exo-2-Acetylbicyclo[2.2.1]hept-5-ene

Base Information

• Chemical Name: exo-2-Acetylbicyclo[2.2.1]hept-5-ene
• CAS No.: 824-61-3
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.194
• Mol file: 824-61-3.mol

Synonyms:Ethanone, 1-bicyclo[2.2.1]hept-5-en-2-yl-,exo-; Ketone, methyl5-norbornen-2-yl, exo- (8CI);exo-2-Acetylbicyclo[2.2.1]hept-5-ene; exo-5-Acetyl-2-norbornene

Chemical Property of exo-2-Acetylbicyclo[2.2.1]hept-5-ene

Chemical Property:

• Boiling Point: 191oC
• Flash Point: 62oC
• PSA: 17.07000
• Density: 1.049
• LogP: 1.78760

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of exo-2-Acetylbicyclo[2.2.1]hept-5-ene

There total 26 articles about exo-2-Acetylbicyclo[2.2.1]hept-5-ene 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: 100.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl vinyl ketone (78-94-4,25038-87-3) → bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (824-60-2,824-61-3,5063-03-6,65166-67-8,107740-92-1,128441-68-9,58001-95-9)

Guidance literature:

methyl vinyl ketone; With (S)-BINOL-Silica Hybrid (BSH); In dichloromethane; at 20 ℃; for 0.166667h;

cyclopenta-1,3-diene; In dichloromethane; at 20 ℃; for 2h; Temperature;

DOI:10.1007/s10562-018-2346-z

Reference yield: 95.06%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl vinyl ketone (78-94-4,25038-87-3) → 2-acetyl-5-norbornene (824-60-2) + exo-5-acetyl-2-norbornene (824-60-2,824-61-3,5063-03-6,58001-95-9,65166-67-8,107740-92-1,128441-68-9)

Guidance literature:

With [O=P(2-py)3W(CO)(NO)2](BF₄)2; In nitromethane; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2004.09.078

Reference yield: 89.0%

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + methyllithium (917-54-4) → bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (824-60-2,824-61-3,5063-03-6,65166-67-8,107740-92-1,128441-68-9,58001-95-9)

Guidance literature:

at 0 ℃; for 1h;

DOI:10.1016/0040-4039(88)85317-6

upstream raw materials:

cyclopenta-1,3-diene

methyl vinyl ketone

bi(cyclopentadiene)

endo-2-acetyl-5-norbornene

Downstream raw materials:

exo-5-acetyl-2-norbornene

(bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1, endo

(bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1, exo

(bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1

Refernces

• 1、 Belokon, Yuri N.,Dmitrienko, Artem O.,Gak, Alexander S.,Gerasimov, Igor S.,Kuznetsova, Svetlana A.,Larionov, Vladimir A.,Li, Han,Medvedev, Michael G.,Nelyubina, Yulia V.,North, Michael,Saghyan, Ashot S.,Smol'yakov, Alexander F.,Zhereb, Vladimir P.. "The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Br?nsted acid catalysts". supporting information. p. 1124 - 1134. Retrieved 2020/07/10.
• 2、 Leber, Phyllis,Kidder, Katherine,Viray, Don,Dietrich-Peterson, Eric,Fang, Yuan,Davis, Alexander. "Stereoselectivity in a series of 7-alkylbicyclo[3.2.0]hept-2-enes: Experimental and computational perspectives". . . Retrieved 2018/08/03.