2-Phenylazepane

Base Information

• Chemical Name: 2-Phenylazepane
• CAS No.: 3466-82-8
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Hs Code.: 2933990090
• European Community (EC) Number: 862-926-9
• DSSTox Substance ID: DTXSID70403201
• Nikkaji Number: J574.147E
• Mol file: 3466-82-8.mol

Synonyms:2-phenylazepane;3466-82-8;2-Phenyl-azepane;MFCD02663698;2-Phenylperhydroazepine;2-phenylazacycloheptane;2-phenylazepane, AldrichCPR;Oprea1_689476;2-Phenylhexahydro-1H-azepine;2-(R,S)-phenylazacycloheptane;SCHEMBL2707245;DTXSID70403201;QFRVVKIFIHGQCH-UHFFFAOYSA-N;BBL020502;STK893195;AKOS005144051;p-Aminomethyl-hydrozimtsaeure-methylester;FT-0651327;EN300-58298;A25686;N12399;Z1258578207

Chemical Property of 2-Phenylazepane

Chemical Property:

• Vapor Pressure: 0.00502mmHg at 25°C
• Refractive Index: 1.499
• Boiling Point: 276.8 °C at 760 mmHg
• Flash Point: 123.3 °C
• PSA: 12.03000
• Density: 0.95 g/cm³
• LogP: 3.22010
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 175.136099547
• Heavy Atom Count: 13
• Complexity: 138

Purity/Quality:

98%min ^*data from raw suppliers

2-Phenylazepane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(NCC1)C2=CC=CC=C2
• Uses: 2-Phenylazepane can be used in the preparation of pyrrolylphenylsulfonates as dopamine D3 antagonists as well as in the preparation of substituted amidothiophene derivatives for use as 11-β-HSD1 inhibitors. Can be used in the preparation of pyrrolylphenylsulfonates as dopamine D3 antagonists as well as in the preparation of substituted amidothiophene derivatives for use as 11-β-HSD1 inhibitors.

Technology Process of 2-Phenylazepane

There total 12 articles about 2-Phenylazepane 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: 89.0%

2-phenyl-4,5,6,7-tetrahydro-3H-azepine (3338-00-9) → 2-phenylazacycloheptane (3466-82-8)

Guidance literature:

With titanocene dichloride; butyl magnesium bromide; In diethyl ether; at 25 ℃; for 15h;

DOI:10.1016/S0040-4039(97)01797-8

Reference yield: 55.0%

hexamethylene imine (111-49-9) + phenyllithium (591-51-5) → 2-phenylazacycloheptane (3466-82-8)

Guidance literature:

hexamethylene imine; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.166667h;

With 2,2-dimethylpropiophenone; In diethyl ether; hexane; at -78 ℃;

phenyllithium; In diethyl ether; hexane; at -78 - 20 ℃; regioselective reaction;

DOI:10.1038/NCHEM.2871

Reference yield:

caprolactam (105-60-2,9012-16-2) → 2-phenylazacycloheptane (3466-82-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / n-BuLi / CH₂Cl₂ / -78 - 20 °C

2: 45 percent / tetrahydrofuran / -70 - 20 °C

3: TFA / 2 h / 18 - 22 °C

4: 75 mg / NaBH₄ / H₂O; methanol / 18 - 22 °C

With sodium tetrahydroborate; n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol035746r

upstream raw materials:

cyclohexanone O-(ethoxycarbonyl)oxime

cyclohexanone oxime methanesulfonate

2-phenyl-4,5,6,7-tetrahydro-3H-azepine

hexamethylene imine

Downstream raw materials:

2-Phenyl-1-<(trimethylsilyl)methyl>perhydroazepine

1-nitroso-2-phenylperhydroazepine

Refernces

• 1、 Abbott, Belinda M.,Dahanayake, Darani,Glab, Jason A.,Mbogo, George W.,Puthalakath, Hamsa,Richards, Benjamin J.,Smith, Brian J.. "Discovery, synthesis and exploration of N-benzylsulfonyl-2-phenylazepanes as inhibitors of Bim expression in a mouse embryonic fibroblast model". . . Retrieved 2022/02/07.
• 2、 Chen, Weijie,Ma, Longle,Paul, Anirudra,Seidel, Daniel. "Direct α-C-H bond functionalization of unprotected cyclic amines". . p. 165 - 169. Retrieved 2018/02/06.