(1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol

Base Information

• Chemical Name: (1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol
• CAS No.: 29900-93-4
• Molecular Formula: C10H19 N O
• Molecular Weight: 169.267
• European Community (EC) Number: 249-941-0
• DSSTox Substance ID: DTXSID401313094
• Nikkaji Number: J413.886D
• Mol file: 29900-93-4.mol

Synonyms:29900-93-4;EINECS 249-941-0;(1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol;(1R,2R,3S,4S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol;[1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol;Bicyclo(2.2.1)heptan-2-ol, 3-amino-1,7,7-trimethyl-, (1R-(2-endo,3-exo))-;DTXSID401313094;AKOS006312881;(1R,4alpha)-1,7,7-Trimethyl-3beta-aminobicyclo[2.2.1]heptan-2beta-ol

Chemical Property of (1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol

Chemical Property:

• Vapor Pressure: 0.00797mmHg at 25°C
• Boiling Point: 237.5°Cat760mmHg
• Flash Point: 97.4°C
• PSA: 46.25000
• Density: 1.038g/cm³
• LogP: 1.83100
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 169.146664230
• Heavy Atom Count: 12
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

(1R)-3-endo-Aminoborneol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2N)O)C)C
• Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)[C@@H]([C@@H]2O)N

Technology Process of (1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol

There total 25 articles about (1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol 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: 98.0%

(1R,2R,6S,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0(2,6)]decan-4-one (41719-63-5) → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4)

Guidance literature:

With water; sodium hydroxide; In ethanol; for 6h; optical yield given as %de; Reflux;

DOI:10.1055/s-0030-1258355

Reference yield: 83.0%

(3aS,4S,7R,7aR)-2-phenyl-7,8,8-trimethyl-3a,4,5,6,7,7a-hexahydro-4,7-methanobenzoxazole → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 21h; Product distribution; other benzoylated bornanes; other temperatures;

Reference yield:

(1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (663-17-2,5338-41-0,13854-86-9,13854-87-0,22472-58-8,31571-14-9,103833-77-8) → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + (2S)-3-exo-aminoisoborneol (41719-73-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃;

DOI:10.1248/cpb.49.1018

upstream raw materials:

3-amino-bornan-2-one

3-endo-aminobornan-2-one

(1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane

N-<(1R,2R,3S,4S)-2-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-3-yl>-benzamide

Downstream raw materials:

(1R,2R,3S,4S)-3-(4-vinylbenzenesulfonyl)amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Benzyl-((1S,2S,6R)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-ylmethyl)-amine

(1S,2S,6R)-1,10,10-Trimethyl-4-phenylselanylmethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

4-Methyl-N-((1S,2S,6R)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-ylmethyl)-benzenesulfonamide

Refernces

• 1、 Campbell, Craig D.,Concellon, Carmen,Smith, Andrew D.. "Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes". experimental part. p. 797 - 811. Retrieved 2011/08/06.
• 2、 Shimizu, Makoto,Teramoto, Yoshihiro,Fujisawa, Tamotsu. "CREATION OF CHIRALITY IN THE REACTION OF THE CHIRAL ESTER ENOLATE-IMINE CONDENSATION LEADING TO THE STEREODIVERGENT SYNTHESIS OF β-LACTAMS". . p. 729 - 732. Retrieved 2007/10/02.