2.2]oct-2-ene

Refernces

• 1、 Wang, Yu,Li, Jianjiong,Wu, Qiaqing,Zhu, Dunming. "Microbial stereospecific reduction of 3-quinuclidinone with newly isolated Nocardia sp. and Rhodococcus erythropolis". . p. 14 - 19. Retrieved 2013.
• 2、 LEVINE,DIASSI. "A-NORSTEROIDS. KETALIZATION OF A-NORTESTOSTERONE.". . p. 1325 - 1327. Retrieved 1965.
• 3、 Primozic, Ines,Hrenar, Tomica,Tomic, Srdanka,Meic, Zlatko. "Interactions of chiral quinuclidin-3-yl benzoates with butyrylcholinesterase: Kinetic study and docking simulations". . p. 608 - 614. Retrieved 2002.
• 4、 Chen, Hao-Ping,Ho, Tsung-Jung,Hung, Chien-Chi,Khine, Aye Aye,Lu, Pei-Chieh,Simaremare, Sailent Rizki Sari,Tung, Chi-Hua,Wu, Jia-Ru,Yiin, Lin-Ming. "Borneol dehydrogenase from Pseudomonas sp. TCU-HL1 possesses novel quinuclidinone reductase activities". . . Retrieved 2021/08/30.
• 5、 -. "Preparation method of optical activity 3-quinuclidinol". . . Retrieved 2018/04/03.