Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)

Base Information

• Chemical Name: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)
• CAS No.: 124150-82-9
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.182
• Mol file: 124150-82-9.mol

Synonyms:Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)

Chemical Property of Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)

Chemical Property:

• PSA: 34.14000
• LogP: 1.04650

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)

There total 6 articles about Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (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:

(1aS,1bR,4S,5aR)-4-tert-Butyl-1,1,1b-trimethyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-ol (124062-50-6) → (1R,3S)-3-Acetyl-2,2-dimethyl-cyclopropanecarbaldehyde (124150-82-9)

Guidance literature:

With tetrabutylammonium dihydrogen phosphate; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85604-0

Reference yield:

(3S,7aR)-3-tert-Butyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (124062-47-1) → (1R,3S)-3-Acetyl-2,2-dimethyl-cyclopropanecarbaldehyde (124150-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) LDA, PhSeBr; 2) hydrogen peroxide / 1) -78 deg C, THF, 4 h;

2: 1) Et₂O, 25 deg C, 19 h; 2) UV lamp irradiation, 4 h

3: 0.7 eq. RED-Al / tetrahydrofuran / 25 °C

4: tetrabutyl ammonium dihydrogen phosphate / CH₂Cl₂; H₂O / 96 h / 25 °C

With Phenylselenyl bromide; dihydrogen peroxide; tetrabutylammonium dihydrogen phosphate; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4039(00)99569-8

Reference yield:

(3S,7aR)-3-tert-Butyl-7a-methyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one (124062-48-2) → (1R,3S)-3-Acetyl-2,2-dimethyl-cyclopropanecarbaldehyde (124150-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Et₂O, 25 deg C, 19 h; 2) UV lamp irradiation, 4 h

2: 0.7 eq. RED-Al / tetrahydrofuran / 25 °C

3: tetrabutyl ammonium dihydrogen phosphate / CH₂Cl₂; H₂O / 96 h / 25 °C

With tetrabutylammonium dihydrogen phosphate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4039(00)99569-8

upstream raw materials:

(1aS,1bR,4S,5aR)-4-tert-Butyl-1,1,1b-trimethyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-ol

(3S,7aR)-3-tert-Butyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,7aR)-3-tert-Butyl-7a-methyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one

(1aS,1bR,4S,5aR)-4-tert-Butyl-1,1,1b-trimethyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one