Ccris 1702

Base Information

• Chemical Name: Ccris 1702
• CAS No.: 2213-00-5
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• UNII: MQ4LN968Y9
• Nikkaji Number: J445.413H
• Mol file: 2213-00-5.mol

Synonyms:Methyl marasmate;CCRIS 1702;MQ4LN968Y9;Cycloprop[e]indene-1a(1H)-carboxylic acid, 6,6a-diformyl-1b,2,3,4,4a,6a-hexahydro-3,3-dimethyl-, methyl ester, (1aS,1bS,4aS,6aR)-;Cycloprop[e]indene-6b(1H)-carboxylic acid, 1a,2-diformyl-1a,3a,4,5,6,6a-hexahydro-5,5-dimethyl-, methyl ester, [1aR-(1aalpha,3abeta,6abeta,6balpha)]-

Chemical Property of Ccris 1702

Chemical Property:

• Vapor Pressure: 9.72E-06mmHg at 25°C
• Refractive Index: 1.4350 (estimate)
• Boiling Point: 372.3°Cat760mmHg
• Flash Point: 162.6°C
• PSA: 60.44000
• Density: 1.319g/cm³
• LogP: 1.92610
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 276.13615911
• Heavy Atom Count: 20
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C=C(C3(CC3(C2C1)C(=O)OC)C=O)C=O)C
• Isomeric SMILES: CC1(C[C@H]2C=C([C@@]3(C[C@@]3([C@H]2C1)C(=O)OC)C=O)C=O)C

Technology Process of Ccris 1702

There total 30 articles about Ccris 1702 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:

3-bromomethyl-2-butenolide (61934-55-2) → (1aR,3aR,6aS,6bS)-1a,2-Diformyl-5,5-dimethyl-1a,3a,4,5,6,6a-hexahydro-1H-cyclopropa[e]indene-6b-carboxylic acid methyl ester (2213-00-5,26575-49-5,75918-37-5,75918-38-6,77698-80-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / Heating

2: 80 percent / NaH / dimethylformamide / 0.5 h / -5 - 0 °C

3: 2.) KO-t-Bu / 1.) toluene, 200 deg C, 0.5 h, 2.) ether, 0 deg C, 0.5 h

4: p-TsOH / methanol / 12 h / 65 °C

5: NEt₃ / CH₂Cl₂ / 0.5 h / -5 °C

6: DBU / tetrahydrofuran / 8 h / 65 °C

7: 2 h / Ambient temperature

8: DIBAL-H / toluene; tetrahydrofuran / 12 h / -78 °C

9: MCPBA / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C -> room temperature, 4.5 h

With potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00543a063

Reference yield:

3-Methylbutenoic acid (541-47-9) → (1aR,3aR,6aS,6bS)-1a,2-Diformyl-5,5-dimethyl-1a,3a,4,5,6,6a-hexahydro-1H-cyclopropa[e]indene-6b-carboxylic acid methyl ester (2213-00-5,26575-49-5,75918-37-5,75918-38-6,77698-80-7)

Guidance literature:

Multi-step reaction with 11 steps

1: NBS / CCl₄

2: NaOH / H₂O / Ambient temperature

3: 90 percent / Heating

4: 80 percent / NaH / dimethylformamide / 0.5 h / -5 - 0 °C

5: 2.) KO-t-Bu / 1.) toluene, 200 deg C, 0.5 h, 2.) ether, 0 deg C, 0.5 h

6: p-TsOH / methanol / 12 h / 65 °C

7: NEt₃ / CH₂Cl₂ / 0.5 h / -5 °C

8: DBU / tetrahydrofuran / 8 h / 65 °C

9: 2 h / Ambient temperature

10: DIBAL-H / toluene; tetrahydrofuran / 12 h / -78 °C

11: MCPBA / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C -> room temperature, 4.5 h

With sodium hydroxide; N-Bromosuccinimide; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00543a063

Reference yield:

(Z)-2-Bromo-7,7-dimethoxy-5,5-dimethyl-hept-2-en-1-ol (75887-39-7) → (1aR,3aR,6aS,6bS)-1a,2-Diformyl-5,5-dimethyl-1a,3a,4,5,6,6a-hexahydro-1H-cyclopropa[e]indene-6b-carboxylic acid methyl ester (2213-00-5,26575-49-5,75918-37-5,75918-38-6,77698-80-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / methanol / 2.5 h / 50 °C

2: pyridine / 1 h / 0 °C

3: 2N H₂SO₄/HOAc / H₂O / 2 h / 0 °C

4: 80 percent / NaH / dimethylformamide / 0.5 h / -5 - 0 °C

5: 2.) KO-t-Bu / 1.) toluene, 200 deg C, 0.5 h, 2.) ether, 0 deg C, 0.5 h

6: p-TsOH / methanol / 12 h / 65 °C

7: NEt₃ / CH₂Cl₂ / 0.5 h / -5 °C

8: DBU / tetrahydrofuran / 8 h / 65 °C

9: 2 h / Ambient temperature

10: DIBAL-H / toluene; tetrahydrofuran / 12 h / -78 °C

11: MCPBA / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C -> room temperature, 4.5 h

With pyridine; sulfuric acid; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00543a063

upstream raw materials:

diazomethane

(+/-)-isomarasmic acid

4,4-dimethyl-1-cyclopentene-1-carboxaldehyde

4,4-dimethylcyclopentene-1-carboxaldehyde diethyl acetal

Downstream raw materials:

(+/-)-marasmic acid