(-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane

Base Information

• Chemical Name: (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane
• CAS No.: 240802-42-0
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.161
• Mol file: 240802-42-0.mol

Synonyms:(-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane

Chemical Property of (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane

There total 8 articles about (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane 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:

3-Hydroxyindene (61463-21-6,109380-06-5,109431-69-8,112836-60-9,56631-57-3) → 1H-inden-1-one (480-90-0) + (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane (240802-42-0) + 6,6a-dihydro-1aH-1-oxa-cyclopropa[a]inden-6-ol + 6,6a-dihydro-1aH-1-oxa-cyclopropa[a]inden-6-ol

Guidance literature:

With 4-Phenylpyridine 1-oxide; [bis(4,6-t-Bu-salycilydene)-((1S,2S)cyclohexanediamine)Mn]Cl; iodosylbenzene; In dichloromethane; at 20 ℃; Further Variations:; Reagents; Product distribution;

DOI:10.1021/jo010350j

Reference yield:

indan-2-ol (4254-29-9) → (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane (240802-42-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / PBr₃; pyridine / CHCl₃ / 1 h / 0 °C

2: 26 percent / toluene dioxygenase from Pseudomonas putida UV₄ / 24 h

3: CH₃ONa / diethyl ether / 3 h / 20 °C

With pyridine; sodium methylate; phosphorus tribromide; toluene dioxygenase from Pseudomonas putida UV₄; In diethyl ether; chloroform; 1: Substitution / 2: Oxidation / 3: Dehydrobromination;

Reference yield:

2-acetoxyindane (4254-31-3) → (-)-(1S,2R,3S)-1,2-Epoxy-3-hydroxyindane (240802-42-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / toluene dioxygenase from Pseudomonas putida UV₄ / 24 h

2: 43 percent / PBr₃; pyridine / CHCl₃ / 1 h / 0 °C

3: 26 percent / toluene dioxygenase from Pseudomonas putida UV₄ / 24 h

4: CH₃ONa / diethyl ether / 3 h / 20 °C

With pyridine; sodium methylate; phosphorus tribromide; toluene dioxygenase from Pseudomonas putida UV₄; In diethyl ether; chloroform; 1: Hydrolysis / 2: Substitution / 3: Oxidation / 4: Dehydrobromination;

upstream raw materials:

(-)-trans-(1S,3S)-1,3-Dihydroxy-2-chloroindane

(+)-trans-(1S,3S)-1,3-Dihydroxy-2-bromoindane

3-Hydroxyindene

indan-2-ol

Refernces

• 1、 Bowers, Nigel I.,Boyd, Derek R.,Sharma, Narain D.,Goodrich, Peter A.,Groocock, Melanie R.,Blacker, A. John,Goode, Paul,Dalton, Howard. "Stereoselective benzylic hydroxylation of 2-substituted indanes using toluene dioxygenase as biocatalyst". . p. 1453 - 1461. Retrieved 2007/10/03.