Licarin B

Base Information

• Chemical Name: Licarin B
• CAS No.: 51020-87-2
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• DSSTox Substance ID: DTXSID601317642
• Nikkaji Number: J585.124F,J238.371C
• Wikidata: Q104396883
• Metabolomics Workbench ID: 129883
• ChEMBL ID: CHEMBL259386
• Mol file: 51020-87-2.mol

Synonyms:licarin B

Chemical Property of Licarin B

Chemical Property:

• Vapor Pressure: 3.78E-07mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 428.5 °C at 760 mmHg
• Flash Point: 131.4 °C
• PSA: 36.92000
• Density: 1.201 g/cm³
• LogP: 4.69420
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 324.13615911
• Heavy Atom Count: 24
• Complexity: 465

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-LicarinB >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CC1=CC2=C(C(=C1)OC)OC(C2C)C3=CC4=C(C=C3)OCO4
• Isomeric SMILES: C/C=C/C1=CC2=C(C(=C1)OC)O[C@H]([C@@H]2C)C3=CC4=C(C=C3)OCO4

Technology Process of Licarin B

There total 12 articles about Licarin B 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%

threo-2-<2'-hydroxy-3'-methoxy-5'-(1-propenyl)>phenyl-1-piperonylpropanol (140423-82-1,140423-83-2) → (+/-)-licarin B (23342-98-5,42016-15-9,51020-87-2,55515-49-6)

Guidance literature:

With acetic acid; for 1h; Heating;

DOI:10.1248/cpb.39.3123

Reference yield:

(E)-propenyl-tri-n-butylstannane (105494-65-3,66680-85-1,66680-84-0) + 5-((2S,3S)-5-Iodo-7-methoxy-3-methyl-2,3-dihydro-benzofuran-2-yl)-benzo[1,3]dioxole → (+/-)-licarin B (23342-98-5,42016-15-9,51020-87-2,55515-49-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; lithium chloride; In N,N-dimethyl-formamide; at 120 - 130 ℃; Yield given;

DOI:10.1016/0040-4039(96)01619-X

Reference yield:

N-(3-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide (168648-79-1) → (+/-)-licarin B (23342-98-5,42016-15-9,51020-87-2,55515-49-6)

Guidance literature:

Multi-step reaction with 7 steps

1: BF₃*Et₂O / CH₂Cl₂ / -78 °C

2: KOtBu / tetrahydrofuran / 60 - 70 °C

3: Na, anthracene / tetrahydrofuran / 23 °C

4: F₃CCO₂H / CH₂Cl₂ / 23 °C

5: 1.) NaNO₂, 50percent aq. HOAc, 2.) K₂CO₃ / 1.) 0 deg C, 2.) water, 0 deg C

6: Me₃SiCl, NaI / acetonitrile

7: Pd₂(dba)3, (2-furyl)3P, LiCl / dimethylformamide / 120 - 130 °C

With chloro-trimethyl-silane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; anthracene; boron trifluoride diethyl etherate; potassium tert-butylate; sodium; potassium carbonate; acetic acid; trifluoroacetic acid; sodium iodide; lithium chloride; sodium nitrite; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)01619-X

upstream raw materials:

threo-2-<2'-hydroxy-3'-methoxy-5'-(1-propenyl)>phenyl-1-piperonylpropanol

(E)-propenyl-tri-n-butylstannane

N-(3-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide

isosafrole

Refernces

• 1、 Watanabe,Kawanishi,Akiyoshi,Furukawa. "A regioselective lithiation of ortho-cresols using the bis(dimethylamino)phosphoryl group as a directing group: General synthesis of 2,3-dihydrobenzo[b]furans including naturally occurring neolignans". . p. 3123 - 3131. Retrieved 2007/10/02.