Bicyclo[2.2.1]hept-2-ene-1-carboxylic acid, methyl ester

Base Information

Chemical Name:Bicyclo[2.2.1]hept-2-ene-1-carboxylic acid, methyl ester
CAS No.:15023-46-8
Molecular Formula:C9H12O2
Molecular Weight:152.193
Hs Code.:
Mol file:15023-46-8.mol

Synonyms:

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Chemical Property of Bicyclo[2.2.1]hept-2-ene-1-carboxylic acid, methyl ester

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Technology Process of Bicyclo[2.2.1]hept-2-ene-1-carboxylic acid, methyl ester

There total 1 articles about Bicyclo[2.2.1]hept-2-ene-1-carboxylic acid, methyl 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:

: 51789-95-8
bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid ethyl ester

: 15023-46-8
methyl bicyclo[2.2.1]hept-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 6 h / 75007.5 Torr

2.1: sodium hydroxide / water; methanol / 20 °C

2.2: pH 3

3.1: bromine; phosphorus trichloride / 90 °C

4.1: sulfuric acid / 12 h / Reflux

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C

With sulfuric acid; 10 wt% Pd(OH)2 on carbon; hydrogen; bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; phosphorus trichloride; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.04.004

Reference yield:

: 15023-46-8
methyl bicyclo[2.2.1]hept-2-ene-1-carboxylate

: 75421-01-1
exo-Tricyclo<3.2.1.0^2,4>octyl-1-carbinyl Tosylate

Guidance literature:: Multi-step reaction with 3 steps

1: Zn-Cu, I₂, / diethyl ether / 48 h / Heating

2: 62 percent / LAH / diethyl ether / 2 h / Heating

3: pyridine / 0 °C

With lithium aluminium tetrahydride; iodine; copper; zinc; In pyridine; diethyl ether;
DOI:10.1021/jo01314a054

Reference yield:

: 15023-46-8
methyl bicyclo[2.2.1]hept-2-ene-1-carboxylate

: methyl (2S)-2-{[({(1R*,3R*,4R*)-3-[6-(cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]heptan-1-yl}methoxy) (phenoxy)phosphoryl]amino}propanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: mercury(II) diacetate / water; tetrahydrofuran / 2 h

1.2: 0.5 h

1.3: 0.17 h

2.1: 0.17 h

3.1: pyridinium dichromate / dichloromethane / 20 °C / Molecular sieve

4.1: sodium tetrahydroborate / methanol / 0 - 20 °C

5.1: pyridine / 3 h / 0 - 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 115 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 2 h / 160 °C / Microwave irradiation; Sealed tube

9.1: ethanol / 0.5 h / 140 °C / Microwave irradiation

10.1: tert-butylmagnesium chloride / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; pyridinium dichromate; tert-butylmagnesium chloride; mercury(II) diacetate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1016/j.bmc.2014.11.011