2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione

Base Information

• Chemical Name: 2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione
• CAS No.: 899-79-6
• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.382
• European Community (EC) Number: 618-321-5
• Nikkaji Number: J990.767J
• Mol file: 899-79-6.mol

Synonyms:EC 618-321-5;899-79-6;2-[2-(6-METHOXYTETRALIN-1-YLIDENE)-ETHYL]-2-METHYLCYCLOPENTANE-1,3-DIONE;2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione;SCHEMBL373267;PHYRXYUDHILFBN-JLHYYAGUSA-N;3-Methoxy-8,14-secoestra-1,3,5(10),9(11)-tetraen-14,17-dione;1-[2-(6-Methoxytetralin-1-ylidene)ethyl]-1-methylcyclopentane-2,5-dione;2-[(2E)-2-(6-Methoxy-3,4-dihydro-1(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione #

Chemical Property of 2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione

Chemical Property:

• Vapor Pressure: 3.9E-09mmHg at 25°C
• Boiling Point: 473.5°C at 760 mmHg
• Flash Point: 209.3°C
• Density: 1.176g/cm³
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 298.15689456
• Heavy Atom Count: 22
• Complexity: 475

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)CCC1=O)CC=C2CCCC3=C2C=CC(=C3)OC
• Isomeric SMILES: CC1(C(=O)CCC1=O)C/C=C/2\CCCC3=C2C=CC(=C3)OC

Technology Process of 2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione

There total 10 articles about 2-((2E)-2-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)ethyl)-2-methylcyclopentane-1,3-dione 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%

2-Methylcyclopentane-1,3-dione (765-69-5) + 6-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalen-1-ol (3125-36-8) → 2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione (899-79-6)

Guidance literature:

2-Methylcyclopentane-1,3-dione; 6-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalen-1-ol; In 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl alcohol; at 20 ℃; for 0.25h; Inert atmosphere;

With N-benzyl-trimethylammonium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl alcohol; for 2h; Inert atmosphere; Reflux;

DOI:10.1055/a-1328-0352

Reference yield:

6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → 2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione (899-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 6 h / 40 °C / Cooling with ice

2: N-benzyl-trimethylammonium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl alcohol; methanol / 5 h / Reflux

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl alcohol;

DOI:10.1002/anie.201404909

Reference yield:

4-hydroxy-2-methyl-1,3-cyclopentanedione (4800-04-8) → 2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione (899-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / Heating

2: Al(OiPr)3, iPrOH

3: Zn, AcOH

With aluminum isopropoxide; acetic acid; isopropyl alcohol; zinc; In methanol;

DOI:10.1248/cpb.21.697

upstream raw materials:

2-Methylcyclopentane-1,3-dione

6-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalen-1-ol

(2S,3S)-3-Hydroxy-2-{2-[6-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-ethyl}-2-methyl-cyclopentanone

6-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalene

Downstream raw materials:

(8S,13S,14S)-14-hydroxy-3-methoxy-13-methyl-6,7,8,12,13,14,15,16-octahydro-17H-cyclopenta[a]phenanthren-17-one

3-methoxy-estra-1,3,5⁽¹⁰⁾,8⁽⁹⁾,14⁽¹⁵⁾-pentaene-17-one

C₁₉H₂₂O₃

(R)-3-methoxy-13-methyl-11,12,13,16-tetrahydro-6H-cyclopenta[α]phenanthren-17(7H)-one

Refernces

• 1、 -. "Total synthesis preparation method of estrone". Paragraph 0045-0048. . Retrieved 2020/02/19.
• 2、 Prevost, Sebastien,Dupre, Nathalie,Leutzsch, Markus,Wang, Qinggang,Wakchaure, Vijay,List, Benjamin. "Catalytic asymmetric torgov cyclization: A concise total synthesis of (+)-estrone". supporting information. p. 8770 - 8773. Retrieved 2014/08/18.