1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)-

Base Information

• Chemical Name: 1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)-
• CAS No.: 675127-22-7
• Molecular Formula: C18H28O2
• Molecular Weight: 276.419
• DSSTox Substance ID: DTXSID60459550
• Nikkaji Number: J2.001.155F
• Wikidata: Q82283343
• Mol file: 675127-22-7.mol

Synonyms:1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)-;675127-22-7;DTXSID60459550;(4S,5S)-5-(Benzyloxy)-1-undecene-4-ol

Chemical Property of 1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)-

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 276.208930132
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(C(CC=C)O)OCC1=CC=CC=C1
• Isomeric SMILES: CCCCCC[C@@H]([C@H](CC=C)O)OCC1=CC=CC=C1

Technology Process of 1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)-

There total 11 articles about 1-Undecen-4-ol, 5-(phenylmethoxy)-, (4S,5S)- 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: 90.0%

(+)-pinanediol (1S,1'S)-1-(1'-benzyloxy)heptylbut-3-eneboronate (675127-21-6) → 1-[1-benzyloxy-(1S)-heptyl]-(1S)-3-butenyl alcohol (675127-22-7)

Guidance literature:

(+)-pinanediol (1S,1'S)-1-(1'-benzyloxy)heptylbut-3-eneboronate; With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.166667h;

With dihydrogen peroxide; In tetrahydrofuran; at 0 - 45 ℃; for 1.75h; Further stages.;

DOI:10.1039/b308709c

Reference yield: 88.0%

1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane (900783-34-8) + vinyl magnesium bromide (1826-67-1) → 1-[1-benzyloxy-(1S)-heptyl]-(1S)-3-butenyl alcohol (675127-22-7)

Guidance literature:

vinyl magnesium bromide; With copper(l) cyanide; In tetrahydrofuran; at -78 ℃; for 0.25h;

1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane; In tetrahydrofuran; at -78 - 20 ℃;

With ammonium chloride; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.tet.2011.03.102

Reference yield: 57.0%

1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane (900783-34-8) + Vinyl bromide (593-60-2,25951-54-6) → 1-[1-benzyloxy-(1S)-heptyl]-(1S)-3-butenyl alcohol (675127-22-7)

Guidance literature:

Vinyl bromide; With magnesium; In tetrahydrofuran; for 0.5h;

1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane; With copper(I) bromide; In tetrahydrofuran; at -30 ℃;

DOI:10.1016/j.tetasy.2006.03.024

upstream raw materials:

(+)-pinanediol (1S,1'S)-1-(1'-benzyloxy)heptylbut-3-eneboronate

1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane

Vinyl bromide

allyltributylstanane

Downstream raw materials:

(5R,6R,7E,10S)-10-[(1'S)-1'-benzyloxyheptyl]-5,6-isopropylidenedioxy-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

(5R,6R,7E,10S)-10-[(1'S)-1'-benzyloxyheptyl]-5,6-dibenzyloxy-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

1-[1-benzyloxy-(1S)-heptyl]-(1S)-3-butenyl 3-[2,2-dimethyl-5-vinyl-(4R,5R)-1,3-dioxolan-4-yl]propanoate

(4R,5R)-4,5-dibenzyloxyhept-6-enoic acid (1'S,1''S)-1'-(1''-benzyloxyheptyl)-3'-butenyl ester