Clausine I

Base Information

• Chemical Name: Clausine I
• CAS No.: 182261-94-5
• Molecular Formula: C₁₄H₁₁NO₃
• Molecular Weight: 241.246
• Mol file: 182261-94-5.mol

Synonyms:

Chemical Property of Clausine I

Chemical Property:

• Melting Point: 222-223 °C
• Boiling Point: 515.3±45.0 °C(Predicted)
• PKA: 9.38±0.30(Predicted)
• PSA: 62.32000
• Density: 1.418±0.06 g/cm3(Predicted)
• LogP: 2.84780

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Clausine I

There total 8 articles about Clausine I 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: 100.0%

1-benzyloxy-3-formyl-6-methoxy-9H-carbazole (1069130-74-0) → clausine I (182261-94-5)

Guidance literature:

With aluminum (III) chloride; In 1,4-dioxane; at 101 ℃; for 3h;

DOI:10.1055/s-2008-1077855

Reference yield:

methyl 4-amino-3-(benzyloxy)benzoate (475215-88-4) → clausine I (182261-94-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate / toluene / 64 h / 80 °C / Inert atmosphere

2.1: palladium diacetate; acetic acid / 4 h / 100 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / diethyl ether; toluene / 3.58 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere

5.1: aluminum (III) chloride / 1,4-dioxane / 3 h / 101 °C / Inert atmosphere

5.2: Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; manganese(IV) oxide; aluminum (III) chloride; palladium diacetate; diisobutylaluminium hydride; caesium carbonate; acetic acid; In 1,4-dioxane; diethyl ether; dichloromethane; toluene;

DOI:10.1016/j.tet.2012.05.105

Reference yield:

methyl 3-(benzyloxy)-4-nitrobenzoate (209528-69-8) → clausine I (182261-94-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iron; acetic acid / 4 h / 20 - 40 °C

2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate / toluene / 64 h / 80 °C / Inert atmosphere

3.1: palladium diacetate; acetic acid / 4 h / 100 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / diethyl ether; toluene / 3.58 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere

6.1: aluminum (III) chloride / 1,4-dioxane / 3 h / 101 °C / Inert atmosphere

6.2: Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; manganese(IV) oxide; aluminum (III) chloride; palladium diacetate; iron; diisobutylaluminium hydride; caesium carbonate; acetic acid; In 1,4-dioxane; diethyl ether; dichloromethane; toluene;

DOI:10.1016/j.tet.2012.05.105

upstream raw materials:

1-benzyloxy-3-formyl-6-methoxy-9H-carbazole

methyl 4-amino-3-(benzyloxy)benzoate

methyl 3-(benzyloxy)-4-nitrobenzoate

methyl 3-benzyloxy-4-(4-methoxyphenylamino)benzoate

Refernces

• 1、 B?rger, Carsten,Kn?lker, Hans-Joachim. "Transition metals in organic synthesis, Part 85.1 A general approach to 1,6-dioxygenated carbazole alkaloids - first total synthesis of clausine G, clausine I, and clausine Z". body text. p. 1698 - 1702. Retrieved 2009/05/07.