(R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate

Base Information

• Chemical Name: (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate
• CAS No.: 133715-24-9
• Molecular Formula: C₃₄H₃₃NO₅
• Molecular Weight: 535.64
• Mol file: 133715-24-9.mol

Synonyms:(R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate

Chemical Property of (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate

There total 9 articles about (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate 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:

(R)-2-cyclohexen-1-ol (3413-44-3) → (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate (133715-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1: o-nitrophenol / 9 h / 170 °C

2: 1N aq. NaOH / methanol / 12 h / Ambient temperature

3: 91.9 percent / SOCl₂ / benzene / 1.5 h / Heating

4: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C, 1 h

With sodium hydroxide; thionyl chloride; sodium hydride; 2-hydroxynitrobenzene; In methanol; benzene;

DOI:10.1016/0957-4166(96)00199-1

Reference yield:

(R)-(2-cyclohexen-1-yl)acetyl chloride (133775-35-6) + p-methoxybenzyl (E)-3-(4-benzyloxy-1 H-indol-3-yl)propenoate → (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate (133715-24-9)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C, 1 h;

DOI:10.1016/0957-4166(96)00199-1

Reference yield:

(1R,2R)-1-acetoxy-2-iodocyclohexane (144300-25-4) → (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate (133715-24-9)

Guidance literature:

Multi-step reaction with 6 steps

1: DBU / 120 °C

2: 86.9 percent / 1N aq. NaOH / methanol / Ambient temperature

3: o-nitrophenol / 9 h / 170 °C

4: 1N aq. NaOH / methanol / 12 h / Ambient temperature

5: 91.9 percent / SOCl₂ / benzene / 1.5 h / Heating

6: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C, 1 h

With sodium hydroxide; thionyl chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxynitrobenzene; In methanol; benzene;

DOI:10.1016/0957-4166(96)00199-1

upstream raw materials:

(R)-(2-cyclohexen-1-yl)acetyl chloride

(1R,2R)-1-acetoxy-2-iodocyclohexane

(1R, 2R)-2-(phenylthio)cyclohexyl acetate

(R)-2-cyclohexen-1-ol

Downstream raw materials:

((3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthen-11-yl)-carbamic acid benzyl ester

(3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide

<3aR-(3aα,12α,12aα,12bα)>-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-2(1H)-one hydrochloride