Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)-

Base Information

• Chemical Name: Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)-
• CAS No.: 25047-20-5
• Molecular Formula: C₁₁H₁₈
• Molecular Weight: 150.264
• Mol file: 25047-20-5.mol

Synonyms:Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)-

Chemical Property of Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)-

Chemical Property:

• Vapor Pressure: 1.37mmHg at 25°C
• Boiling Point: 177.9°Cat760mmHg
• Flash Point: 50.1°C
• Density: 0.885g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 150.140850574
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CCC1(CC1)C=C
• Isomeric SMILES: CCC/C=C/CC1(CC1)C=C

Technology Process of Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)-

There total 57 articles about Cyclopropane, 1-ethenyl-2-(1E)-1-hexen-1-yl-, (1S,2S)- 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: 85.0%

methyl-triphenylphosphonium iodide (2065-66-9) + (1S,2R)-2-(hex-1-enyl)cyclopropanecarbaldehyde → (1S,2R)-1-(hex-1-en-1-yl)-2-vinylcyclopropane (22822-99-7,22823-03-6,24519-26-4,25047-20-5,35501-91-8,50265-47-9,50265-49-1,53956-87-9,53956-88-0,53956-89-1,77210-40-3,99438-15-0,99438-16-1,106137-59-1,106137-61-5,133576-11-1)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 0.0833333h;

(1S,2R)-2-(hex-1-enyl)cyclopropanecarbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

DOI:10.1246/bcsj.73.409

Reference yield: 84.0%

C18H26N2O2S → 1S,2R-Dictyopterene C (22822-99-7,22823-03-6,24519-26-4,25047-20-5,35501-91-8,50265-47-9,50265-49-1,53956-87-9,53956-88-0,53956-89-1,77210-40-3,99438-15-0,99438-16-1,106137-59-1,106137-61-5,133576-11-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85604-0

Reference yield:

(5Z)-1,5-undecadien-3-ol (56722-23-7) → (+/-)-dictyopterene A (22822-99-7,22823-03-6,24519-26-4,25047-20-5,35501-91-8,50265-47-9,50265-49-1,53956-87-9,53956-88-0,53956-89-1,77210-40-3,99438-15-0,99438-16-1,106137-59-1,106137-61-5,133576-11-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 41 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

2: 42 percent / toluene / 0.25 h / 0 °C

3: 92 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4: pyridine / 1 h / 0 °C

5: 64 percent / CH₃COOK / acetone; H₂O / 20 h / 80 °C

6: H₃COOCN(-)SO₂N(+)(C₂H₅)3, NaH / 1,2-dimethoxy-ethane / 17 h / 20 - 80 °C

7: 1) CF₃SO₃CH₂COOC₂H₅, 2) DBU / 1) CH₃CN, room temp., 20 h, 2) DMF, 50 deg C, 3 h

With sodium tetrahydroborate; Burgess Reagent; ethoxycarbonylmethyl trifluoromethanesulfonate; potassium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; toluene;

DOI:10.1016/0040-4039(80)80163-8

upstream raw materials:

pentylidenetriphenylphosphorane

(Z)-(2S)-1,2-epoxy-6-(trimethylsilyl)-4-hexene

methyl-triphenylphosphonium iodide

(1S,2R)-2-(tert-butyldimethylsilanyloxymethyl)cyclopropanecarbaldehyde

Downstream raw materials:

R-(-)-Dictyopterene C'

Refernces

• 1、 Erickson, Lucas W.,Lucas, Erika L.,Tollefson, Emily J.,Jarvo, Elizabeth R.. "Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes". supporting information. p. 14006 - 14011. Retrieved 2016/11/06.
• 2、 Hohn, Erwin,Pale?ek, Ji?í,Pietruszka, J?rg. "Synthesis of dictyopterene A". scheme or table. p. 971 - 974. Retrieved 2009/04/04.