(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

Base Information

Chemical Name:(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate
CAS No.:198022-62-7
Molecular Formula:C₂₆H₂₇NO₄
Molecular Weight:417.505
Hs Code.:

Synonyms:(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

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Chemical Property of (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

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Technology Process of (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

There total 10 articles about (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate 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:

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: (1R,2S)-2-Isocyanato-4-methylene-cyclopentanecarboxylic acid (E)-3-phenyl-allyl ester

: 198022-62-7
(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

Guidance literature:: In toluene; Heating;
DOI:10.1055/s-2003-36265

Reference yield:

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: (1R,2S)-2-Azidocarbonyl-4-methylene-cyclopentanecarboxylic acid (E)-3-phenyl-allyl ester

: 198022-62-7
(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

Guidance literature:: In toluene; Heating;
DOI:10.1016/S0960-894X(02)00958-7

Reference yield:

: 4534-68-3
1,2,3,4-butanetetracarboxylic acid

: 198022-62-7
(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: H₂SO₄ / toluene / 9 h / Heating

2.1: NaOMe / methanol / 1 h / 20 °C

3.1: aq. HCl / methanol / 20 - 57 °C

4.1: aq. HCl / 5 h / 100 °C

5.1: 1.72 kg / H₂SO₄ / 4 h / Heating

6.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

6.2: tetrahydrofuran / 2 h / -15 - 10 °C

7.1: 145 g / aq. KOH / tetrahydrofuran / 20 °C

8.1: 75 percent / (EtCO)2O / 8 h / 135 °C

9.1: 84 percent / (R)-(6-methoxyquinolin-4-yl)-(5-vinyl-1-azabicyclo[2.2.2]...; dihydroquinine / toluene / -15 °C

10.1: (PhO)2PON₃; Et₃N / toluene / 0.5 h / 90 °C

11.1: 62.0 g / toluene / Heating

With hydrogenchloride; potassium hydroxide; (R)-(6-methoxyquinolin-4-yl)-(5-vinyl-1-azabicyclo[2.2.2]..; sulfuric acid; diphenyl phosphoryl azide; potassium tert-butylate; sodium methylate; propionic acid anhydride; triethylamine; dihydroquinine; In tetrahydrofuran; methanol; toluene; 2.1: Dieckmann cyclization / 6.2: Wittig reaction / 10.1: Curtius rearrangement;
DOI:10.1055/s-2003-36265