8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene

Base Information

• Chemical Name: 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene
• CAS No.: 152999-94-5
• Molecular Formula: C₁₃H₂₁IO₂
• Molecular Weight: 336.213
• Mol file: 152999-94-5.mol

Synonyms:8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene

Chemical Property of 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene

There total 1 articles about 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-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:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene (152999-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / BF₃*Et₂O / CH₂Cl₂

2: 97 percent / HCl / tetrahydrofuran

3: 1.) n-BuLi, n-Bu₃SnCl; 2.) I₂ / 1.) THF-TMEDA; 2.) CH₂Cl₂

With hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; tributyltin chloride; iodine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)61711-2

Reference yield: 51.0%

benzaldehyde (100-52-7) + 8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene (152999-94-5) → phenyl-(3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-en-8-yl)-methanol

Guidance literature:

8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene; With tert.-butyl lithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.516667h;

benzaldehyde; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1055/s-1999-2889

Reference yield:

8-Iodo-3,3,7,7-tetramethyl-1,5-dioxa-spiro[5.5]undec-8-ene (152999-94-5) → (S)-5-{(R)-[(1S,2R)-2-(2-Hydroxy-ethyl)-2-methyl-cyclohexyl]-methoxy-methyl}-3-iodo-2,4,4-trimethyl-cyclohex-2-enone

Guidance literature:

Multi-step reaction with 11 steps

1: t-BuLi / tetrahydrofuran

2: 96 percent / TBAF / tetrahydrofuran

3: 76 percent / H₂ / Rh on Al₂O₃

4: 100 percent / imidazole / dimethylformamide

5: 85 percent / NaH / dimethylformamide

6: 94 percent / p-TSA / acetone

7: 90 percent / LDA / tetrahydrofuran

8: 73 percent / KHMDS / tetrahydrofuran

9: 1.) (n-Bu₃Sn)(n-Bu)CuCNLi₂; 2.) I₂ / 1.) THF; 2.) THF

10: 62 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂

11: 91 percent / TBAF (pH 7) / tetrahydrofuran

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; (n-Bu₃Sn)(n-Bu)CuCNLi₂; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; rhodium on alumina; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61711-2

upstream raw materials:

2,2-dimethyl-1,3-cyclohexanedione