(7R,12S,18S)-12-methyl-6-methylidene-17-oxa-14-azahexacyclo[10.6.3.15,8.01,11.02,8.014,18]docosan-7-ol

Base Information

• Chemical Name: (7R,12S,18S)-12-methyl-6-methylidene-17-oxa-14-azahexacyclo[10.6.3.15,8.01,11.02,8.014,18]docosan-7-ol
• CAS No.: 76-53-9
• Molecular Formula: C₂₂H₃₃NO₂
• Molecular Weight: 343.51
• NSC Number: 304674
• Mol file: 76-53-9.mol

Synonyms:VEATCHINE;NSC304674;NSC-304674;76-53-9;5H,11-Methano-6,13b-propanocyclohept[h]oxazolo[2,3-a]isoquinolin-9-ol, dodecahydro-6-methyl-10-methylene-

Chemical Property of (7R,12S,18S)-12-methyl-6-methylidene-17-oxa-14-azahexacyclo[10.6.3.15,8.01,11.02,8.014,18]docosan-7-ol

Chemical Property:

• Vapor Pressure: 2.55E-11mmHg at 25°C
• Melting Point: 119-120°
• Boiling Point: 482.2°Cat760mmHg
• Flash Point: 245.4°C
• PSA: 32.70000
• Density: 1.19g/cm³
• LogP: 3.51620
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 343.251129295
• Heavy Atom Count: 25
• Complexity: 634

Purity/Quality:

99% ^*data from raw suppliers

VEATCHINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC3(C1CCC45C3CCC(C4)C(=C)C5O)C6N(C2)CCO6
• Isomeric SMILES: C[C@]12CCCC3(C1CCC45C3CCC(C4)C(=C)[C@H]5O)[C@H]6N(C2)CCO6
• Description: This alkaloid occurs in Garrya species and is a major constituent of G. veatchii. It is laevorotatory with [α]27.5D - 69.01°. The crystalline hydrochloride has m.p. 2Sl-2°C (dec.); hydrobromide, m.p. 229-2300 C and the hydriodide, m.p. 222-3°C (dec.). The O-acetate has m.p. l52-3°C and yields a hydrochloride, m.p. 258-9°C. The structure has been determined by chemical analysis and from spectroscopic data.

Technology Process of (7R,12S,18S)-12-methyl-6-methylidene-17-oxa-14-azahexacyclo[10.6.3.15,8.01,11.02,8.014,18]docosan-7-ol

There total 12 articles about (7R,12S,18S)-12-methyl-6-methylidene-17-oxa-14-azahexacyclo[10.6.3.15,8.01,11.02,8.014,18]docosan-7-ol 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: 96.0%

oxirane (75-21-8,99932-75-9) + lindheimerine (68831-67-4) → garryfoline (76-53-9,509-30-8,11018-10-3,62014-63-5,76984-76-4,21913-33-7,28596-06-7)

Guidance literature:

In methanol; at 25 ℃; for 15h;

DOI:10.1021/jo00322a020

Reference yield:

ovatine (68719-14-2,70614-02-7,76984-75-3) → garryfoline (76-53-9,509-30-8,11018-10-3,62014-63-5,76984-76-4,21913-33-7,28596-06-7)

Guidance literature:

With potassium carbonate; In methanol; Ambient temperature;

DOI:10.1021/jo00322a020

Reference yield:

garryfoline azomethine (76946-28-6) → garryfoline (76-53-9,509-30-8,11018-10-3,62014-63-5,76984-76-4,21913-33-7,28596-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / Ambient temperature; overnight

2: 96 percent / methanol / 15 h / 25 °C

In pyridine; methanol;

DOI:10.1021/jo00322a020

upstream raw materials:

ovatine

oxirane

veatchine azomethine acetate

veatchine acetate

Downstream raw materials:

Garryin

Isocuavchichicin

ovatine

lindheimerine

Refernces

• 1、 Pelletier,Mody,Desai. "Structures of cuauchichicine, garryfoline, lindheimerine, and ovatine. Chemical correlation of cuauchichicine with (-)'β'-dihydrokaurene". . p. 1840 - 1846. Retrieved 2007/10/02.