1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI)

Base Information

• Chemical Name: 1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI)
• CAS No.: 810682-41-8
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• Mol file: 810682-41-8.mol

Synonyms:1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI)

Chemical Property of 1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI)

Chemical Property:

• PSA: 35.53000
• LogP: 2.45340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI)

There total 8 articles about 1,3-Dioxaspiro[4.5]decan-7-one,2,2,6,6-tetramethyl-8-methylene-,(5S)-(9CI) 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: 64.0%

methyl iodide (74-88-4) + (S)-2,2,6,6-Tetramethyl-1,3-dioxa-spiro[4.5]decan-7-one (810682-14-5) → (S)-2,2,6,6-Tetramethyl-8-methylene-1,3-dioxa-spiro[4.5]decan-7-one (810682-41-8)

Guidance literature:

(S)-2,2,6,6-Tetramethyl-1,3-dioxa-spiro[4.5]decan-7-one; With eschenmoser's salt; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

methyl iodide; In acetone; for 10h;

DOI:10.1016/j.tetlet.2004.09.143

Reference yield:

(S)-3-hydroxy-2,2-dimethylcyclohexanone (87655-21-8) → (S)-2,2,6,6-Tetramethyl-8-methylene-1,3-dioxa-spiro[4.5]decan-7-one (810682-41-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 1.5 h

2.1: 50 percent / SmI₂; HMPA / tetrahydrofuran / 0.25 h / -78 °C

3.1: aq. H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 10 h

4.1: CSA / 1 h

5.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

6.1: LDA; Eschenmoser's salt / tetrahydrofuran / 1 h / -78 - 0 °C

6.2: 64 percent / acetone / 10 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; samarium diiodide; dihydrogen peroxide; eschenmoser's salt; potassium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 3.1: Tamao oxidation / 5.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2004.09.143

Reference yield:

(1S,3S)-1-Hydroxymethyl-2,2-dimethyl-cyclohexane-1,3-diol (954096-32-3) → (S)-2,2,6,6-Tetramethyl-8-methylene-1,3-dioxa-spiro[4.5]decan-7-one (810682-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CSA / 1 h

2.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

3.1: LDA; Eschenmoser's salt / tetrahydrofuran / 1 h / -78 - 0 °C

3.2: 64 percent / acetone / 10 h

With eschenmoser's salt; Dess-Martin periodane; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; 2.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2004.09.143

upstream raw materials:

methyl iodide

(S)-2,2,6,6-Tetramethyl-1,3-dioxa-spiro[4.5]decan-7-one

(S)-3-hydroxy-2,2-dimethylcyclohexanone

(1S,3S)-1-Hydroxymethyl-2,2-dimethyl-cyclohexane-1,3-diol

Downstream raw materials:

(S)-8-(4-Methoxy-benzyloxymethyl)-2,2,6,6-tetramethyl-1,3-dioxa-spiro[4.5]dec-7-ene

(S)-1-Hydroxymethyl-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enol

Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester

[(S)-4-(4-Methoxy-benzyloxymethyl)-1-methoxymethoxy-2,2-dimethyl-cyclohex-3-enyl]-methanol