2-[(1R,3E,7Z,11Z)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]prop-2-enal

Base Information

• Chemical Name: 2-[(1R,3E,7Z,11Z)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]prop-2-enal
• CAS No.: 118607-64-0
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.458
• Mol file: 118607-64-0.mol

Synonyms:3,7,11-Cyclotetradecatriene-1-acetaldehyde,4,8,12-trimethyl-a-methylene-,[R-(E,E,E)]-; (+)-Sinularial A; Sinularial A

Chemical Property of 2-[(1R,3E,7Z,11Z)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]prop-2-enal

Chemical Property:

• Vapor Pressure: 4.37E-07mmHg at 25°C
• Boiling Point: 414.7°Cat760mmHg
• Flash Point: 196.1°C
• Density: 0.881g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(1R,3E,7Z,11Z)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]prop-2-enal

There total 17 articles about 2-[(1R,3E,7Z,11Z)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]prop-2-enal 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: 92.0%

(+)-sinulariol-D (118583-93-0) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal (118607-64-0)

Guidance literature:

With manganese(IV) oxide; In hexane; at 15 ℃; for 12h;

DOI:10.1016/S0957-4166(99)00194-9

Reference yield:

2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propanoic acid (118583-94-1) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal (118607-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 6.7 mg / LiAlH₄ / tetrahydrofuran

2: 55.5 mg / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 6 h / Ambient temperature

With lithium aluminium tetrahydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

Reference yield:

trans-geranyl bromide (6138-90-5) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal (118607-64-0)

Guidance literature:

Multi-step reaction with 12 steps

1: dimethylformamide / 24 h / Ambient temperature

2: 78 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 25 h / 20 °C

3: 1.) Ti(OiPr)4, CaH₂, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, toluene, -40 deg C, 5 h

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h

5: 78 percent / Li, EtNH₂ / tetrahydrofuran / 4 h / -78 °C

6: 1.) Ph₃P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h

7: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C

8: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C

9: Bu₄N₊F_- / tetrahydrofuran / 24 h / 15 °C

10: 70 percent / Li, EtNH₂ / tetrahydrofuran / 3.5 h / -78 °C

11: 49 percent / SOCl₂, pyridine / 3 h / 15 °C

12: 92 percent / MnO₂ / hexane / 12 h / 15 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; N-chloro-succinimide; selenium(IV) oxide; thionyl chloride; calcium hydride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; lithium; ethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(99)00194-9

upstream raw materials:

(+)-sinulariol-D

trans-geranyl bromide

Geraniol

3,7-dimethyl-2E,6-octadien-1-yl acetate

Downstream raw materials:

2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propanoic acid

(+)-sinulariol-D

Refernces

• 1、 Kobayashi, Masaru,Hamaguchi, Takuya. "Marine Terpenes and Terpenoids. VI. Isolation of Several Plausible Precursors of Marine Cembranolides, from the Soft Coral, Sinularia mayi". . p. 3780 - 3786. Retrieved 2007/10/02.