Diploptene

Base Information

• Chemical Name: Diploptene
• CAS No.: 1615-91-4
• Molecular Formula: C₃₀H₅₀
• Molecular Weight: 410.727
• DSSTox Substance ID: DTXSID30936540
• Nikkaji Number: J7.532I
• Wikidata: Q14124950
• Metabolomics Workbench ID: 53141
• ChEMBL ID: CHEMBL455613
• Mol file: 1615-91-4.mol

Synonyms:22(29)-hopene;diploptene;hopene

Chemical Property of Diploptene

Chemical Property:

• Vapor Pressure: 3.67E-08mmHg at 25°C
• Melting Point: 151 °C(Solv: acetone (67-64-1); methanol (67-56-1))
• Boiling Point: 458.7°Cat760mmHg
• Flash Point: 231.1°C
• PSA: 0.00000
• Density: 0.934g/cm³
• LogP: 9.05400
• Storage Temp.: −20°C
• XLogP3: 11.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 410.391251595
• Heavy Atom Count: 30
• Complexity: 730

Purity/Quality:

99% ^*data from raw suppliers

Hop-22(29)-ene solution 0.1mg/mL in isooctane, analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 60-61-62-33-29-16-9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1CCC3(C2CCC4C3(CCC5C4(CCCC5(C)C)C)C)C)C
• Isomeric SMILES: CC(=C)[C@H]1CC[C@]2([C@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCCC5(C)C)C)C)C)C

Technology Process of Diploptene

There total 26 articles about Diploptene 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: 55.0%

(4S,5R)-4-Benzyloxymethyl-2,2-dimethyl-5-(R)-oxiranyl-[1,3]dioxolane (863398-02-1) + (3S,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-3-(2-Bromo-1-methyl-ethyl)-5a,5b,8,8,11a,13b-hexamethyl-icosahydro-cyclopenta[a]chrysene → (R)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-((3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-pentan-1-ol + hopane (471-62-5,1176-44-9,13849-96-2,33281-23-1,50894-70-7) + diploptene (1615-91-4,1812-64-2,33323-60-3,33323-61-4,43206-60-6)

Guidance literature:

With lithium di-tert-butylbiphenylide; thien-2-yl(cyano)copper lithium; naphthalen-1-yl-lithium; In tetrahydrofuran; at -30 - 20 ℃;

DOI:10.1039/b504558d

Reference yield: 40.0%

30-iodohopane + (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → C39H66O5 + hopane (471-62-5,1176-44-9,13849-96-2,33281-23-1,50894-70-7) + diploptene (1615-91-4,1812-64-2,33323-60-3,33323-61-4,43206-60-6)

Guidance literature:

30-iodohopane; With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; In tetrahydrofuran;

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde; In tetrahydrofuran; Further stages.;

DOI:10.1002/chem.200600659

Reference yield: 21.0%

hopan-22-ol (1721-59-1) → diploptene (1615-91-4,1812-64-2,33323-60-3,33323-61-4,43206-60-6)

Guidance literature:

With acetic anhydride; potassium carbonate; for 3h; Reflux;

DOI:10.1002/anie.201911584

upstream raw materials:

3-oxo-hop-22⁽²⁹⁾-ene

hopan-22-ol

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(4S,5R)-4-Benzyloxymethyl-2,2-dimethyl-5-(R)-oxiranyl-[1,3]dioxolane

Downstream raw materials:

dryocrassol

hopyltriphenylphosphonium iodide