(2R)-2-but-3-enyloxirane

Base Information

• Chemical Name: (2R)-2-but-3-enyloxirane
• CAS No.: 137688-20-1
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• European Community (EC) Number: 604-033-7
• DSSTox Substance ID: DTXSID501309151
• Nikkaji Number: J951.341H
• Mol file: 137688-20-1.mol

Synonyms:137688-20-1;(2R)-2-but-3-enyloxirane;(2R)-2-(BUT-3-EN-1-YL)OXIRANE;(R)-(+)-1,2-EPOXY-5-HEXENE;(+)-1,2-epoxyhex-5-ene;(2R)-2-(3-Buten-1-yl)oxirane;Oxirane, 2-(3-buten-1-yl)-, (2R)-;(r)-2-(but-3-enyl)oxirane;(R)-2-(but-3-en-1-yl)oxirane;2alpha-(3-Butenyl)oxirane;(R)-1,2-epoxy-5-hexene;MUUOUUYKIVSIAR-ZCFIWIBFSA-N;DTXSID501309151;EN300-746561;A1-01450;J-800396

Chemical Property of (2R)-2-but-3-enyloxirane

Chemical Property:

• Boiling Point: 120 °C at 760 mmHg
• Flash Point: 15.6 °C
• PSA: 12.53000
• Density: 0.892 g/cm³
• LogP: 1.35140
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 68.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-2-(but-3-en-1-yl)oxirane 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCCC1CO1
• Isomeric SMILES: C=CCC[C@@H]1CO1

Technology Process of (2R)-2-but-3-enyloxirane

There total 13 articles about (2R)-2-but-3-enyloxirane 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: 86.0%

1,2-epoxy-5-hexene (10353-53-4) → (R)-2-(but-3-en-1-yl)oxirane (137688-20-1)

Guidance literature:

With (R,R) Co(salen); water;

Reference yield: 44.0%

1,2-epoxy-5-hexene (10353-53-4) → (S)-hex-5-ene-1,2-diol (127102-61-8) + (R)-2-(but-3-en-1-yl)oxirane (137688-20-1)

Guidance literature:

With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 10h;

DOI:10.1021/ja016737l

Reference yield: 44.0%

1,2-epoxy-5-hexene (10353-53-4) → (S)-hex-5-ene-1,2-diol (127102-61-8) + (R)-2-(but-3-en-1-yl)oxirane (137688-20-1) + (-)-(S)-2-(but-3-enyl)oxirane (137688-21-2)

Guidance literature:

With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja016737l

upstream raw materials:

1,2-epoxy-5-hexene

1,5-Hexadien

(R)-1,2-dihydroxy-5-hexene

Downstream raw materials:

(2R)-hex-5-en-2-ol

amphidinolide C

methyl 2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}-5-(trifluoromethyl)pyridine-4-carboxylate

methyl 2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-4-carboxylate

Refernces

• 1、 Menke, Markus,Peram, Pardha Saradhi,Starnberger, Iris,H?dl, Walter,Jongsma, Gregory F. M.,Blackburn, David C.,R?del, Mark-Oliver,Vences, Miguel,Schulz, Stefan. "Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris". supporting information. p. 2731 - 2738. Retrieved 2017/01/09.
• 2、 Austad, Brian C.,Benayoud, Farid,Calkins, Trevor L.,Campagna, Silvio,Chase, Charles E.,Choi, Hyeong-Wook,Christ, William,Costanzo, Robert,Cutter, James,Endo, Atsushi,Fang, Francis G.,Hu, Yongbo,Lewis, Bryan M.,Lewis, Michael D.,McKenna, Shawn,Noland, Thomas A.,Orr, John D.,Pesant, Marc,Schnaderbeck, Matthew J.,Wilkie, Gordon D.,Abe, Taichi,Asai, Naoki,Asai, Yumi,Kayano, Akio,Kimoto, Yuichi,Komatsu, Yuki,Kubota, Manabu,Kuroda, Hirofumi,Mizuno, Masanori,Nakamura, Taiju,Omae, Takao,Ozeki, Naoki,Suzuki, Taeko,Takigawa, Teiji,Watanabe, Tomohiro,Yoshizawa, Kazuhiro. "Process development of halaven: Synthesis of the C14-C35 fragment via iterative nozaki-hiyama-kishi reaction-williamson ether cyclization". . p. 327 - 332. Retrieved 2013/04/10.