Merulidial

Base Information

• Chemical Name: Merulidial
• CAS No.: 68053-32-7
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• UNII: 08Y2276EUV
• DSSTox Substance ID: DTXSID801034325
• Nikkaji Number: J261.823K
• Wikidata: Q27896572
• Metabolomics Workbench ID: 28399
• Mol file: 68053-32-7.mol

Synonyms:merulidial

Chemical Property of Merulidial

Chemical Property:

• Vapor Pressure: 2.62E-07mmHg at 25°C
• Boiling Point: 379.2°Cat760mmHg
• Flash Point: 197.3°C
• PSA: 54.37000
• Density: 1.19g/cm³
• LogP: 1.88790
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 476

Purity/Quality:

MERULIDIAL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C(C3(CC3(C(=C2C1)C=O)C=O)C)O)C
• Isomeric SMILES: C[C@@]12C[C@@]1(C(=C3CC(C[C@H]3[C@@H]2O)(C)C)C=O)C=O

Technology Process of Merulidial

There total 9 articles about Merulidial 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%

(1aR,5aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3,4,5,5a,6,6a-hexahydro-1H-cyclopropa[f]indene-1a,2-dicarbaldehyde (143836-96-8) → Merulidial (68053-32-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; 0 deg C to r.t.;

DOI:10.1016/S0040-4039(00)61307-2

Reference yield:

(1aR,2S,2aR,6S,6aS)-6,6a-Bis-hydroxymethyl-1a,4,4-trimethyl-1,1a,2,2a,3,4,6,6a-octahydro-cyclopropa[f]inden-2-ol (143836-94-6) → Merulidial (68053-32-7)

Guidance literature:

Multi-step reaction with 3 steps

2: 1.) DMSO, (COCl)2, 2.) (C₂H₅)3N / 1.) CH₂Cl₂, -60 to -50 deg C

3: 81 percent / aq. HF / acetonitrile / 0 deg C to r.t.

With oxalyl dichloride; hydrogen fluoride; dimethyl sulfoxide; triethylamine; In acetonitrile;

DOI:10.1016/S0040-4039(00)61307-2

Reference yield:

C15H18O3 (143836-90-2) → Merulidial (68053-32-7)

Guidance literature:

Multi-step reaction with 7 steps

1: MCPBA, KF / CH₂Cl₂ / 0 °C

2: (i-C₃H₇)2NC₂H₅ / -78 °C

3: LiBF₄ / CHCl₃ / 50 °C / ultrasonication

4: LAH / 1,2-dimethoxy-ethane / 82 °C

6: 1.) DMSO, (COCl)2, 2.) (C₂H₅)3N / 1.) CH₂Cl₂, -60 to -50 deg C

7: 81 percent / aq. HF / acetonitrile / 0 deg C to r.t.

With potassium fluoride; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; hydrogen fluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In 1,2-dimethoxyethane; dichloromethane; chloroform; acetonitrile;

DOI:10.1016/S0040-4039(00)61307-2

upstream raw materials:

(1aR,5aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4,4,6a-trimethyl-3,4,5,5a,6,6a-hexahydro-1H-cyclopropa[f]indene-1a,2-dicarbaldehyde

(1aR,2S,2aR,6S,6aS)-6,6a-Bis-hydroxymethyl-1a,4,4-trimethyl-1,1a,2,2a,3,4,6,6a-octahydro-cyclopropa[f]inden-2-ol

C₁₅H₁₈O₃

C₁₅H₁₆O₄

Downstream raw materials:

Isomerulidial

O-acetylmerulidial

(3α,5α,6β)-6-hydroxy-5,9,9-trimethyl-2-oxotricyclo<5.3.0.0^3,5>-dec-1(7)-ene-3-carbaldehyde

9α-hydroxymerulidial

Refernces