exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol

Base Information

• Chemical Name: exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol
• CAS No.: 461703-09-3
• Molecular Formula: C₂₇H₂₂O₂
• Molecular Weight: 378.47

Synonyms:exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol

Chemical Property of exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol

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Technology Process of exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol

There total 1 articles about exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-endo-8,endo-11-diol 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: 62.0%

pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (2958-72-7) + phenylacetylene (536-74-3) → exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecane-endo-8,endo-11-diol (461703-09-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 60 ℃; for 24h;

DOI:10.1023/A:1014311703618

Reference yield: 81.0%

exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecane-endo-8,endo-11-diol (461703-09-3) → 3,5-bis(2'-phenylethynyl)hexacyclo[5.4.1.0.02,6.03,10.05,9]dodecane

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 4h; Heating;

DOI:10.1023/A:1014311703618

Reference yield:

exo-8,exo-11-bis(2'-phenylethynyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecane-endo-8,endo-11-diol (461703-09-3) → C27H20O5

Guidance literature:

Multi-step reaction with 2 steps

1.1: 81 percent / TsOH / benzene / 4 h / Heating

2.1: KMnO₄; benzyltri(n-butyl)ammonium bromide; AcOH / CH₂Cl₂ / 4 h / Heating

2.2: 67 percent / Na₂S₂O₅; 10 percent aq. H₂SO₄ / CH₂Cl₂ / 0.33 h / 5 °C

With potassium permanganate; benzyl tri-n-butylammonium bromide; toluene-4-sulfonic acid; acetic acid; In dichloromethane; benzene;

DOI:10.1023/A:1014311703618

upstream raw materials:

pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-8,11-dione

phenylacetylene

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