2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester

Base Information

• Chemical Name: 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester
• CAS No.: 195703-08-3
• Molecular Formula: C₃₅H₅₂O₅
• Molecular Weight: 552.795
• Mol file: 195703-08-3.mol

Synonyms:2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester

Chemical Property of 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester

There total 5 articles about 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester 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: 74.0%

t-butyl malonate (541-16-2) + (E)-1-Phenyl-4-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-but-2-en-1-one → 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester (195703-08-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

DOI:10.1016/S0960-894X(97)00357-0

Reference yield:

methyl 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetate (31751-83-4) → 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester (195703-08-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / LiAlH₄ / diethyl ether / 0.25 h / 0 °C

2: 91 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

3: 88 percent / toluene / 24 h / Ambient temperature

4: 74 percent / NaH / tetrahydrofuran / 5 h / 0 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0960-894X(97)00357-0

Reference yield:

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol (31207-73-5) → 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester (195703-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

2: 88 percent / toluene / 24 h / Ambient temperature

3: 74 percent / NaH / tetrahydrofuran / 5 h / 0 - 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0960-894X(97)00357-0

upstream raw materials:

t-butyl malonate

methyl 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetate

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetaldehyde