5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]

Base Information

• Chemical Name: 5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]
• CAS No.: 20200-59-3
• Molecular Formula: C₂₄H₂₃NO₂
• Molecular Weight: 357.452
• European Community (EC) Number: 622-649-4
• DSSTox Substance ID: DTXSID10403083
• Nikkaji Number: J1.441.528I
• Mol file: 20200-59-3.mol

Synonyms:20200-59-3;5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran];5'-methoxy-1',3',3'-trimethylspiro[benzo[f]chromene-3,2'-indole];5'-Methoxy-1',3',3'-trimethylspiro[benzo[f]chromene-3,2'-indoline];ChemDivAM_000904;ST50319518;ChemDiv1_021457;Oprea1_522150;SCHEMBL1629606;HMS647P07;DTXSID10403083;AKOS001626580;AKOS021989608;EU-0037849;SR-01000430579;SR-01000430579-1;5'-METHOXY-1',3',3'-TRIMETHYL-1',3'-DIHYDROSPIRO[BENZO[F]CHROMENE-3,2'-INDOLE]

Chemical Property of 5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]

Chemical Property:

• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 357.172878976
• Heavy Atom Count: 27
• Complexity: 601

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C=CC(=C2)OC)N(C13C=CC4=C(O3)C=CC5=CC=CC=C54)C)C

Technology Process of 5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]

There total 6 articles about 5-Methoxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran] 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: 73.0%

5-methoxy-1,2,3,3-tetramethyl-3H-indolium iodide (57019-81-5) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 5'-methoxy-1',3',3'-trimethylspiro[benzo[ ]chromene-3,2'-indoline] (20200-59-3)

Guidance literature:

With triethylamine; In ethanol; for 23h; Reflux;

DOI:10.1021/acs.joc.6b01193

Reference yield:

3-methyl-butan-2-one (563-80-4) → 5'-methoxy-1',3',3'-trimethylspiro[benzo[ ]chromene-3,2'-indoline] (20200-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / 5.5 h / Reflux

2: acetonitrile / 21 h / Reflux

3: triethylamine / ethanol / 23 h / Reflux

With acetic acid; triethylamine; In ethanol; acetonitrile; 1: |Fischer Indole Synthesis;

DOI:10.1021/acs.joc.6b01193

Reference yield:

5-Methoxy-2,3,3-trimethyl-3H-indole (31241-19-7) → 5'-methoxy-1',3',3'-trimethylspiro[benzo[ ]chromene-3,2'-indoline] (20200-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 21 h / Reflux

2: triethylamine / ethanol / 23 h / Reflux

With triethylamine; In ethanol; acetonitrile;

DOI:10.1021/acs.joc.6b01193

upstream raw materials:

1,3,3-trimethyl-5-methoxy-2-methyleneindoline

2-hydroxynaphthalene-1-carbaldehyde

5-methoxy-1,2,3,3-tetramethyl-3H-indolium iodide

3-methyl-butan-2-one