Cularine

Base Information

• Chemical Name: Cularine
• CAS No.: 479-39-0
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• UNII: GHR9KA38RT
• DSSTox Substance ID: DTXSID80963962
• Nikkaji Number: J79.627A
• Wikidata: Q27106275
• Mol file: 479-39-0.mol

Synonyms:(12aS)-6,9,10-Trimethoxy-1-methyl-2,3,12,12a-tetrahydro-1H-(1)benzoxepino(2,3,4-ij)isoquinoline;cularine

Chemical Property of Cularine

Chemical Property:

• Vapor Pressure: 5.07E-09mmHg at 25°C
• Boiling Point: 470.4°Cat760mmHg
• Flash Point: 136.9°C
• PSA: 40.16000
• Density: 1.178g/cm³
• LogP: 3.52770
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

CULARINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=C3C1CC4=CC(=C(C=C4OC3=C(C=C2)OC)OC)OC
• Isomeric SMILES: CN1CCC2=C3[C@@H]1CC4=CC(=C(C=C4OC3=C(C=C2)OC)OC)OC

Technology Process of Cularine

There total 62 articles about Cularine 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: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+)-Enneaphylline (104420-84-0) → (+)-cularine (479-39-0)

Guidance literature:

In diethyl ether;

DOI:10.1021/jo030287t

Reference yield: 81.0%

methanol (67-56-1) + (+)-cularimine (479-42-5) → (+)-cularine (479-39-0)

Guidance literature:

methanol; (+)-cularimine; With formaldehyd; at 20 ℃; for 4h;

With sodium tetrahydroborate; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.orglett.0c04000

Reference yield:

5-(8-Benzyloxy-7-methoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-2-methoxy-phenylamine (158837-96-8) → (+)-cularine (479-39-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaNO₂; H₂SO₄

1.2: 83 percent / NaN₃ / 0.5 h / 0 °C

2.1: 41.31 mg / TFMSA / CCl₄ / 10 h / -5 °C

3.1: sodium nitrite; sulfuric acid / H₂O / 1 h / 0 °C

3.2: water / 2 h / 60 °C

4.1: 25.47 mg / diethyl ether

5.1: methanol / 10 h

6.1: 34.52 mg / sodium borohydride / methanol / 0 - 20 °C

With sodium tetrahydroborate; trifluorormethanesulfonic acid; sulfuric acid; sodium nitrite; In methanol; tetrachloromethane; diethyl ether; water;

DOI:10.1021/jo030287t

upstream raw materials:

formaldehyd

(+)-cularimine

(1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate

(+/-)-didehydronorcularine

Downstream raw materials:

(+)-Celtisine

(+)-Enneaphylline

(+)-Celtine

(+)-Cularidine

Refernces

• 1、 Huang, Zheng,Ji, Xiang,Lumb, Jean-Philip. "Total Synthesis of (S)-Cularine via Nucleophilic Substitution on a Catechol". supporting information. p. 236 - 241. Retrieved 2021/01/09.
• 2、 De Sousa, Joana D. F.,Rodrigues, José A. R.,Abramovitch, Rudolph A.. "Synthesis of cularine and sarcocapnine via enium ions and a new, highly diastereoselective reductive methylation". . p. 9745 - 9746. Retrieved 2007/10/02.