3-Oxatricyclo[3.2.1.02,4]octane

Base Information

• Chemical Name: 3-Oxatricyclo[3.2.1.02,4]octane
• CAS No.: 278-74-0
• Molecular Formula: C7H10 O
• Molecular Weight: 110.156
• Hs Code.: 2932999099
• European Community (EC) Number: 221-558-3,205-995-7
• NSC Number: 196237,103153
• DSSTox Substance ID: DTXSID10871884
• Nikkaji Number: J193.698K
• ChEMBL ID: CHEMBL3276054
• Mol file: 278-74-0.mol

Synonyms:278-74-0;3-Oxatricyclo[3.2.1.02,4]octane;2,3-EPOXYNORBORNANE;exo-2,3-Epoxynorbornane;3146-39-2;exo-Norbornene oxide;exo-2,3-Oxidonorbornane;Norbornane, 2,3-epoxy-, exo-;NSC 103153;Norbornane oxide, exo-2,3-;2,3-Epoxybicyclo(2.2.1)heptane;EINECS 205-995-7;EINECS 221-558-3;3-Oxatricyclo(3.2.1.02,4)octane;NSC 196237;Norbornane, 2,3-epoxy-, exo- (VAN);3-Oxatricyclo[3.2.1.0(2,4)]octane;exo-2,exo-3-Epoxybicyclo(2.2.1)heptane;exo-2,exo-3-Epoxybicyclo[2.2.1]heptane;3-Oxatricyclo(3.2.1.02,4)octane, exo-;Norbornane,3-epoxy-, exo-;norbornene oxide;2,3-Epoxybicyclo[2.2.1]heptane;3-Oxatricyclo(3.2.1.02,4)octane, (1alpha,2beta,4beta,5alpha)-;3-Oxatricyclo[3.2.1.02, exo-;3-Oxatricyclo(3.2.1.0(sup 2,4))octane, (1-alpha,2-beta,4-beta,5-alpha)-;3-Oxatricyclo[3.2.1.02, (1.alpha.,2.beta.,4.beta.,5.alpha.)-;3-Oxatricyclo(3.2.1.0(2,4)-)octane;SCHEMBL273290;CHEMBL3276054;3-oxatricyclo[3.2.1.0,octane;DTXSID10871884;MFCD00798067;NSC103153;NSC196237;3-oxatricyclo[3.2.1.0?,?]octane;AKOS015917736;NSC-103153;NSC-196237;3-oxatricyclo[3.2.1.0,2,4]octane;BS-43967;LS-97105;CS-0271515;E0779;FT-0691396;EN300-7501117;J-640019;J-800020;3-Oxatricyclo[3.2.1.0(2,4)]octane, (1.alpha.,2.beta.,4.beta.,5.alpha.)-

Chemical Property of 3-Oxatricyclo[3.2.1.02,4]octane

Chemical Property:

• Vapor Pressure: 1.98mmHg at 25°C
• Melting Point: 126 °C
• Boiling Point: 170.2°Cat760mmHg
• Flash Point: 10°C
• PSA: 12.53000
• Density: 1.159g/cm³
• LogP: 1.18370
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.073164938
• Heavy Atom Count: 8
• Complexity: 118

Purity/Quality:

98% ^*data from raw suppliers

2,3-Epoxynorbornane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC1C3C2O3

Technology Process of 3-Oxatricyclo[3.2.1.02,4]octane

There total 51 articles about 3-Oxatricyclo[3.2.1.02,4]octane 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: 98.0%

norborn-2-ene (498-66-8) + [(8,8,8',8'-tetramethylsalen)Cr(O)][CF3SO3] (98736-75-5) → 2,3-epoxynorbornane (278-74-0) + diaquo(8,8,8',8'-tetramethylsalen)chromium(III) triflate

Guidance literature:

With water; In acetonitrile; a dil. soln. of <0.02 M oxochromium(V) complex and norbornene (10-fold excess) in MeCN was stirred for 4 h, water was added; increased (6-fold)concn. of Cr-complex resulted in only 60% yield of norbornene oxide; rate const. at 23°C is given; soln. was evapd. to dryness in vacuo; Cr-complex was identified by IR spectrum; Kinetics;

