(1R)-1-phenylbut-3-en-1-ol

Base Information

• Chemical Name: (1R)-1-phenylbut-3-en-1-ol
• CAS No.: 85551-57-1
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.205
• UNII: D8XKK42TJ4
• Nikkaji Number: J502.545A
• Mol file: 85551-57-1.mol

Synonyms:(1R)-1-phenylbut-3-en-1-ol;(R)-1-phenyl-3-buten-1-ol;85551-57-1;D8XKK42TJ4;SCHEMBL5732595;(R)-1-phenylbut-3-en-1-ol;(1R)-1-phenyl-3-buten-1-ol;(R)-1-phenyl-3-buten-1 -ol;RGKVZBXSJFAZRE-SNVBAGLBSA-N;1-Phenylbut-3-en-1-ol, (1R)-;(R)-(+)-1-Phenyl-3-buten-1-ol;(alphaR)-alpha-(2-Propenyl)benzenemethanol;Benzenemethanol, alpha-2-propenyl-, (R)-;(alphaR)-alpha-2-Propen-1-ylbenzenemethanol;(+)-(alphaR)-alpha-2-Propenylbenzenemethanol;Benzenemethanol, alpha-2-propenyl-, (alphaR)-;A844667;Benzenemethanol, alpha-2-propen-1-yl-, (alphaR)-

Chemical Property of (1R)-1-phenylbut-3-en-1-ol

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of (1R)-1-phenylbut-3-en-1-ol

There total 103 articles about (1R)-1-phenylbut-3-en-1-ol 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%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + benzaldehyde (100-52-7) → (R)-1-Phenylbut-3-en-1-ol (85551-57-1,936-58-3)

Guidance literature:

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; In toluene; at -30 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja104956s

Reference yield: 98.0%

(+)-(R)-1-phenylbut-3-en-1-yl acetate (181227-42-9) → (R)-1-Phenylbut-3-en-1-ol (85551-57-1,936-58-3)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 2h;

DOI:10.1002/chem.201301980

Reference yield: 90.0%

allyltrimethoxysilane (2551-83-9) + benzaldehyde (100-52-7) → (R)-1-Phenylbut-3-en-1-ol (85551-57-1,936-58-3)

Guidance literature:

With silver fluoride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In d⁽⁴⁾-methanol; at -24.16 ℃; Temperature;

DOI:10.1021/jo400451u

upstream raw materials:

furfural

allyltrichlorosilane

1-phenylbut-3-en-1-one

benzaldehyde

Downstream raw materials:

(1R)-carbonic acid tert-butyl ester 1-phenylbut-3-enyl ester

1-(2-{[(R)-1-phenylbut-3-enyloxy]methyl}allyl)benzene

(+)-(R)-δ-(phenyl)-δ-valerolactone

C₁₆H₂₆OSi

Refernces

• 1、 Hurem, David,Moiseev, Andrey G.,Simionescu, Razvan,Dudding, Travis. "A detailed NMR- and DFT-based study of the Sakurai-Hosomi-Yamamoto asymmetric allylation reaction". . p. 4440 - 4445. Retrieved 2013.
• 2、 ?eimyt?, Simona,Ston?ius, Sigitas. "Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions". supporting information. . Retrieved 2020/12/21.
• 3、 Chen, Chinpiao,Kumbhar, Sharad V.. "A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes". . . Retrieved 2020/09/22.