1-(1-Adamantyl)ethanol

Base Information

• Chemical Name: 1-(1-Adamantyl)ethanol
• CAS No.: 26750-08-3
• Molecular Formula: C₁₂H₂₀O
• Molecular Weight: 180.29
• Hs Code.: 2906199090
• DSSTox Substance ID: DTXSID00377845
• Nikkaji Number: J522.871I,J3.639.054I
• Mol file: 26750-08-3.mol

Synonyms:1-(1-adamantyl)ethanol;26750-08-3;1-(Adamantan-1-yl)ethanol;1-Adamantan-1-yl-ethanol;1-(1-hydroxyethyl)adamantane;1-(ADAMANTAN-1-YL)ETHAN-1-OL;adamantylethanol;1-adamantylethanol;adamantan-1-ylethanol;Enamine_003722;1-Adamantylmethylmethanol;a-Methyl-1-adamantanemethanol;SCHEMBL182779;alpha-methyl-1-adamantanemethanol;DTXSID00377845;YALBLVPSPRKDJI-UHFFFAOYSA-N;HMS1404J04;BBA75008;MFCD01321095;AKOS000125794;AKOS006343066;AKOS016050322;AS-9445;SB84275;IDI1_007365;EU-0066811;FT-0607297;FT-0724638;J3.639.054I;VU0118695-2;1-[(3R,5S,7s)-adamantan-1-yl]ethan-1-ol;EN300-136593;EN300-236081;SR-01000389376;SR-01000389376-1;Z56757712;F0035-0008;1-[1,3,5-(Methylidynetrismethylene)cyclohexane-1-yl]ethanol

Chemical Property of 1-(1-Adamantyl)ethanol

Chemical Property:

• PSA: 20.23000
• LogP: 2.58360
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 180.151415257
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

98%Min ^*data from raw suppliers

1-(1-Adamantyl)ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C12CC3CC(C1)CC(C3)C2)O
• Uses: 1-(1-Adamantyl)ethanol is patented for use to catalyze the change of the load state of MHC molecules and possible use in treatment and diagnosis of cancer, infectious diseases, and autoimmune diseases. It also shows inhibitory action against herpes simplex virus type 1, vaccinia virus, vesicular stomatitis virus, fowl plaque virus, respiratory syncytial virus, and Venezuelan encephalitis virus.

Technology Process of 1-(1-Adamantyl)ethanol

There total 7 articles about 1-(1-Adamantyl)ethanol 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:

→ 1-adamantylethanol (91410-69-4,138309-12-3,138381-75-6,26750-08-3) + 1-acetyladamantane (1660-04-4)

Guidance literature:

Reference yield:

1-acetyladamantane (1660-04-4) + benzonitrile (100-47-0) → 1-adamantylethanol (91410-69-4,138309-12-3,138381-75-6,26750-08-3) + rimantadine (13392-28-4,117857-51-9,117857-52-0,129277-01-6) + (1-adamantan-1-yl-ethyl)-benzyl-amine (88313-74-0)

Guidance literature:

With hydrogen; Cu + 6percent LiOH on aluminum γ-oxide; at 260 ℃; under 15200 Torr; Yield given. Further byproducts given. Yields of byproduct given; flow-through setup;

Reference yield:

1-adamantylethanol (91410-69-4,138309-12-3,138381-75-6,26750-08-3) + (3,5-dimethylphenyl)dimethylsilane → (1-(adamantan-1-yl)ethoxy)(3,5-dimethylphenyl)dimethylsilane + (1-(adamantan-1-yl)ethoxy)(3,5-dimethylphenyl)dimethylsilane + (R)-1-(adamantyl)ethanol (26750-08-3,138309-12-3,138381-75-6,91410-69-4) + (S)-1-(1-adamantan-1-yl)ethanol (138309-12-3)

Guidance literature:

(3,5-dimethylphenyl)dimethylsilane; With copper(l) chloride; sodium t-butanolate; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; In toluene; at 20 ℃; for 0.166667h; Glovebox; Inert atmosphere;

1-adamantylethanol; In toluene; at 20 ℃; for 12h; enantioselective reaction; Glovebox; Inert atmosphere; Resolution of racemate;

DOI:10.1021/acs.orglett.0c03943

upstream raw materials:

propyl cyanide

1-acetyladamantane

benzonitrile

acetonitrile

Downstream raw materials:

(R)-1-(adamantyl)ethanol

(S)-1-(1-adamantan-1-yl)ethanol

3-nitroxyadamantane-1-carboxylic acid

1-acetyladamantane

Refernces

• 1、 -. "Methods of acylating adamantane, tricyclo[5.2.1.02,6], and decalin compounds". . . Retrieved 2008/06/13.
• 2、 Kozlov, N. G.,Vyalimyae, T. K.. "REDUCTIVE AMINATION OF 1-ACETYLADAMANTANE". . p. 539 - 542. Retrieved 2007/10/02.