1,4-Butanediol, 1,4-diphenyl-, (1R,4R)-

Base Information

• Chemical Name: 1,4-Butanediol, 1,4-diphenyl-, (1R,4R)-
• CAS No.: 214280-56-5
• Molecular Formula: C16H18O2
• Molecular Weight: 242.318
• DSSTox Substance ID: DTXSID40443154
• Wikidata: Q82260866
• Mol file: 214280-56-5.mol

Synonyms:214280-56-5;Rel-(1R,4R)-1,4-diphenylbutane-1,4-diol;(1R,4R)-1,4-DIPHENYLBUTANE-1,4-DIOL;13401-43-9;1,4-Butanediol, 1,4-diphenyl-, (1R,4R)-;DTXSID40443154

Chemical Property of 1,4-Butanediol, 1,4-diphenyl-, (1R,4R)-

Chemical Property:

• PSA: 40.46000
• LogP: 3.23380
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 242.130679813
• Heavy Atom Count: 18
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CCC(C2=CC=CC=C2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CC[C@H](C2=CC=CC=C2)O)O

Technology Process of 1,4-Butanediol, 1,4-diphenyl-, (1R,4R)-

There total 9 articles about 1,4-Butanediol, 1,4-diphenyl-, (1R,4R)- 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: 99.0%

phenacylacetophenone (495-71-6) → (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol (214280-56-5)

Guidance literature:

With dimethylsulfide borane complex; C₁₇H₁₉NO*C₃H₉BO₃; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2015.01.140

Reference yield:

phenacylacetophenone (495-71-6) → (1R,4S)-1,4-diphenylbutane-1,4-diol (13401-42-8) + (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol (214280-56-5)

Guidance literature:

With sodium tetrahydroborate; (1R,2R)-β-ketoiminato cobalt(II); In ethanol; chloroform; at -40 ℃; for 72h; Title compound not separated from byproducts;

Reference yield:

(R)-1-phenylprop-2-en-1-ol (104713-12-4) → (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol (214280-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2: 93 percent / Grubbs' catalyst / CH₂Cl₂ / 42 h / Heating

3: H₂ / Raney Ni

4: tetra-N-butylammonium fluoride / tetrahydrofuran

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; hydrogen; Grubbs catalyst first generation; nickel; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Cyclization / 3: Reduction / 4: desilylation;

DOI:10.1021/jo9811524

upstream raw materials:

phenacylacetophenone

(R)-1-phenylprop-2-en-1-ol

(4R,7R)-2,2,4,7-Tetraphenyl-4,7-dihydro-[1,3,2]dioxasilepine

Diphenyl-bis-((R)-1-phenyl-allyloxy)-silane

Downstream raw materials:

(1R,4R)-1,4-bis(methanesulfonyloxy)-1,4-diphenylbutane

(2S,5S)-1-amino-2,5-diphenylpyrrolidine

(2S,5S)-2,5-diphenyl-1-(3,5-dimethylphenyl)phospholane

(2S,5S)-(-)-1-(3,5-dimethylphenyl)-1-oxo-2,5-diphenylphospholane