Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (9CI)

Base Information

• Chemical Name: Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (9CI)
• CAS No.: 172016-29-4
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.204
• Mol file: 172016-29-4.mol

Synonyms:Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (9CI)

Chemical Property of Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (9CI)

Chemical Property:

• PSA: 26.02000
• LogP: 2.08630

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (9CI)

There total 28 articles about Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-amine (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:

Tricyclo[4.2.2.01,6]deca-2,4,9-triene-7-carboxylic acid (172016-33-0) → Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-ylamine (172016-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine, (PhO)2P(O)N₃ / benzene / 20 h / Heating

2: 18 h / Heating

3: 1.) NaHCO₃, Me₂SO₄, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H₂O, 40 deg C, 2 h

With sodium hydroxide; diphenyl phosphoryl azide; sodium hydrogencarbonate; triethylamine; dimethyl sulfate; In benzene;

Reference yield:

1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1) → Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-ylamine (172016-29-4)

Guidance literature:

Multi-step reaction with 16 steps

1: Ph₂C=O / Irradiation

2: LiAlH₄

3: p-TsOH

4: Na/NH₃

5: 60percent aq. AcOH

6: pyridine

7: 1.) MeSCH₂S(O)Me, 2.) BuLi, 3.) H₂SO₄

8: C₅H₅NHBr₃, pyridine / CH₂Cl₂

9: LiCl, Li₂CO₃, HMPA

10: EtONa / benzene

11: p-TsN₃, triethylamine / diethyl ether

12: Irradiation

13: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C

14: triethylamine, (PhO)2P(O)N₃ / benzene / 20 h / Heating

15: 18 h / Heating

16: 1.) NaHCO₃, Me₂SO₄, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H₂O, 40 deg C, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 4-toluenesulfonyl azide; benzophenone; sulfuric acid; diphenyl phosphoryl azide; ammonia; sodium ethanolate; sodium; lithium carbonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; triethylamine; dimethyl sulfate; lithium chloride; methyl methylsulfinylmethyl sulfide; In methanol; diethyl ether; dichloromethane; benzene;

Reference yield:

Bicyclo<4.3.0>nona-1(6),3-dien-7-one (75781-80-5) → Tricyclo[4.2.2.01,6]deca-2,4,9-trien-7-ylamine (172016-29-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 26 h / Irradiation

2: NaBH₄ / methanol / 16 h / Ambient temperature

3: Na/NH₃ / diethyl ether / 3.5 h

4: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 20 min

5: MeONa / benzene / 18.5 h / 12 °C

6: TsN₃, triethylamine / CH₂Cl₂ / 24 h / 20 °C

7: 86 percent / triethylamine / methanol / 24 h / Irradiation

8: pyridine, pyridinium bromide perbromide / CH₂Cl₂ / 3.5 h / 0 °C

9: LiCl, Li₂CO₃, HMPA / 42 h / 40 - 100 °C

10: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C

11: triethylamine, (PhO)2P(O)N₃ / benzene / 20 h / Heating

12: 18 h / Heating

13: 1.) NaHCO₃, Me₂SO₄, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H₂O, 40 deg C, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; 4-toluenesulfonyl azide; oxalyl dichloride; diphenyl phosphoryl azide; ammonia; sodium methylate; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; dimethyl sulfate; lithium chloride; In methanol; diethyl ether; dichloromethane; benzene;

upstream raw materials:

C₁₅H₂₀NO₂S⁽¹⁺⁾*CH₃O₄S^(1-)

Tricyclo[4.2.2.0^1,6]deca-2,4,9-trien-7-yl-carbamic acid 2-methylsulfanyl-ethyl ester

1,4-cyclohexadiene-1,2-dicarboxylic anhydride

Bicyclo<4.3.0>nona-1(6),3-dien-7-one

Downstream raw materials:

<4.2.2>propella-2,4,7,9-tetraene

Refernces

• 1、 Tsuji, Takashi,Nishida, Shinya. "SYNTHESES AND PROPERTIES OF 2,5-ETHENOPROPELLA-3,7,9-TRIENE AND ITS DERIVATIVES". . p. 3361 - 3364. Retrieved 2007/10/02.