(+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Base Information

• Chemical Name: (+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene
• CAS No.: 136066-60-9
• Molecular Formula: C₂₁H₂₈O₃Si
• Molecular Weight: 356.537

Synonyms:(+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Chemical Property of (+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

There total 1 articles about (+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene 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: 76.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + (+/-)-3-(2-hydroxy-2-methyl-2-phenylacetoxy)-endo-tricyclo<4.2.1.02,5>non-7-ene (136097-50-2,136173-44-9) → (+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-60-9)

Guidance literature:

at 80 ℃;

DOI:10.1021/ja00020a026

Reference yield: 94.0%

(+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-60-9) → (+/-)-(E)-1-<2-methyl-2-<(trimethylsilyl)oxy>-2-phenylacetoxy>-1,3-butadiene (136097-48-8)

Guidance literature:

at 25 - 250 ℃;

DOI:10.1021/ja00020a026

Reference yield:

(+/-)-3-<2-methyl-2-<(trimethylsilyl)oxo>-2-phenylacetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-60-9) → (R)-2-Hydroxy-2-phenyl-propionic acid (3aR,4S,7aR)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester (136066-52-9,136066-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 25 - 250 °C

2: 2.) aq. oxalic acid / 1.) toluene, 25 deg C, 2.) MeOH, 25 deg C, 1 h

With oxalic acid;

DOI:10.1021/ja00020a026

upstream raw materials:

N,O-bis-(trimethylsilyl)-acetamide

(+/-)-3-(2-hydroxy-2-methyl-2-phenylacetoxy)-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Downstream raw materials:

(+/-)-(E)-1-<2-methyl-2-<(trimethylsilyl)oxy>-2-phenylacetoxy>-1,3-butadiene

(R)-2-Hydroxy-2-phenyl-propionic acid (3aR,4S,7aR)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

(S)-2-Hydroxy-2-phenyl-propionic acid (3aR,4S,7aR)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

(S)-2-Phenyl-2-trimethylsilanyloxy-propionic acid (3aS,4R,7aS)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

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