phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

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Chemical Name:phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate
CAS No.:718629-33-5
Molecular Formula:C₂₃H₁₉NO₃
Molecular Weight:357.409
Hs Code.:

Synonyms:phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

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Chemical Property of phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

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Technology Process of phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

There total 10 articles about phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate 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: 57.0%

: 718629-32-4
phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate

: 718629-33-5
phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate; With n-butyllithium; at -78 ℃;

With potassium carbonate; In methanol; at 0 ℃; Further stages.;
DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

: phenyl (2R)-4-[(R)-5-acetoxypent-1-yn-3-yl]-2-(trimethylsilyl)ethynyl-1,2-dihydroquinoline-1-carboxylate

: 718629-33-5
phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: With potassium carbonate; In methanol; at 0 - 20 ℃; optical yield given as %ee;
DOI:10.1002/ejoc.200901478

Reference yield:

: 213478-44-5
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propan-1-ol

: 718629-33-5
phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine

2.1: nBu₄NI / dimethylsulfoxide

3.1: DIBAL-H / -70 °C

3.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

4.1: 100 percent / pyridine

5.1: tetrahydrofuran / -78 °C

6.1: HF / acetonitrile; H₂O / 0 °C

7.1: (COCl)2; EtN(iPr)2; DMSO / CH₂Cl₂ / 14 h / -78 °C

8.1: 77 percent / PPh₃ / CH₂Cl₂ / -78 - -40 °C

9.1: n-BuLi / -78 °C

9.2: 57 percent / K₂CO₃ / methanol / 0 °C

With n-butyllithium; oxalyl dichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 7.1: Swern oxidation / 8.1: Corey-Fuchs reaction;
DOI:10.1016/j.tetlet.2004.04.029