(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate

Base Information

• Chemical Name: (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate
• CAS No.: 104197-95-7
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 104197-95-7.mol

Synonyms:(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate

Chemical Property of (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate

There total 13 articles about (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 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%

bromoacetic acid (-)-8-phenylmenthol ester (80595-59-1) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate (104197-95-7)

Guidance literature:

With silver nitrate; In acetonitrile;

DOI:10.1016/S0040-4039(00)86707-6

Reference yield: 73.0%

(1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate (71804-27-8) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate (104197-95-7)

Guidance literature:

With silver nitrate; In acetonitrile; for 42h; Darkness; Reflux;

DOI:10.1021/acs.orglett.5b00927

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate (104197-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / p-toluenesulfonic acid monohydrate / benzene / 11 h / Heating

2: 81 percent / AgNO₃ / acetonitrile / 94 h / Ambient temperature

With toluene-4-sulfonic acid; silver nitrate; In acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)90590-3

upstream raw materials:

bromoacetic acid (-)-8-phenylmenthol ester

(-)-8-phenylmenthol

(5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol

(-)-8-phenylmenthol phenylcarbamate

Downstream raw materials:

(-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate

(-)-8-phenylmenthyl (2S)-2-hydroxyoctanoate

(-)-8-phenylmenthyl (2S)-2-hydroxy-2-cyclohexylacetate

(-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

Refernces

• 1、 Hatano, Manabu,Yamashita, Kenji,Ishihara, Kazuaki. "C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles". supporting information. p. 2412 - 2415. Retrieved 2015/05/27.
• 2、 Whitesell, James K.,Bhattacharya, Apurba,Buchanan, Charles M.,Chen, H. H.,Deyo, Don,et al.. "ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL". . p. 2993 - 3002. Retrieved 2007/10/02.