1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile

Base Information

• Chemical Name: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile
• CAS No.: 264279-20-1
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.235
• Mol file: 264279-20-1.mol

Synonyms:2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile

Chemical Property of 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile

Chemical Property:

• Boiling Point: 249.2±23.0 °C(Predicted)
• Density: 1.04±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, Diethyl Ether, Ethyl Acetate

Purity/Quality:

1,3,3-Trimethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile is used in the synthesis of Retinoic acid derivatives.

Technology Process of 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile

There total 5 articles about 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile 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: 95.0%

2,6,6-trimethyl-2-cyclohexenecarbonitrile (57524-13-7) → 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile (264279-20-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 - 20 ℃;

DOI:10.1002/(SICI)1099-0690(200003)2000:5<829::AID-EJOC829>3.0.CO;2-Z

Reference yield:

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) → 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile (264279-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0 - 20 °C

1.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C

2.1: 86 percent / conc. H₂SO₄ / nitromethane / 0.5 h / 0 °C

3.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C

With sulfuric acid; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; nitromethane; ethyl acetate; 1.1: Metallation / 1.2: Condensation / 2.1: Cyclization / 3.1: Epoxidation;

DOI:10.1002/(SICI)1099-0690(200003)2000:5<829::AID-EJOC829>3.0.CO;2-Z

Reference yield:

geranonitrile (5146-66-7,80748-12-5) → 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile (264279-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / conc. H₂SO₄ / nitromethane / 0.5 h / 0 °C

2: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C

With sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In nitromethane; ethyl acetate; 1: Cyclization / 2: Epoxidation;

DOI:10.1002/(SICI)1099-0690(200003)2000:5<829::AID-EJOC829>3.0.CO;2-Z

upstream raw materials:

2,6,6-trimethyl-2-cyclohexenecarbonitrile

6-Methyl-hept-5-en-2-on

geranonitrile

5-methyl-4-hexenenitrile

Downstream raw materials:

(3RS,all-E)-hydroxyretinal

C₂₀H₂₈O₂

Refernces

• 1、 Zhang, Jianye,Dong, Zhiqian,Mundla, Sreenivasa Reddy,Hu, X. Eric,Seibel, William,Papoian, Ruben,Palczewski, Krzysztof,Golczak, Marcin. "Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration". supporting information. p. 477 - 491. Retrieved 2015/01/30.
• 2、 Jansen, Frans Jos H. M.,Lugtenburg, Johan. "Synthesis and characterization of all-E-(4,4'-13C2)-astaxanthin strategies for labelling the C15-end groups of carotenoids". . p. 829 - 836. Retrieved 2007/10/03.