6-Bromo-1,4-dioxaspiro[4.4]non-6-ene

Base Information

• Chemical Name: 6-Bromo-1,4-dioxaspiro[4.4]non-6-ene
• CAS No.: 68241-78-1
• Molecular Formula: C7H9BrO2
• Molecular Weight: 205.051
• DSSTox Substance ID: DTXSID80451278
• Nikkaji Number: J1.767.988K
• Wikidata: Q82271225
• Mol file: 68241-78-1.mol

Synonyms:68241-78-1;6-bromo-1,4-dioxaspiro[4.4]non-6-ene;2-BROMO-2-CYCLOPENTEN-1-ONEETHYLENEKETAL;2-Bromo-2-cyclopenten-1-one ethyleneketal;SCHEMBL17449347;DTXSID80451278;1-bromo-6,9-dioxaspiro[4.4]non-1-ene;6-Bromo-1,4-dioxaspiro[4.4]nonane-6-ene

Chemical Property of 6-Bromo-1,4-dioxaspiro[4.4]non-6-ene

Chemical Property:

• PSA: 18.46000
• LogP: 1.80210
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 203.97859
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2(C(=C1)Br)OCCO2

Technology Process of 6-Bromo-1,4-dioxaspiro[4.4]non-6-ene

There total 7 articles about 6-Bromo-1,4-dioxaspiro[4.4]non-6-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: 85.0%

2-bromo-2-cyclopenten-1-one (10481-34-2) + ethylene glycol (107-21-1) → 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 43h; Heating; azeotropic removal of water;

DOI:10.1021/jo00349a009

Reference yield: 60.0%

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + 2-bromo-2-cyclopenten-1-one (10481-34-2) → 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1)

Guidance literature:

With Nafion-TMS; In chloroform; for 10h; Heating;

DOI:10.1002/1615-4169(200201)344:1<57::AID-ADSC57>3.0.CO;2-0

Reference yield:

cyclopent-2-enone (930-30-3) → 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Br₂; Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 67 percent / p-toluenesulfonic acid / benzene / 18 h / Heating

With bromine; toluene-4-sulfonic acid; triethylamine; In dichloromethane; benzene;

DOI:10.1021/ol0615230

upstream raw materials:

cyclopent-2-enone

ethylene glycol

2-bromo-2-cyclopenten-1-one

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

Downstream raw materials:

2-benzyloxymethyl-3-(2-hydroxy-1-methyl-ethyl)-cyclopentanol

5-benzyloxymethyl-4-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopent-2-enone

2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopentanone

2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopentanol

Refernces

• 1、 Wang, Qi,Zhang, Chao,Yang, Jun. "Synthesis of ACE tricyclic systems of daphnicyclidin A and dehy-droxymacropodumine A". supporting information. p. 1906 - 1910. Retrieved 2019/12/27.
• 2、 Jyothi, Divya,Suresh, Hariprasad. "Five- and six-membered cyclic α-acylvinyl anionic synthons: Synthesis of α-trimethylsilyl-α,β-unsaturated cycloalkenones and their conversion into 2-(hydroxydimethylsilyl)cycloalk-2-enones through carbon-silicon bond scission". experimental part. p. 194 - 203. Retrieved 2012/05/20.