3-methyl-3,4-dihydro-2H-isoquinolin-1-one

Base Information

• Chemical Name: 3-methyl-3,4-dihydro-2H-isoquinolin-1-one
• CAS No.: 35690-67-6
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.203
• DSSTox Substance ID: DTXSID30385110
• ChEMBL ID: CHEMBL1438811
• Mol file: 35690-67-6.mol

Synonyms:35690-67-6;3-methyl-3,4-dihydro-2H-isoquinolin-1-one;3-methyl-1,2,3,4-tetrahydroisoquinolin-1-one;1(2H)-Isoquinolinone, 3,4-dihydro-3-methyl-;MLS000104367;3-methyl-3,4-dihydroisoquinolin-1(2H)-one;SCHEMBL6448571;CHEMBL1438811;SCHEMBL11742766;DTXSID30385110;HMS2301J17;3-methyl-3,4-dihydro-1-isoquinolone;AKOS013604439;SMR000054302;MC 259835;EN300-133887;A822940;Z1218937049

Chemical Property of 3-methyl-3,4-dihydro-2H-isoquinolin-1-one

Chemical Property:

• PSA: 32.59000
• LogP: 1.37140
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

98% ^*data from raw suppliers

3-Methyl-3,4-dihydro-2H-isoquinolin-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC=CC=C2C(=O)N1

Technology Process of 3-methyl-3,4-dihydro-2H-isoquinolin-1-one

There total 5 articles about 3-methyl-3,4-dihydro-2H-isoquinolin-1-one 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%

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + N-(pivaloyloxy)benzamide (61650-22-4) → 3,4-dihydro-3-methylisoquinolin-1-(2H)-one (35690-67-6) + 4-methyl-3,4-dihydro-2H-isoquinolin-1-one (70079-42-4)

Guidance literature:

With C₃₂H₅₄Cl₄Rh₂; cesium pivalate; In 2,2,2-trifluoroethanol; at 40 ℃; for 18h; under 760.051 Torr; regioselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.9b02029

Reference yield: 0.9%

N-benzoyl-3-methyl-1,2,3,4-tetrahydroisoquinoline → 3,4-dihydro-3-methylisoquinolin-1-(2H)-one (35690-67-6) + N-[2-(2-Formyl-phenyl)-1-methyl-ethyl]-benzamide

Guidance literature:

In ethanol; at 28 ℃; for 72h; culture of fungus Cunninghamella elegans Lendner;

Reference yield:

2,3-dihydro-2-methyl-1H-inden-1-one (17496-14-9) → 3-methyl-3,4-dihydroquinolin-2(1H)-one (31883-79-1) + 3,4-dihydro-3-methylisoquinolin-1-(2H)-one (35690-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux

2.1: (Ir[dF(CF₃)ppy]₂(dtbpy))PF₆; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere; Irradiation

2.2: 20 h / 20 °C / Inert atmosphere; Darkness

With (Ir[dF(CF₃)ppy]₂(dtbpy))PF₆; hydroxylamine hydrochloride; sodium acetate; N,N-dimethyl-formamide; In ethanol; water; 2.1: |Beckmann Rearrangement / 2.2: |Beckmann Rearrangement;

DOI:10.1021/jacs.1c10148

upstream raw materials:

2-methylindanone oxime

2-methyl-3-phenylpropionohydroxamic acid

propene

N-(pivaloyloxy)benzamide

Downstream raw materials:

7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline

2-methyl-3,4-dihydro-2H-isoquinolin-1-one

Refernces

• 1、 Barber, Joyann S.,Scales, Stephanie,Tran-Dubé, Michelle,Wang, Fen,Sach, Neal W.,Bernier, Louise,Collins, Michael R.,Zhu, Jinjiang,McAlpine, Indrawan J.,Patman, Ryan L.. "Rhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones". supporting information. p. 5689 - 5693. Retrieved 2019/08/01.
• 2、 Potapov, V.M.,Dem'yanovich, V. M.,Vendrova, O. E.,Khlebnikov, V. A.. "INTRAMOLECULAR AMIDATION OF ARYLALKYLHYDROXAMIC ACIDS". . p. 528 - 533. Retrieved 2007/10/02.