Cyclooct-4-enol

Base Information

• Chemical Name: Cyclooct-4-enol
• CAS No.: 4277-34-3
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 2906199090
• European Community (EC) Number: 224-280-0,804-384-8
• NSC Number: 119487
• DSSTox Substance ID: DTXSID701316411
• Nikkaji Number: J3.040.374F,J80.788E
• Mol file: 4277-34-3.mol

Synonyms:Cyclooct-4-enol;4277-34-3;Cyclooct-4-en-1-ol;4-cycloocten-1-ol;5-hydroxy-1-cyclooctene;(4Z)-cyclooct-4-en-1-ol;(Z)-Cyclooct-4-enol;(E)-cyclooct-4-enol;5-hydroxycyclooctene;rel-(1R,4E,pR)-Cyclooct-4-enol;85081-69-2;(Z)-cyclooct-4-en-1-ol;EINECS 224-280-0;(R)-TCO-OH;4-Cyclooctenol;39637-78-0;NSC119487;1-Hydroxy-4-cyclooctene;(E)-4-Cyclooctene-1-ol;(4E)-cyclooct-4-en-1-ol;SCHEMBL560703;SCHEMBL868155;(4E)-CO-OH;UCPDHOTYYDHPEN-UPHRSURJSA-N;DTXSID701316411;rel-(1R,4E,pS)-Cyclooct-4-enol;MFCD06252442;AKOS006292831;CS-W006126;NSC 119487;NSC-119487;AS-19720;BP-31072;EN300-316153;H10619;EN300-1177815;A872822;J-640359;J-800364;W-202740

Chemical Property of Cyclooct-4-enol

Chemical Property:

• Vapor Pressure: 0.0724mmHg at 25°C
• Boiling Point: 202.2°Cat760mmHg
• PKA: 15.13±0.20(Predicted)
• Flash Point: 75.6°C
• PSA: 20.23000
• Density: 0.954g/cm³
• LogP: 1.86760
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 96.7

Purity/Quality:

99.9% ^*data from raw suppliers

5-Hydroxy-1-cyclooctene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC=CCCC(C1)O
• Isomeric SMILES: C1C/C=C\CCC(C1)O

Technology Process of Cyclooct-4-enol

There total 29 articles about Cyclooct-4-enol 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: 96.1%

(Z)-9-oxabicyclo[6.1.0]non-4-ene (19740-90-0,57378-34-4,65207-47-8,73176-71-3,73176-86-0,117468-08-3,637-90-1) → (Z)-cyclooct-4-enol (4277-34-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 4h;

Reference yield: 77.0%

(Z)-cyclooct-4-enol (4277-34-3) → rel-(1R-4E-pR)-cyclooct-4-enol (4277-34-3,31598-74-0,39637-78-0,39637-79-1,39638-01-2,85081-69-2)

Guidance literature:

With benzoic acid methyl ester; for 12h; Irradiation;

DOI:10.1002/anie.201915079

Reference yield: 58.0%

4-cycloocten-1-yl acetate (31598-73-9) → (Z)-cyclooct-4-enol (4277-34-3)

Guidance literature:

With potassium hydroxide; In water; for 5h; Heating;

DOI:10.1039/P19900002951

upstream raw materials:

1,5-cis,cis-cyclooctadiene

(Z)-9-oxabicyclo[6.1.0]non-4-ene

4-cycloocten-1-yl acetate

cis-1,4-dihydroxycyclooctane

Downstream raw materials:

2-(Phenylseleno)-9-oxabicyclo<4.2.1>nonane

2-(Phenylseleno)-9-oxabicyclo<3.3.1>nonane

cyclooctanol

rel-(1R-4E-pR)-cyclooct-4-enol

Refernces

• 1、 Pigga, Jessica E.,Rosenberger, Julia E.,Jemas, Andrew,Boyd, Samantha J.,Dmitrenko, Olga,Xie, Yixin,Fox, Joseph M.. "General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties**". supporting information. p. 14975 - 14980. Retrieved 2021/05/31.
• 2、 Béquignat, Jean-Baptiste,Boucheix, Claude,Canitrot, Damien,Chezal, Jean-Michel,Degoul, Fran?oise,Miot-Noirault, Elisabeth,Moreau, Emmanuel,Navarro-Teulon, Isabelle,Quintana, Mercedes,Rondon, Aurélie,Taiariol, Ludivine,Ty, Nancy. "Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction". supporting information. . Retrieved 2020/07/21.