(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Base Information

• Chemical Name: (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde
• CAS No.: 217448-26-5
• Molecular Formula: C₂₇H₃₀N₂O
• Molecular Weight: 398.548
• Mol file: 217448-26-5.mol

Synonyms:(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Chemical Property of (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

There total 16 articles about (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 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: 95.0%

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (217448-33-4) → (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (217448-26-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1016/S0040-4039(98)01788-2

Reference yield: 85.0%

(6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-25-4) → (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (217448-26-5)

Guidance literature:

With methanol; 18-crown-6 ether; potassium hydride; In 1,4-dioxane;

DOI:10.1021/jo030116o

Reference yield:

(6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole (197143-13-8) → (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (217448-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: KOH / H₂O / 20 °C

1.3: 87 percent / LiClO₄ / dioxane / 24 h / Heating

2.1: 90 percent / Li; biphenyl; BaI / tetrahydrofuran / -78 °C

3.1: KH; 18-crown-6 / dioxane / 14 h / 100 °C

With 18-crown-6 ether; biphenyl; barium(II) iodide; lithium; potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; 3.1: Oxy-anion Cope rearrangement;

DOI:10.1021/ol000331g

upstream raw materials:

(6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

(E)-1-bromo-2-pentene

(6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole

Downstream raw materials:

(6S,10S)-8-(1'-ethyl-2'-propenyl)-9-(2',5'-dioxacyclopentanyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole

(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

C₂₇H₃₀N₂O

(6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane