2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-dione

Base Information

• Chemical Name: 2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-dione
• CAS No.: 111373-35-4
• Molecular Formula: C₁₇H₁₃IO₂
• Molecular Weight: 376.194
• DSSTox Substance ID: DTXSID901234221
• Mol file: 111373-35-4.mol

Synonyms:SCHEMBL7597609;DTXSID901234221;111373-35-4;2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-dione

Chemical Property of 2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-dione

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 375.99603
• Heavy Atom Count: 20
• Complexity: 369

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CCC2C(=O)C3=CC=CC=C3C2=O)I

Technology Process of 2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-dione

There total 13 articles about 2-[2-(2-Iodophenyl)ethyl]-1H-indene-1,3(2H)-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: 99.0%

3-[3-(2-Iodo-phenyl)-prop-(Z)-ylidene]-3H-isobenzofuran-1-one (111373-34-3,111373-37-6) → 2-[2-(2-Iodo-phenyl)-ethyl]-indan-1,3-dione (111373-35-4)

Guidance literature:

With lithium ethoxide; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1016/S0040-4039(00)95678-8

Reference yield:

2-Iodobenzoic acid (88-67-5) → 2-[2-(2-Iodo-phenyl)-ethyl]-indan-1,3-dione (111373-35-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / BH₃SMe₂ / tetrahydrofuran / 12 h / Ambient temperature

2: 91 percent / tetrahydrofuran / 5 h / 0 deg C to reflux

3: 97 percent / dimethylformamide; tetrahydrofuran / 6 h / 0 deg C to room temperature

4: 95 percent / NaCl, H₂O / dimethylsulfoxide / 15 h / 180 °C

5: 73 percent / i-Bu₂AlH / tetrahydrofuran / 2 h / -50 deg C to -30 deg C

6: 81 percent / PCC, Celite, Molecular Sieves / CH₂Cl₂ / 1 h / Ambient temperature

7: 1.) LDA / 1.) THF, -50 deg C, 30 min 2.) -78 deg C, 5 min

8: 98 percent / TEA / CH₂Cl₂ / 1.5 h / 0 deg C to room temperature

9: 100 percent / DBU / tetrahydrofuran / 2 h / Ambient temperature

10: 99 percent / LiOEt / tetrahydrofuran / 1 h / 25 °C

With molecular sieve; dimethylsulfide borane complex; Celite; TEA; water; lithium ethoxide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95678-8

Reference yield:

2-iodobenzyl alcohol (5159-41-1) → 2-[2-(2-Iodo-phenyl)-ethyl]-indan-1,3-dione (111373-35-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / tetrahydrofuran / 5 h / 0 deg C to reflux

2: 97 percent / dimethylformamide; tetrahydrofuran / 6 h / 0 deg C to room temperature

3: 95 percent / NaCl, H₂O / dimethylsulfoxide / 15 h / 180 °C

4: 73 percent / i-Bu₂AlH / tetrahydrofuran / 2 h / -50 deg C to -30 deg C

5: 81 percent / PCC, Celite, Molecular Sieves / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) LDA / 1.) THF, -50 deg C, 30 min 2.) -78 deg C, 5 min

7: 98 percent / TEA / CH₂Cl₂ / 1.5 h / 0 deg C to room temperature

8: 100 percent / DBU / tetrahydrofuran / 2 h / Ambient temperature

9: 99 percent / LiOEt / tetrahydrofuran / 1 h / 25 °C

With molecular sieve; Celite; TEA; water; lithium ethoxide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95678-8

upstream raw materials:

3-[3-(2-Iodo-phenyl)-prop-(Z)-ylidene]-3H-isobenzofuran-1-one

1H-indene-1,3(2H)-dione

2-(2'-bromoethyl)-1-iodobenzene

2-(2-iodophenyl)ethan-1-ol

Refernces

• 1、 Ciufolini, Marco A.,Browne, Margaret E.. "EFFICIENT PALLADIUM-MEDIATED SYNTHESIS OF A SPIROCYCLIC MODEL FOR FREDERICAMYCIN A.". . p. 171 - 174. Retrieved 2007/10/02.