(alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol

Base Information

• Chemical Name: (alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol
• CAS No.: 154920-05-5
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.285
• DSSTox Substance ID: DTXSID301244048
• Mol file: 154920-05-5.mol

Synonyms:DTXSID301244048;(alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol;154920-05-5

Chemical Property of (alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 190.135765193
• Heavy Atom Count: 14
• Complexity: 159

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)C(CC=C)O
• Isomeric SMILES: C[C@H](CC1=CC=CC=C1)[C@@H](CC=C)O

Technology Process of (alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol

There total 8 articles about (alphaR,betaR)-beta-Methyl-alpha-2-propen-1-ylbenzenepropanol 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%

(2R)-2-methyl-3-phenylpropanal (5445-77-2,63262-79-3,78964-59-7,42307-59-5) + (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole (547713-49-5) → (2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol (154920-05-5)

Guidance literature:

In dichloromethane; at -10 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja808347q

Reference yield:

(4R,5S,6R)-4-Allyl-2,2,5-trimethyl-6-phenyl-[1,3]dioxane (154920-04-4) → (2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol (154920-05-5)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -60 ℃;

DOI:10.1016/S0040-4039(00)61344-8

Reference yield:

(2R,3R)-3-Hydroxy-N-methoxy-2,N-dimethyl-3-phenyl-propionamide → (2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol (154920-05-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / tetrahydrofuran / 0 °C

2: Et₂BOMe, NaBH₄, HOAc, H₂O₂ / methanol

3: PPTS / benzene

4: Li, NH₃ / tetrahydrofuran / -60 °C

With sodium tetrahydroborate; diethyl methoxy borane; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; acetic acid; In tetrahydrofuran; methanol; benzene;

DOI:10.1016/S0040-4039(00)61344-8

upstream raw materials:

(4R,5S,6R)-4-Allyl-2,2,5-trimethyl-6-phenyl-[1,3]dioxane

(2R)-2-methyl-3-phenylpropanal

allylmagnesium bromide

benzyl bromide

Downstream raw materials:

(2R,3R)-6-Benzenesulfonyl-2-methyl-1-phenyl-hexan-3-ol

[(R)-4-Benzenesulfonyl-1-((R)-1-methyl-2-phenyl-ethyl)-butoxy]-tert-butyl-dimethyl-silane

(1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol

(1S,3R,4S,5R,6R,7S)-7-Benzyloxy-3,4-bis-benzyloxymethyl-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-5-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,6-diol