1-Thiaspiro[4.4]non-3-en-6-one(9CI)

Base Information

• Chemical Name: 1-Thiaspiro[4.4]non-3-en-6-one(9CI)
• CAS No.: 630059-87-9
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.233
• Mol file: 630059-87-9.mol

Synonyms:1-THIASPIRO[4.4]NON-3-EN-6-ONE;

Chemical Property of 1-Thiaspiro[4.4]non-3-en-6-one(9CI)

Chemical Property:

• PSA: 42.37000
• LogP: 1.78120

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Thiaspiro[4.4]non-3-en-6-one(9CI)

There total 1 articles about 1-Thiaspiro[4.4]non-3-en-6-one(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: 91.0%

(4R,5R)-4-Phenylselanyl-1-thia-spiro[4.4]nonan-6-one → 1-thia-spiro[4.4]non-3-en-6-one (630059-87-9,630060-02-5,630060-06-9)

Guidance literature:

(4R,5R)-4-Phenylselanyl-1-thia-spiro[4.4]nonan-6-one; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.666667h;

With pyridine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo030196w

Reference yield: 33.0%

(R)-Mandelic Acid (611-71-2) + 1-thia-spiro[4.4]non-3-en-6-one (630059-87-9,630060-02-5,630060-06-9) → (3R,5S,6S)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one (630059-93-7) + (3R,5S,6R)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one (630059-90-4) + (3R,5R,6S)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one (630059-96-0) + (3R,5R,6R)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one (630059-99-3)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In dichloromethane; acetonitrile; for 48h; Heating;

DOI:10.1021/jo030196w

Reference yield:

1-thia-spiro[4.4]non-3-en-6-one (630059-87-9,630060-02-5,630060-06-9) → Benzoic acid (5S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-1-thia-spiro[4.4]non-3-yl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: 37 percent / Sc(OTf)3 / CH₂Cl₂; acetonitrile / 48 h / Heating

2.1: 91 percent / H₂ / Pd/C / ethyl acetate / 48 h / 20 °C / 760 Torr

3.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 4 h

4.1: 51 percent / LiAlH₄ / diethyl ether / 4 h

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6.1: 90 percent / NaIO₄/SiO₂ / CH₂Cl₂; hexane / 24 h

7.1: NaOAc / 4 h / 110 °C

7.2: 30 percent / p-toluenesulfonic acid / benzene / 12 h / Heating

8.1: 9-BBN / tetrahydrofuran

8.2: 62 percent / NaOH; H₂O₂

9.1: 98 percent / DMAP; pyridine / 4 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium periodate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium acetate; silica gel; scandium tris(trifluoromethanesulfonate); palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile; 7.1: Pummerer rearrangement;

DOI:10.1021/jo030196w

Downstream raw materials:

(3R,5S,6S)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one

(3R,5S,6R)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one

(3R,5R,6S)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one

(3R,5R,6R)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one