DOI:10.1021/ja00311a064

Reference yield: 94.0%

norborn-2-ene (498-66-8) → 2,3-epoxynorbornane (278-74-0) + Norbornan-2-on (497-38-1) + Norborneol (497-36-9,497-37-0)

Guidance literature:

With (PF6)2; oxygen; In acetonitrile; at 65 ℃; under 2068.6 Torr; Mechanism; Product distribution; also in the presence of H₂O₂; other alkene; also hydroxylation of cyclohexane;

DOI:10.1021/ja00085a023

Reference yield: 90.0%

norborn-2-ene (498-66-8) + {Ru(2,2':6',2''-terpyridine)(N,N,N',N'-tetramethylethylenediamine)O}(ClO4)2*H2O → 2,3-epoxynorbornane (278-74-0) + {Ru(2,2':6',2''-terpyridine)(N,N,N',N'-tetramethylethylenediamine)(acetonitrile)}(2+) (127714-11-8)

Guidance literature:

With CH₃CN; In acetonitrile; Kinetics;

DOI:10.1039/DT9900000967

upstream raw materials:

peracetic acid

norborn-2-ene

chloroform

sodium acetate

Downstream raw materials:

Norbornan-2-on

2,3-dihydroxybicyclo[2.2.1]hept-5-an

(1R,4S)-Bicyclo[2.2.1]heptan-2-ol

hexahydro-4,7-methanobenzo[d][1,3]dioxol-2-one

Refernces

• 1、 Traylor, Teddy G.,Fann, Wen-Pang,Bandyopadhyay, Debkumar. "A Common Heterolytic Mechanism for Reactions of Iodosobenzenes, Peracids, Hydroperoxides, and Hydrogen Peroxide with Iron(III) Porphyrins". . p. 8009 - 8010. Retrieved 1989.
• 2、 Guo, Yingxiong,Xiao, Longqiang,Li, Pan,Zou, Wenhong,Zhang, Wenzhe,Hou, Linxi. "Binuclear molybdenum Schiff-base complex: An efficient catalyst for the epoxidation of alkenes". . . Retrieved 2019.
• 3、 Kojima, Takahiko,Matsuda, Yoshihisa. "Catalytic hydrocarbon oxygenation by a dinuclear ruthenium(II) complex with molecular oxygen". . p. 81 - 82. Retrieved 1999.
• 4、 Murakami, Tatsuya,Yamaguchi, Kazuya,Watanabe, Yoshihito,Morishima, Isao. "A New Active Intermediate in Monooxygenations Catalyzed by Iron Porphyrin Complexes". . p. 1343 - 1353. Retrieved 1998.
• 5、 Traylor, Teddy G.,Nakano, Taku,Dunlap, Beth E.,Traylor, Patricia S.,Dolphin, David. "Mechanisms of Hemin-Catalyzed Alkene Epoxidation. The Effect of Catalyst on the Regiochemistry of Epoxidation". . p. 2782 - 2784. Retrieved 1986.
• 6、 Ganeshpure, P. A.,Satish, S.. "Epoxidation of Alkenes with Iodosylbenzene catalysed by a Water-soluble Chromium(III) N,N'-Ethylene bis(salicylideneaminato) (salen) Complex using β-Cyclodextrin as a Phase Transfer Agent". . p. 981 - 982. Retrieved 1988.
• 7、 Roberts, Jeffery T.,Madix, Robert J.. "Epoxidation of Olefins on Silver: Conversion of Norbornene to Norbornene Oxide by Atomic Oxygen on Ag(110)". . p. 8540 - 8541. Retrieved 1988.
• 8、 Jacob, Mathew,Bhattacharya, Pabitra Krishna,Ganeshpure, Pralhad A.,Satish, Sheo,Sivaram, Swaminathan. "Epoxidation of Alkenes Catalyzed by Iron(III) Schiff Base Chelates. A Monooxygenase Model". . p. 1325 - 1327. Retrieved 1989.
• 9、 Tuel,Gontier,Teissier. "Zirconium containing mesoporous silicas: New catalysts for oxidation reactions in the liquid phase". . p. 651 - 652. Retrieved 1996.
• 10、 Chen,Kochi. "-". . p. 204. Retrieved 1977.