(+)-alpha-Conhydrine

Base Information

• Chemical Name: (+)-alpha-Conhydrine
• CAS No.: 495-20-5
• Molecular Formula: C8H17 N O
• Molecular Weight: 143.229
• Hs Code.: 2933399090
• European Community (EC) Number: 207-798-1
• Nikkaji Number: J1.303.866J
• Wikipedia: Conhydrine
• Mol file: 495-20-5.mol

Synonyms:alpha-conhydrine;conhydrine

Chemical Property of (+)-alpha-Conhydrine

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C
• Melting Point: 121°
• Refractive Index: 1.4852 (estimate)
• Boiling Point: 226.7°Cat760mmHg
• PKA: 15.15±0.20(Predicted)
• Flash Point: 82.3°C
• PSA: 32.26000
• Density: 0.941g/cm³
• LogP: 1.22820
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 143.131014166
• Heavy Atom Count: 10
• Complexity: 95.3

Purity/Quality:

99% ^*data from raw suppliers

CONHYDRINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1CCCCN1)O
• Isomeric SMILES: CC[C@H]([C@H]1CCCCN1)O

Technology Process of (+)-alpha-Conhydrine

There total 96 articles about (+)-alpha-Conhydrine 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: 95.0%

conhydrinone hydrochloride (38726-77-1) → C8H17NO (63401-12-7) + (+)-conhydrine (495-20-5)

Guidance literature:

With RuCl₂[(R)-XylSDP][(S,S)-DPEN]; potassium tert-butylate; hydrogen; In isopropyl alcohol; at 20 ℃; under 38002.6 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/ol901605a

Reference yield: 88.0%

O-benzylconhydrine (127628-03-9) → (+)-conhydrine (495-20-5)

Guidance literature:

With hydrogen; hydrogenchloride; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(01)93904-8

Reference yield: 88.0%

(4S,5R)-5-Ethyl-4-(4-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (854778-92-0) + methanesulfonyl chloride (124-63-0) → (+)-conhydrine (495-20-5)

Guidance literature:

(4S,5R)-5-Ethyl-4-(4-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; methanesulfonyl chloride; With triethylamine; at -78 ℃; for 1h;

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2005.04.013

upstream raw materials:

O-benzylconhydrine

(1R,8aS)-1-Ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

(4S,5R)-5-Ethyl-4-(4-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

methanesulfonyl chloride

Downstream raw materials:

(6S)-8t-methyl-(6rH)-1-aza-bicyclo[4.2.0]octane

(-)-2-cis-propenyl-piperidine

(-)-2-trans-propenyl-piperidine

6-propyl-2,3,4,5-tetrahydropyridine

Refernces

• 1、 Pandey, Satyendra Kumar,Kumar, Pradeep. "Stereoselective syntheses of (+)-α- and (-)-β-conhydrine from L-aspartic acid". . p. 4091 - 4093. Retrieved 2005.
• 2、 Dong, Guang Ri,Hong, Seungmin,Kim, Seung In,Kim, In Su,Jung, Young Hoon. "Stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue". . p. 4200 - 4205. Retrieved 2012/10/07.
• 3、 Shaikh, Tanveer Mahamadali,Sudalai, Arumugam. "Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation". experimental part. p. 3437 - 3444. Retrieved 2010/08/20.