bicyclo[3.3.1]non-3-ene

Base Information

• Chemical Name: bicyclo[3.3.1]non-3-ene
• CAS No.: 6671-66-5
• Molecular Formula: C9H14
• Molecular Weight: 122.21
• Hs Code.: 2902199090
• Mol file: 6671-66-5.mol

Synonyms:bicyclo[3.3.1]non-3-ene

Chemical Property of bicyclo[3.3.1]non-3-ene

Chemical Property:

• Vapor Pressure: 2.59mmHg at 25°C
• Boiling Point: 164.4°C at 760 mmHg
• Flash Point: 37.8°C
• PSA: 0.00000
• Density: 0.912g/cm³
• LogP: 2.75270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bicyclo[3.3.1]non-3-ene

There total 36 articles about bicyclo[3.3.1]non-3-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: 21.0%

methanol (67-56-1) + 2-bicyclo[3.2.2]nonyl p-toluenesulfonate → bicyclo[3.3.1]non-2-ene (6671-66-5) + tricyclo[3.3.1.02,8]nonane (331-65-7) + 2-bicyclo[3.2.2]nonene (40319-81-1) + exo-2-Methoxybicyclo<3.3.1>nonan (120263-64-1)

Guidance literature:

With 2,6-dimethylpyridine; at 50 ℃; Further Variations:; Temperatures; Product distribution; Kinetics; Thermodynamic data;

DOI:10.1021/jo9914061

Reference yield: 10.0%

2,2,2-trifluoroethanol (75-89-8) + 2-bicyclo[3.2.2]nonyl p-toluenesulfonate → bicyclo[3.3.1]non-2-ene (6671-66-5) + 2-bicyclo[3.2.2]nonene (40319-81-1) + 2-(2,2,2-trifluoroethoxy)bicyclo[3.2.2]nonane + exo-2-(2,2,2-trifluoroethoxy)bicyclo[3.3.31]nonane

Guidance literature:

With 2,6-dimethylpyridine; at 40 ℃; Further Variations:; Temperatures; Product distribution; Kinetics; Thermodynamic data;

DOI:10.1021/jo9914061

Reference yield:

3-(3,3-Diaethoxycarbonyl-cyclohexen-1-yl-1)-propen-2-saeureaethylester (26775-58-6) → bicyclo[3.3.1]non-2-ene (6671-66-5)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂ / PtO₂ / ethanol

2: NaH / 1,2-dimethoxy-ethane

3: aq. KOH / methanol

4: H₂SO₄ / 1,2-dichloro-ethane

5: Al(OiPr)3

6: aq. KOH / ethanol

7: diethyl ether

8: Py

9: aq. KOH, Py / ethanol

10: KOtBu / dimethylsulfoxide

11: MeLi / diethyl ether

With pyridine; potassium hydroxide; sulfuric acid; potassium tert-butylate; methyllithium; hydrogen; aluminum isopropoxide; sodium hydride; platinum(IV) oxide; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.1021/ja00707a034

upstream raw materials:

2-morpholinobicyclo<3.3.1>nonane

bicyclo[3.3.1]non-1-ene

Bicyclo[3.3.1]non-2-en-9-one

Thiocarbonic acid O-bicyclo[3.3.1]non-1-yl ester O-p-tolyl ester

Downstream raw materials:

bicyclo[3.3.1]nonan-3-one

bicyclo<3.3.1>nonan-3α-ol

bicyclo<3.3.1>nonan-3β-ol

endo-Bicyclo<3.3.1>nonan-2-ol

Refernces

• 1、 Okazaki, Takao,Terakawa, Eiichi,Kitagawa, Toshikazu,Takeuchi, Ken'ichi. "Solvolysis of 2-bicyclo[3.2.2]nonyl p-toluenesulfonate. Evidence for the formation of classical carbocation intermediates". . p. 1680 - 1684. Retrieved 2007/10/03.
• 2、 Grob, Cyril A.,Waldner, Adrian. "BRIDGING STRAIN IN THE SOLVOLYSIS OF EPIMERIC BICYCLIC TOLUENESULFONATES". . p. 3235 - 3238. Retrieved 2007/10/02.