ISO-ISOVELLERAL

Base Information

• Chemical Name: ISO-ISOVELLERAL
• CAS No.: 109956-89-0
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 109956-89-0.mol

Synonyms:Cycloprop[e]indene-1a,2(1H)-dicarboxaldehyde,3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethyl-, [1aR-(1aa,3aa,6aa,6ba)]-; Isoisovelleral

Chemical Property of ISO-ISOVELLERAL

Chemical Property:

• Vapor Pressure: 0.000273mmHg at 25°C
• Boiling Point: 322.8°Cat760mmHg
• Flash Point: 120.9°C
• PSA: 34.14000
• Density: 1.211g/cm³
• LogP: 2.77300

Purity/Quality:

ISO-ISOVELLERAL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ISO-ISOVELLERAL

There total 11 articles about ISO-ISOVELLERAL 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: 38.0%

(+)-isovelleral (37841-91-1) → iso-isovelleral (109956-89-0)

Guidance literature:

In toluene; at 200 ℃; for 11h;

DOI:10.1021/jo00040a020

Reference yield:

(4R,5R)-5-[(E)-2-(4,4-Dimethyl-cyclopent-1-enyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride (130543-23-6) → iso-isovelleral (109956-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether

2: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 22 deg C, 6 h, 2.) H₂O, 22 deg C, 0.5 h

3: 86 percent / dimethylaminopyridine, pyridine / CH₂Cl₂ / 1 h / -70 - 22 °C

4: 75 percent / 0.2 M H₂SO₄ / methanol; H₂O / 20 h / 22 °C

5: NaIO₄ / ethanol / 0.5 h / 22 °C

6: pyridine / 0.5 h / Heating

With pyridine; dmap; sodium hydroxide; sodium periodate; borane-THF; sulfuric acid; dihydrogen peroxide; In methanol; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1039/c39900000865

Reference yield:

(4,4-Dimethyl-cyclopent-1-enylmethyl)-triphenyl-phosphonium; bromide (130543-20-3) → iso-isovelleral (109956-89-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, 2 deg C, 2a.) -70 deg C, 15 min, 2b.) reflux, 2 h

2: 1-chloro-N,N,2-trimethylprop-1-enylamine / CH₂Cl₂ / 0.03 h / 22 °C

3: diethyl ether

4: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 22 deg C, 6 h, 2.) H₂O, 22 deg C, 0.5 h

5: 86 percent / dimethylaminopyridine, pyridine / CH₂Cl₂ / 1 h / -70 - 22 °C

6: 75 percent / 0.2 M H₂SO₄ / methanol; H₂O / 20 h / 22 °C

7: NaIO₄ / ethanol / 0.5 h / 22 °C

8: pyridine / 0.5 h / Heating

With pyridine; dmap; sodium hydroxide; sodium periodate; n-butyllithium; borane-THF; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; sulfuric acid; dihydrogen peroxide; In methanol; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1039/c39900000865

upstream raw materials:

(+)-isovelleral

Acetic acid (1aS,2S,3S,3aR,6aS,6bS)-1a,2-diformyl-5,5,6b-trimethyl-decahydro-cyclopropa[e]inden-3-yl ester

C₁₉H₃₀O₄

(4R,5R)-5-[(E)-2-(4,4-Dimethyl-cyclopent-1-enyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride

Downstream raw materials:

(+)-isovelleral

Refernces

• 1、 Hansson, Thomas,Bergman, Rolf,Sterner, Olov,Wickberg, Boerje. "The Mechanism of the Thermal Rearrangement of the Marasmane Sesquiterpene (+)-Isovelleral. Cyclopropane Ring Closure via an Intramolecular Ene Reaction". . p. 1260 - 1262. Retrieved 1990.