Tricyclo[3.1.1.1(3,7)]octan-2-one

Base Information

• Chemical Name: Tricyclo[3.1.1.1(3,7)]octan-2-one
• CAS No.: 6239-87-8
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.167
• NSC Number: 122679
• DSSTox Substance ID: DTXSID40298363
• Mol file: 6239-87-8.mol

Synonyms:Tricyclo[3.1.1.1(3,7)]octan-2-one;6239-87-8;NSC122679;DTXSID40298363;NSC-122679

Chemical Property of Tricyclo[3.1.1.1(3,7)]octan-2-one

Chemical Property:

• Vapor Pressure: 0.145mmHg at 25°C
• Boiling Point: 215.8°Cat760mmHg
• Flash Point: 77.2°C
• Density: 1.215g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3C2CC1C3=O

Technology Process of Tricyclo[3.1.1.1(3,7)]octan-2-one

There total 5 articles about Tricyclo[3.1.1.1(3,7)]octan-2-one 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:

(1R,2R,4S,5S,6R)-6-Chloromethyl-3-oxa-tricyclo[3.2.1.02,4]octane → Tricyclo<3.2.1.03.6>octanon-2 (6239-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Li, BF₃*Et₂O / tetrahydrofuran

2: K₂Cr₂O₇, aq. H₂SO₄

With potassium dichromate; sulfuric acid; boron trifluoride diethyl etherate; lithium; In tetrahydrofuran;

DOI:10.1021/ja00962a032

Reference yield:

exo-Tricyclo<3.2.1.03.6>octanol-2 (6239-89-0,6239-90-3,87507-42-4,87507-44-6,87507-45-7,87507-60-6,87507-61-7,90528-09-9) → Tricyclo<3.2.1.03.6>octanon-2 (6239-87-8)

Guidance literature:

With potassium dichromate; sulfuric acid;

DOI:10.1021/ja00962a032

Reference yield:

5-(Bromomethyl)bicyclo<2.2.1>hept-2-ene (17016-12-5) → Tricyclo<3.2.1.03.6>octan-2-one (6239-87-8)

Guidance literature:

Multistep reaction; (i) NaBH₄, ZnCl₂, BF₃-Et₂O, (ii) Na₂Cr₂O₇, aq. H₂SO₄, (iii) NaNH₂, liq. NH₃, Et₂O;

DOI:10.1016/S0040-4020(01)83272-5

upstream raw materials:

exo-Tricyclo<3.2.1.0^3.6>octanol-2

5-(Bromomethyl)bicyclo<2.2.1>hept-2-ene

Downstream raw materials:

exo-2-phenyl-endo-2-tricyclo<3.2.1.0^3.6>octanol

endo-2-phenyltricyclo<3.2.1.0^3.6>octane

(1R,2S,3S,5R,6S)-2-Chloro-2-phenyl-tricyclo[3.2.1.0^3,6]octane

endo-2-phenyl-exo-2-tricyclo<3.2.1.0^3.6>octanol