(+/-)-hippodamine

Base Information

• Chemical Name: (+/-)-hippodamine
• CAS No.: 59685-36-8
• Molecular Formula: C₁₃H₂₃N
• Molecular Weight: 193.332
• Mol file: 59685-36-8.mol

Synonyms:

Chemical Property of (+/-)-hippodamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-hippodamine

There total 40 articles about (+/-)-hippodamine 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: 37.0%

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6) + (+/-)-hippodamine (59685-36-8)

Guidance literature:

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine; With mesitylene sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1h;

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 48h; normal pressure;

DOI:10.1039/b413052a

Reference yield: 37.0%

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6) + (+/-)-hippodamine (59685-36-8)

Guidance literature:

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine; With mesitylene sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1h;

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 48h; normal pressure;

DOI:10.1039/b413052a

Reference yield:

2-[1-(4,5-dihydroxy-pentyl)-5,6-dihydroxy-hexyl]-isoindole-1,3-dione → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium periodate / tetrahydrofuran; 2-methyl-propan-2-ol / 20 h / 20 °C

2.1: NaH / tetrahydrofuran / 2 h / 20 °C

2.2: 9.76 g / tetrahydrofuran / 48 h / 20 °C

3.1: 66.9 percent / aq. NaBH₄ / propan-2-ol / 24 h / 20 °C

4.1: 4.38 g / glacial acetic acid / propan-2-ol; acetone / 24 h / Heating

5.1: t-BuOK; Li / benzene / 19 h / Heating

5.2: HCl / CHCl₃; diethyl ether / 1 h / 20 °C

5.3: 0.764 g / aq. LiCl / dimethylformamide / 4 h / Heating

6.1: 61.2 percent / toluene; diethyl ether / 5 h / 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: tetrahydrofuran; hexane / 3 h / -78 - 20 °C

7.3: tetrahydrofuran; hexane / 20 °C

8.1: tri-n-butyltin hydride; AIBN / toluene / 4 h / Heating

With sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; lithium; sodium hydride; acetic acid; In tetrahydrofuran; diethyl ether; hexane; isopropyl alcohol; acetone; toluene; tert-butyl alcohol; benzene; 2.1: Wadsworth-Emmons reaction / 5.1: Dieckmann condensation;

DOI:10.1039/b413052a

upstream raw materials:

(2α,3aα,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one

7-(2'-hydroxymethyl-benzoylamino)-trideca-2,11-dienedioic acid diethyl ester

6-hydroxy-1,10-undecadiene

5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-nonanedial