N-(3-HYDROXY-4,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPT-2-YL)-4-METHYL-BENZENESULFONAMIDE

Base Information

• Chemical Name: N-(3-HYDROXY-4,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPT-2-YL)-4-METHYL-BENZENESULFONAMIDE
• CAS No.: 146387-13-5
• Molecular Formula: C17H25 N O3 S
• Molecular Weight: 323.4503
• Mol file: 146387-13-5.mol

Synonyms:Benzenesulfonamide,N-(3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-4-methyl-, [1S-(exo,exo)]-

Chemical Property of N-(3-HYDROXY-4,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPT-2-YL)-4-METHYL-BENZENESULFONAMIDE

Chemical Property:

• Vapor Pressure: 6.27E-09mmHg at 25°C
• Refractive Index: 1.589
• Boiling Point: 451.2°C at 760 mmHg
• PKA: 11.52±0.70(Predicted)
• Flash Point: 226.7°C
• PSA: 74.78000
• Density: 1.24g/cm³
• LogP: 3.93060

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(3-HYDROXY-4,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPT-2-YL)-4-METHYL-BENZENESULFONAMIDE

There total 1 articles about N-(3-HYDROXY-4,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPT-2-YL)-4-METHYL-BENZENESULFONAMIDE 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: 90.0%

(2S)-3-exo-aminoisoborneol (41719-73-7) + p-toluenesulfonyl chloride (98-59-9) → (1R,2S,3R,4S)-3-TsNH-1,7,7-(CH3)3-bicyclo[2.2.1]heptan-2-ol (146387-13-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/a902635e

Reference yield:

(1R,2S,3R,4S)-3-TsNH-1,7,7-(CH3)3-bicyclo[2.2.1]heptan-2-ol (146387-13-5) → (S)-2-Hydroxy-propionic acid (1R,2S,3R,4S)-1,7,7-trimethyl-3-(toluene-4-sulfonylamino)-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / Ambient temperature

2: 90 percent / LiAlH(OCEt₃)3 / tetrahydrofuran / 1 h / 0 °C

With pyridine; LiAlH(OCEt₃)3; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00057a004

Reference yield:

(1R,2S,3R,4S)-3-TsNH-1,7,7-(CH3)3-bicyclo[2.2.1]heptan-2-ol (146387-13-5) → (R)-Hydroxy-phenyl-acetic acid (1R,2S,3R,4S)-1,7,7-trimethyl-3-(toluene-4-sulfonylamino)-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / Ambient temperature

2: LiAlH(OCEt₃)3 / tetrahydrofuran / 1 h / 0 °C

With pyridine; LiAlH(OCEt₃)3; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00057a004

upstream raw materials:

(2S)-3-exo-aminoisoborneol

p-toluenesulfonyl chloride

Downstream raw materials:

2-Oxo-propionic acid (1R,2S,3R,4S)-1,7,7-trimethyl-3-(toluene-4-sulfonylamino)-bicyclo[2.2.1]hept-2-yl ester

(1R,2S,6R,7S)-4-Allyl-1,10,10-trimethyl-5-(toluene-4-sulfonyl)-3-oxa-5-aza-4-bora-tricyclo[5.2.1.0^2,6]decane

(S)-Hydroxy-phenyl-acetic acid (1R,2S,3R,4S)-1,7,7-trimethyl-3-(toluene-4-sulfonylamino)-bicyclo[2.2.1]hept-2-yl ester