6-[(Z)-1-Butenyl]-1,4-cycloheptadiene

Base Information

• Chemical Name: 6-[(Z)-1-Butenyl]-1,4-cycloheptadiene
• CAS No.: 33156-92-2
• Molecular Formula: C11H16
• Molecular Weight: 148.2447
• Nikkaji Number: J591.450G
• Wikipedia: Ectocarpene
• Metabolomics Workbench ID: 168585
• Mol file: 33156-92-2.mol

Synonyms:1-(1-butenyl)-2,5-cycloheptadiene;ectocarpene

Chemical Property of 6-[(Z)-1-Butenyl]-1,4-cycloheptadiene

Chemical Property:

• Vapor Pressure: 0.325mmHg at 25°C
• Boiling Point: 207.4°Cat760mmHg
• Flash Point: 63.5°C
• Density: 0.908g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 148.125200510
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC=CC1CC=CCC=C1
• Isomeric SMILES: CC/C=C\C1CC=CCC=C1

Technology Process of 6-[(Z)-1-Butenyl]-1,4-cycloheptadiene

There total 11 articles about 6-[(Z)-1-Butenyl]-1,4-cycloheptadiene 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:

Acetic acid (1S,2R)-2-((E)-2-iodo-vinyl)-cyclopropylmethyl ester → Ectocarpen (33156-92-2,52589-18-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) CuBr*SMe₂, 2.) ZnBr₂, 3.) Pd(PPh₃)2 / 1.) Et₂O, -40 deg C, 30 min, 2.) THF, -25 deg C, 20 min, 3.) Et₂O, THF, pyrrolidine, 2 h

2: 99 percent / K₂CO₃ / methanol; H₂O / 3 h / Ambient temperature

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 25 min, 2.) -60 deg C to room temperature

4: 1.) NaH/DMSO / 1.) pentane, room temperature, 2.) 5 deg C, 3 min

5: Ambient temperature; E_a, ln A; Cope rearrangement of thermolabile bis-alkenylcyclopropanes

With oxalyl dichloride; copper(I) bromide dimethylsulfide complex; bis(triphenylphosphine)palladium⁽⁰⁾; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; zinc dibromide; In methanol; water;

DOI:10.1016/S0040-4020(97)00886-7

Reference yield:

Acetic acid (1S,2S)-((1E,3Z)-2-hexa-1,3-dienyl)-cyclopropylmethyl ester (197773-73-2) → Ectocarpen (33156-92-2,52589-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / K₂CO₃ / methanol; H₂O / 3 h / Ambient temperature

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 25 min, 2.) -60 deg C to room temperature

3: 1.) NaH/DMSO / 1.) pentane, room temperature, 2.) 5 deg C, 3 min

4: Ambient temperature; E_a, ln A; Cope rearrangement of thermolabile bis-alkenylcyclopropanes

With oxalyl dichloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In methanol; water;

DOI:10.1016/S0040-4020(97)00886-7

Reference yield:

(1S,2S)-((1E,3Z)-2-Hexa-1,3-dienyl)-cyclopropanecarbaldehyde (197579-08-1) → Ectocarpen (33156-92-2,52589-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH/DMSO / 1.) pentane, room temperature, 2.) 5 deg C, 3 min

2: Ambient temperature; E_a, ln A; Cope rearrangement of thermolabile bis-alkenylcyclopropanes

With sodium hydride; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(97)00886-7

upstream raw materials:

all cis-5,8,11,14,17-eicosapentaenoic acid

n-propyltriphenylphosphonium bromide

Dictyopteren B 8

(1S,2R)-1-((1E,3Z)-Hexa-1,3-dienyl)-2-vinyl-cyclopropane

Refernces

• 1、 Stratmann, Klemens,Boland, Wilhelm,Mueller, Dieter G.. "Pheromone mariner Braunalgen; ein neuer Zweig des Eicosanoidstoffwechsels". . p. 1261 - 1263. Retrieved 2007/10/02.
• 2、 Kajiwara, Tadahiko,Sasaki, Yasuhi,Kimura, Fumiko,Hatanaka, Akikazu. "Stereoselctive Synthesis of Ectocarpene and its Antipode via Microbiological Asymmetric Hydrolysis". . p. 1461 - 1466. Retrieved 2007/10/02.