99615-99-3

Basic information

• Product Name: clarkeanidine
• Synonyms: clarkeanidine
• CAS NO: 99615-99-3
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.37434
• Mol File: 99615-99-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 447.8°Cat760mmHg
• Flash Point: 224.6°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.23E-08mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: clarkeanidine(CAS DataBase Reference)
• NIST Chemistry Reference: clarkeanidine(99615-99-3)
• EPA Substance Registry System: clarkeanidine(99615-99-3)

Safety Data

• Hazardous Substances Data: 99615-99-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H21NO4/c1-23-15-6-4-12-9-14-17-11(3-5-16(24-2)19(17)22)7-8-20(14)10-13(12)18(15)21/h3-6,14,21-22H,7-10H2,1-2H3/t14-/m0/s1

Upstream product

• 50-00-0 formaldehyd 

Relevant articles and documents

Total Synthesis of the Ortho-Hydroxylated Protoberberines (S)-Govaniadine, (S)-Caseamine, and (S)-Clarkeanidine via a Solvent-Directed Pictet-Spengler Reaction

The common para regioselectivity in Pictet-Spengler reactions with dopamine derivatives is redirected to the ortho position by a simple change of solvents. In combination with a chiral auxiliary on nitrogen, this ortho-selective Pictet-Spengler produced the 1-benzyltetrahydroisoquinoline alkaloids (S)-crassifoline and (S)-norcrassifoline and the bioactive 1,2-dioxygenated tetrahydroprotoberberine alkaloids (S)-govaniadine, (S)-caseamine, and (S)-clarkeanidine with high enantiopurity. Ortho/para ratios up to 89:19 and diastereomeric ratios up to 85:15 were obtained during formation of the B-ring. The general applicability of this solvent-directed regioselectivity was demonstrated with a second Pictet-Spengler reaction as required for C-ring formation of caseamine (o/p = 14:86 in trifluoroethanol) and clarkeanidine (o/p = 86:14 in toluene).