Tonghaosu, (Z)-

Base Information

• Chemical Name: Tonghaosu, (Z)-
• CAS No.: 4575-53-5
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.237
• European Community (EC) Number: 853-475-9
• UNII: 07I4HKZ4B8
• Nikkaji Number: J414.343D
• Wikidata: Q27236314
• Mol file: 4575-53-5.mol

Synonyms:(Z)-Tonghaosu;Tonghaosu, (Z)-;cis-en Yne-dicycloether;UNII-07I4HKZ4B8;07I4HKZ4B8;4575-53-5;1,6-Dioxaspiro(4.4)non-3-ene, 2-(2,4-hexadiynylidene)-, (2Z)-;(Z)-2-(2,4-HEXADIYNYLIDENE)-1,6-DIOXASPIRO(4.4)NON-3-ENE;cis-En-yn-dicycloether;cis-ene-yne-Dicycloether;(Z)-ene-yne-Dicycloether;SCHEMBL3660562;WTRXKCNFPMTAJV-GHXNOFRVSA-N;EN300-21996782;Q27236314;2-(2,4-hexadiyliden)-1,6-dioxaspiro[4,4] non-3-ene;CIS-EN-YN-DICYCLOETHER (CONSTITUENT OF CHAMOMILE);2-[(Z)-2,4-Hexadiynylidene]-1,6-dioxaspiro[4.4]non-3-ene;CIS-EN-YN-DICYCLOETHER (CONSTITUENT OF CHAMOMILE) [DSC];(Z)-2-(Hexa-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene;(2Z)-2-(2,4-HEXADIYNYLIDENE)-1,6-DIOXASPIRO(4,4)NON-3-ENE;(2Z)-2-(HEXA-2,4-DIYN-1-YLIDENE)-1,6-DIOXASPIRO[4.4]NON-3-ENE

Chemical Property of Tonghaosu, (Z)-

Chemical Property:

• PSA: 18.46000
• LogP: 1.99010
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 444

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC#CC=C1C=CC2(O1)CCCO2
• Isomeric SMILES: CC#CC#C/C=C\1/C=CC2(O1)CCCO2

Technology Process of Tonghaosu, (Z)-

There total 12 articles about Tonghaosu, (Z)- 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:

1-[5-(3-Hydroxy-propyl)-furan-2-yl]-hexa-2,4-diyn-1-ol (170577-93-2) → (E)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro[4.4]non-3-ene (4575-53-5,16863-61-9,50257-98-2,85317-91-5,85799-13-9,85799-15-1,112653-03-9,112653-04-0) + (Z)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro[4.4]non-3-ene (4575-53-5,16863-61-9,50257-98-2,85317-91-5,85799-13-9,85799-15-1,112653-03-9,112653-04-0)

Guidance literature:

With copper(II) sulfate; In toluene; at 70 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(98)00732-7

Reference yield:

1-[5-(3-Hydroxy-propyl)-furan-2-yl]-hexa-2,4-diyn-1-ol (170577-93-2) → (E)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro[4.4]non-3-ene (4575-53-5,16863-61-9,50257-98-2,85317-91-5,85799-13-9,85799-15-1,112653-03-9,112653-04-0) + (Z)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro[4.4]non-3-ene (4575-53-5,16863-61-9,50257-98-2,85317-91-5,85799-13-9,85799-15-1,112653-03-9,112653-04-0)

Guidance literature:

With copper(II) sulfate; In toluene; at 70 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(98)00732-7

Reference yield:

3-furan-2-yl-propan-1-ol (26908-23-6) → (E)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro[4.4]non-3-ene (4575-53-5,16863-61-9,50257-98-2,85317-91-5,85799-13-9,85799-15-1,112653-03-9,112653-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / DMAP / pyridine / 12 h / Ambient temperature

2: 91 percent / POCl₃ / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) n-BuLi, TMEDA / 1.) THF, hexane, -78 deg C to rt, 2.) THF, hexane, 0 deg C to rt

4: 92 percent / KHCO₃ / methanol; H₂O / 12 h / 40 °C

5: CuSO₄*5H₂O / toluene / 3 h / 70 °C

With dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium hydrogencarbonate; copper(II) sulfate; trichlorophosphate; In pyridine; methanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(98)00732-7

upstream raw materials:

1-[5-(3-Hydroxy-propyl)-furan-2-yl]-hexa-2,4-diyn-1-ol

3-furan-2-yl-propan-1-ol

3-(furan-2-yl)propyl acetate

5-(3-acetoxypropyl)-2-furaldehyde

Refernces

• 1、 Bohlmann,Florentz. "Polyacetylene compounds, XCVI. On the biogenesis of spiroketalenoletherpolyine". . p. 990 - 994. Retrieved 2007/10/09.