13,14-dioxatricyclo[8.2.1.1~4,7~]tetradeca-1(12),4,6,10-tetraene

Base Information

• Chemical Name: 13,14-dioxatricyclo[8.2.1.1~4,7~]tetradeca-1(12),4,6,10-tetraene
• CAS No.: 5088-46-0
• Molecular Formula: C12H12O2
• Molecular Weight: 188.2225
• Mol file: 5088-46-0.mol

Synonyms:

Chemical Property of 13,14-dioxatricyclo[8.2.1.1~4,7~]tetradeca-1(12),4,6,10-tetraene

Chemical Property:

• Vapor Pressure: 0.0147mmHg at 25°C
• Boiling Point: 265.8°Cat760mmHg
• Flash Point: 115.2°C
• Density: 1.126g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 13,14-dioxatricyclo[8.2.1.1~4,7~]tetradeca-1(12),4,6,10-tetraene

There total 10 articles about 13,14-dioxatricyclo[8.2.1.1~4,7~]tetradeca-1(12),4,6,10-tetraene 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: 73.0%

<5-<(trimethylsilyl)methyl>furfuryl>trimethylammonium iodide (76233-24-4) → [2.2](2.5)furanocyclophane (5088-46-0,73650-68-7)

Guidance literature:

With tetrabutyl ammonium fluoride; at 110 ℃; for 4h; sealed tube;

DOI:10.1021/jo00318a047

Reference yield: 71.0%

N,N,N-trimethyl-1-(5-methylfuran-2-yl)methanammonium hydroxide → [2.2](2.5)furanocyclophane (5088-46-0,73650-68-7)

Guidance literature:

at 150 - 155 ℃; for 3h; under 0.2 Torr; Pyrolysis;

DOI:10.1055/s-0040-1707372

Reference yield:

2-methylfuran (534-22-5) → [2.2](2.5)furanocyclophane (5088-46-0,73650-68-7)

Guidance literature:

Multi-step reaction with 4 steps

1: water / Reflux; Inert atmosphere

2: diethyl ether / 2 h / 0 °C / Inert atmosphere

3: silver(l) oxide / water / Inert atmosphere

4: 3 h / 150 - 155 °C / 0.2 Torr / Pyrolysis

With silver(l) oxide; In diethyl ether; water; 1: |Mannich Aminomethylation / 4: |Hofmann Elimination;

DOI:10.1055/s-0040-1707372

upstream raw materials:

methylfurmethide

(3,4-Dimethyl-benzyl)-trimethyl-ammonium; iodide

<5-<(trimethylsilyl)methyl>furfuryl>trimethylammonium iodide

2,5-dimethylene-2,5-dihydro-furan

Refernces

• 1、 Fletcher,Sutherland. "-". . p. 1504. Retrieved 1969.
• 2、 Wong,Paudler. "". . p. 2570. Retrieved 1974.
• 3、 Trahanovsky, Walter S.,Miller, Deborah Louise,Wang, Yili. "Oligomerization of the Thiophene-Based p-Quinodimethanes 2,5-dihydrothiophene and 2-Ethylidene-5-methylene-2,5-dihydrothiophene". . p. 8980 - 8986. Retrieved 2007/10/03.
• 4、 Ito, Yoshihiko,Miyata, Satoru,Nakatsuka, Masashi,Saegusa, Takeo. "Fluoride-Induced 1,6-Elimination to p-Quinodimethane. A New Preparative Method for Paracyclophane, (2.5)Furanophane and (2.5)Thiophenophane". . p. 1043 - 1044. Retrieved 2007/10/02.