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:

hopyltriphenylphosphonium iodide

dryocrassol

Refernces

• 1、 Morelli,I.,Marsili,A.. "-". . p. 567 - 570. Retrieved 1970.
• 2、 Seitz, Miriam,Klebensberger, Janosch,Siebenhaller, Sascha,Hauer, Bernhard,Breuer, Michael,Siedenburg, Gabriele,Jendrossek, Dieter. "Substrate specificity of a novel squalene-hopene cyclase from Zymomonas mobilis". . p. 72 - 77,6. Retrieved 2012.
• 3、 Sato, Tsutomu,Abe, Takamasa,Hoshino, Tsutomu. "On the cyclization mechanism of squalene: A ring expansion process of the five-membered D-ring intermediate". . p. 2617 - 2618. Retrieved 1998.
• 4、 Pale-Grosdemange, Catherine,Merkofer, Thorsten,Rohmer, Michel,Poralla, Karl. "Production of bicyclic and tricyclic triterpenes by mutated squalene- hopene cyclase". . p. 6009 - 6012. Retrieved 1999.
• 5、 Hoshino, Tsutomu,Abe, Takamasa,Kouda, Masanori. "Unnatural natural triterpenes produced by altering isoleucine into alanine at position 261 in hopene synthase and the importance of having the appropriate bulk size at this position for directing the stereochemical destiny during the polycyclization cascade". . p. 441 - 442. Retrieved 2000.
• 6、 Syren, Per-Olof,Hammer, Stephan C.,Claasen, Birgit,Hauer, Bernhard. "Entropy is key to the formation of pentacyclic terpenoids by enzyme-catalyzed polycyclization". . p. 4845 - 4849. Retrieved 2014.
• 7、 Ideno, Natsumi,Umeyama, Shikou,Watanabe, Takashi,Nakajima, Mami,Sato, Tsutomu,Hoshino, Tsutomu. "Alicyclobacillus acidocaldarius Squalene-Hopene Cyclase: The Critical Role of Steric Bulk at Ala306 and the First Enzymatic Synthesis of Epoxydammarane from 2,3-Oxidosqualene". . p. 1873 - 1886. Retrieved 2018/08/01.