Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (9CI)
• CAS No.: 350995-88-9
• Molecular Formula: C₉H₁₃NO₄
• Molecular Weight: 199.207
• Mol file: 350995-88-9.mol

Synonyms:Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (9CI)

Chemical Property of Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (9CI)

Chemical Property:

• PSA: 68.12000
• LogP: 0.41460

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (9CI)

There total 3 articles about Bicyclo[2.2.1]heptane-2,3-dione, 7,7-dimethoxy-, monooxime, (1R,4S)- (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: 85.0%

(1S,4R)-(+)-7,7-dimethoxybicyclo<2.2.1>heptan-2-one (83829-13-4) → (+)-3-hydroxyimino-7,7-dimethoxynorbornan-2-one (350995-88-9)

Guidance literature:

With n-Butyl nitrite; potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0957-4166(01)00085-4

Reference yield:

(1R,2S,4S)-7,7-dimethoxy-1,4,5,6-tetrachlorobicyclo<2.2.1>hept-5-en-2-ol (133962-63-7) → (+)-3-hydroxyimino-7,7-dimethoxynorbornan-2-one (350995-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / Na / ethanol; tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

2: 95 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

3: 85 percent / t-BuOK; BuONO / tetrahydrofuran / 12 h / 20 °C

With n-Butyl nitrite; potassium tert-butylate; sodium; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; ammonia;

DOI:10.1016/S0957-4166(01)00085-4

Reference yield:

(-)-(1S,2S,4R)-7,7-dimethoxynorbornan-2-endo-ol (97858-83-8) → (+)-3-hydroxyimino-7,7-dimethoxynorbornan-2-one (350995-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

2: 85 percent / t-BuOK; BuONO / tetrahydrofuran / 12 h / 20 °C

With n-Butyl nitrite; potassium tert-butylate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(01)00085-4

upstream raw materials:

(1S,4R)-(+)-7,7-dimethoxybicyclo<2.2.1>heptan-2-one

(1R,2S,4S)-7,7-dimethoxy-1,4,5,6-tetrachlorobicyclo<2.2.1>hept-5-en-2-ol

(-)-(1S,2S,4R)-7,7-dimethoxynorbornan-2-endo-ol

Refernces