trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one

Base Information

• Chemical Name: trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one
• CAS No.: 97974-79-3
• Molecular Formula: C₃₄H₃₇I₂NO₄
• Molecular Weight: 777.481
• Mol file: 97974-79-3.mol

Synonyms:

Chemical Property of trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one

There total 8 articles about trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one 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: 81.0%

3-iodo-4-methoxybenzaldehyde (2314-37-6) + (4α,6α,8α,9aα)-(+/-)--3-(dimethylphosphinyl)-2-propanone (97974-78-2) → trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one (97974-79-3,110454-04-1)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1021/jo00219a061

Reference yield:

benzyl bromide (100-39-0) → trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one (97974-79-3,110454-04-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 36 h

2: 96 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / toluene / 0.17 h / 105 °C

3: 2.) triphenylphosphine, 1,4-diazabicyclo<2.2.2>octane / 1.) chloroform, RT, 24 h, 2.) chloroform, reflux, 1 h

4: 88 percent / sodium cyanoborohydride, HCl / methanol; tetrahydrofuran / 0.17 h / Ambient temperature

5: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 75 min

6: 1.) NaH / 1.) dimethoxyethane, RT, 1 h, 2.) dimethoxyethane, RT, 6 h

With Lawessons reagent; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; n-butyllithium; sodium hydride; sodium cyanoborohydride; triphenylphosphine; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/jo00230a003

Reference yield:

(6α,8α,9aα)-(+/-)-octahydro-6-(3-iodo-4-methoxyphenyl)-8-(phenylmethoxy)-4H-quinolizin-4-thione (97974-74-8) → trans-(4α,6α,8α,9aα)-(+/-)-4--1-(3-iodo-4-methoxyphenyl)-1-buten-3-one (97974-79-3,110454-04-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) triphenylphosphine, 1,4-diazabicyclo<2.2.2>octane / 1.) chloroform, RT, 24 h, 2.) chloroform, reflux, 1 h

2: 88 percent / sodium cyanoborohydride, HCl / methanol; tetrahydrofuran / 0.17 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 75 min

4: 1.) NaH / 1.) dimethoxyethane, RT, 1 h, 2.) dimethoxyethane, RT, 6 h

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; n-butyllithium; sodium hydride; sodium cyanoborohydride; triphenylphosphine; In tetrahydrofuran; methanol;

DOI:10.1021/jo00230a003

upstream raw materials:

3-iodo-4-methoxybenzaldehyde

(4α,6α,8α,9aα)-(+/-)--3-(dimethylphosphinyl)-2-propanone

benzyl bromide

(6α,8α,9aα)-(+/-)-octahydro-6-(3-iodo-4-methoxyphenyl)-8-(phenylmethoxy)-4H-quinolizin-4-thione

Downstream raw materials:

(+/-)-lythrancepine II

trans-<4α(S*),6α,8α,9aα>-(+/-)-octahydro-6-(3-iodo-4-methoxyphenyl)-α-<2-(3-iodo-4-methoxyphenyl)ethyl>-8-(phenylmethoxy)-2H-quinolizine-4-ethanol

(+/-)-3-O-benzyllythrancepine II

trans-<4α(S*),6α,8α,9aα>-(+/-)-octahydro-6-(3-iodo-4-methoxyphenyl)-α-<2-(3-iodo-4-methoxyphenyl)ethyl>-8-(phenylmethoxy)-2H-quinolizine-4-ethyl acetate