(1R,2R,5S)-Neomenthyl azide

Base Information

• Chemical Name: (1R,2R,5S)-Neomenthyl azide
• CAS No.: 259826-43-2
• Molecular Formula: C10H19N3
• Molecular Weight: 181.27800
• DSSTox Substance ID: DTXSID70470372
• Nikkaji Number: J659.454I
• Mol file: 259826-43-2.mol

Synonyms:(1R,2R,5S)-Neomenthyl azide;259826-43-2;(1R,2R,4S)-2-azido-4-methyl-1-propan-2-ylcyclohexane;DTXSID70470372;AKOS006344804;(1R, 2R, 5S)-NEOMENTHYL AZIDE;(1R, 2R, 4S)-2-azido-4-methyl-1-propan-2-ylcyclohexane

Chemical Property of (1R,2R,5S)-Neomenthyl azide

Chemical Property:

• PSA: 49.75000
• LogP: 3.21026
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 181.157897619
• Heavy Atom Count: 13
• Complexity: 206

Purity/Quality:

97% ^*data from raw suppliers

(1R,2R,5S)-NEOMENTHYL AZIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)N=[N+]=[N-])C(C)C
• Isomeric SMILES: C[C@H]1CC[C@@H]([C@@H](C1)N=[N+]=[N-])C(C)C

Technology Process of (1R,2R,5S)-Neomenthyl azide

There total 4 articles about (1R,2R,5S)-Neomenthyl azide 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%

(1S,2R,5S)-2-i-propyl-5-methylcyclohexyl 4-methylbenzenesulfonate (959925-33-8) → (1S,3R,4R)-3-azidomenthane (259826-43-2,898543-45-8,898543-46-9)

Guidance literature:

With trimethylsilylazide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70 ℃; for 168h;

DOI:10.1055/s-1995-3928

Reference yield: 76.0%

(-)-menthol (2216-51-5) → (1S,3R,4R)-3-azidomenthane (259826-43-2,898543-45-8,898543-46-9)

Guidance literature:

With zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; Ambient temperature;

DOI:10.1055/s-1990-26809

Reference yield: 65.0%

(1S,2R,5S)-(+)-menthol (15356-60-2) → (1S,3R,4R)-3-azidomenthane (259826-43-2,898543-45-8,898543-46-9)

Guidance literature:

With nicotinoyl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1055/s-2004-831254

upstream raw materials:

menthyl tosylate

(-)-menthol

(1S,2R,5S)-2-i-propyl-5-methylcyclohexyl 4-methylbenzenesulfonate

(1S,2R,5S)-(+)-menthol

Downstream raw materials:

N-((1S)-neomenthyl)-formamide

C₁₁H₁₉N

(1R,2R,4S) 1-isopropyl-4-methyl-2-nitrocyclohexane

(+)-neomenthylamine

Refernces

• 1、 Papeo, Gianluca,Posteri, Helena,Vianello, Paola,Varasi, Mario. "Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: An expedient one-pot transformation of alcohols into azides". . p. 2886 - 2892. Retrieved 2007/10/03.
• 2、 Viaud, Marie Claude,Rollin, Patrick. "Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols". . p. 130 - 132. Retrieved 2007/10/02.