Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)-

Base Information

• Chemical Name: Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)-
• CAS No.: 272776-88-2
• Molecular Formula: C14H16O3
• Molecular Weight: 232.279
• DSSTox Substance ID: DTXSID20457638
• Nikkaji Number: J1.928.112D
• Wikidata: Q82280553
• Mol file: 272776-88-2.mol

Synonyms:272776-88-2;Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)-;DTXSID20457638;(S)-2beta-[4-(4-Methoxybenzyloxy)-2-butynyl]oxirane

Chemical Property of Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)-

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 232.109944368
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)COCC#CCC2CO2
• Isomeric SMILES: COC1=CC=C(C=C1)COCC#CC[C@H]2CO2

Technology Process of Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)-

There total 4 articles about Oxirane, [4-[(4-methoxyphenyl)methoxy]-2-butynyl]-, (2S)- 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: 42.5%

2-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-oxirane (577749-28-1) → 1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne (272776-88-2) + (R)-6-(4-Methoxy-benzyloxy)-hex-4-yne-1,2-diol

Guidance literature:

With (S,S)-salen-Co(III)OAc; water; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo026892y

Reference yield:

(S)-1-Chloro-6-(4-methoxy-benzyloxy)-hex-4-yn-2-ol → 1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne (272776-88-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -10 ℃; for 1h;

DOI:10.1016/S0039-128X(00)00087-8

Reference yield:

3-(4-methoxybenzyloxy)propyne (4039-83-2) → 1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne (272776-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / BuLi; BF₃*Et₂O

2: 90 percent / K₂CO₃ / acetonitrile

3: 42.5 percent / (S,S)-salen-Co(III)OAc; H₂O / tetrahydrofuran / 12 h / 20 °C

With n-butyllithium; (S,S)-salen-Co(III)OAc; boron trifluoride diethyl etherate; water; potassium carbonate; In tetrahydrofuran; acetonitrile; 1: Yamaguchi reaction;

DOI:10.1021/jo026892y

upstream raw materials:

2-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-oxirane

3-(4-methoxybenzyloxy)propyne

Downstream raw materials:

(5R)-1-(4-methoxybenzyl)oxynona-8-en-2-yn-5-ol

5-(4-methoxybenzyloxy)-1-phenylsulfanylmethyl-(1S)-3-pentynyl alcohol

6-phenylsulfanyl-(E,2S)-2-hexene-1,5-diol

6-phenylsulfanyl-(5S)-2-hexyne-1,5-diol