(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

Base Information

Chemical Name:(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal
CAS No.:252289-37-5
Molecular Formula:C₁₁H₁₆O
Molecular Weight:164.247
Hs Code.:

Synonyms:(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

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Chemical Property of (1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

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Technology Process of (1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

There total 15 articles about (1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal 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: 96.0%

: 252289-36-4
(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanenitrile

: 252289-37-5
(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at -65 - 20 ℃; for 3h;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 13834-16-7
(1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol

: 252289-37-5
(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

Guidance literature:: Multi-step reaction with 15 steps

1: 85 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

2: 65 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

5: 70 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

6: 93 percent / H₂O₂; NaOH / methanol / 0 °C

7: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 - 20 °C

8: 100 percent / Et₃N / tetrahydrofuran / 14 h / 0 - 20 °C

9: 90 percent / LiNEt₂ / tetrahydrofuran / 2 h / Heating

10: Et₃N / CH₂Cl₂ / 2 h / 0 °C

11: 63 percent / NaI; pyridine / acetone / 1 h / Heating

12: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 14 h / 0 - 20 °C

13: 75 percent / pyridine; DMAP / 3 h / 0 °C

14: 95 percent / dimethylsulfoxide / 2 h / 20 °C

15: 96 percent / DIBAH / diethyl ether; hexane / 3 h / -65 - 20 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; lithium diethylamide; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; sodium iodide; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination / 6: Epoxidation / 7: Reduction / 8: Substitution / 9: Rearrangement / 10: Acylation / 11: Elimination / 12: Hydrolysis / 13: Acylation / 14: Substitution / 15: Reduction;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 252289-34-2
(1'R,2S)-2-(4'-methylenecyclohex-2'-en-1'-yl)propan-1-ol

: 252289-37-5
(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / pyridine; DMAP / 3 h / 0 °C

2: 95 percent / dimethylsulfoxide / 2 h / 20 °C

3: 96 percent / DIBAH / diethyl ether; hexane / 3 h / -65 - 20 °C

With pyridine; dmap; diisobutylaluminium hydride; In diethyl ether; hexane; dimethyl sulfoxide; 1: Acylation / 2: Substitution / 3: Reduction;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T