Dehydroheliotridine

Base Information

• Chemical Name: Dehydroheliotridine
• CAS No.: 26400-24-8
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.181
• Hs Code.: 2933990090
• NSC Number: 116336
• UNII: EGL727L56R
• DSSTox Substance ID: DTXSID00181000
• Nikkaji Number: J369.845I
• Wikidata: Q27277173
• ChEMBL ID: CHEMBL1999592
• Mol file: 26400-24-8.mol

Synonyms:6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine;dehydro-retronecine;dehydroheliotridine;dehydroretro-necine;dehydroretronecine;dehydroretronecine, (R)-isomer;dehydroretronecine, (S)-isomer

Chemical Property of Dehydroheliotridine

Chemical Property:

• Vapor Pressure: 7.54E-06mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• Boiling Point: 361.2°Cat760mmHg
• Flash Point: 172.3°C
• PSA: 45.39000
• Density: 1.39g/cm³
• LogP: 0.41750
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 153.078978594
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

DEHYDROHELIOTRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrroles
• Canonical SMILES: C1CN2C=CC(=C2C1O)CO
• Isomeric SMILES: C1CN2C=CC(=C2[C@H]1O)CO

Technology Process of Dehydroheliotridine

There total 5 articles about Dehydroheliotridine 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:

7α-Hydroxy-6,7-dihydro-pyrrolizin-1-carbaldehyd (28379-57-9) → (+)-dehydroheliotridine (26400-24-8,31470-63-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.333333h; Yield given;

DOI:10.1021/jo00223a002

Reference yield:

1-aza-4-(1,3-dithian-2-ylidene)-6(S)-(acetyloxy)bicyclo<3.3.0>octan-8-one (85319-62-6) → (+)-dehydroheliotridine (26400-24-8,31470-63-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 80 percent / LDA / methanol

3: CaCO₃, HgCl₂ / acetonitrile; H₂O / 50 °C

4: NaBH₄ / methanol / 0.33 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; calcium carbonate; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1021/jo00223a002

Reference yield:

(1S,7aR)-7-[1,3]Dithian-2-yl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol (98634-58-3) → (+)-dehydroheliotridine (26400-24-8,31470-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: CaCO₃, HgCl₂ / acetonitrile; H₂O / 50 °C

2: NaBH₄ / methanol / 0.33 h

With sodium tetrahydroborate; calcium carbonate; mercury dichloride; In methanol; water; acetonitrile;

DOI:10.1021/jo00223a002

upstream raw materials:

7α-Hydroxy-6,7-dihydro-pyrrolizin-1-carbaldehyd

1-aza-4-(1,3-dithian-2-ylidene)-6(S)-(acetyloxy)bicyclo<3.3.0>octan-8-one

(1S,7aR)-7-[1,3]Dithian-2-yl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol

5(R)-1-aza-4-(1,3-dithian-2-ylidene)-6(S)-hydroxybicyclo<3.3.0>octane

Refernces