510-67-8

Basic information

• Product Name: (-)-Crinine【C16 alkaloid】
• Synonyms: (-)-Crinine【C16 alkaloid】;(3R)-1,2-Didehydrocrinan-3-ol;1,2-Didehydrocrinan-3α-ol;Crinidine;Crinine;Crinine【C16 alkaloid】
• CAS NO: 510-67-8
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.31
• Mol File: 510-67-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 456.3°C at 760 mmHg
• Flash Point: 229.8°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 4.04E-09mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: (-)-Crinine【C16 alkaloid】(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Crinine【C16 alkaloid】(510-67-8)
• EPA Substance Registry System: (-)-Crinine【C16 alkaloid】(510-67-8)

Safety Data

• Hazardous Substances Data: 510-67-8(Hazardous Substances Data)

Usage

General Description

(-)-Crinine is a C16 alkaloid that is found in various plant species such as Narcissus and Lycoris. It possesses a range of pharmacological properties, including anti-tumor and anti-inflammatory effects. It has been shown to inhibit the growth of various cancer cells, such as breast cancer and prostate cancer cells, and has potential as a therapeutic agent for cancer treatment. In addition, (-)-Crinine also exhibits anti-inflammatory properties by inhibiting the production of inflammatory mediators such as nitric oxide and cytokines. Overall, (-)-Crinine shows promise as a natural compound with potential medicinal uses, particularly in the treatment of cancer and inflammation.

InChI:InChI=1/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2

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Relevant articles and documents

Asymmetric synthesis method for crinum asiaticum alkaloid

The invention relates to an asymmetric synthesis method for crinum asiaticum alkaloid taking the asymmetric catalytic hydrogenation reaction as the key step. According to the method, through racemic asymmetric catalytic hydrogenation kinetic resolution for replacing cyclohexanone, quick asymmetric synthesis for 22 kinds of crinum asiaticum alkaloid comprising (-)-crinine, (+)-epivittatine, (+)-vittatine, (-)-epicrinine and the like and eight analogues is achieved concisely and efficiently.

Asymmetric total synthesis of gracilamine and determination of its absolute configuration

(+)-Gracilamine, a biologically attractive and structurally unique pentacyclic Amaryllidaceae alkaloid, was biomimetically synthesized in 11 linear steps in 9.9% overall yield from the known racemic oxocrinine. The synthesis features an asymmetric hydrogenation, a ring-opening/benzylic oxidation/cyclization sequence, and a biomimetic intramolecular cycloaddition. This total synthesis not only allows the assignment of its absolute configuration, but also provides experimental support for the hypothesis that naturally occurring (+)-gracilamine is biogenetically derived from the crinine-type alkaloid (+)-epivittatine.

Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization

Polycyclic alkaloids bearing all-carbon quaternary centers possess a diversity of biological activities and are challenging targets in natural product synthesis. The development of a general and asymmetric catalytic method applicable to the efficient syntheses of a series of complex polycyclic alkaloids remains highly desirable in synthetic chemistry. Herein we describe an efficient palladium-catalyzed enantioselective dearomative cyclization which is capable of synthesizing two important classes of tricyclic nitrogen-containing skeleton, chiral dihydrophenanthridinone and dihydrocarbazolone derivatives bearing all-carbon quaternary centers, in excellent yields and enantioselectivities. The P-chiral monophosphorus ligand AntPhos is crucial for the reactivity and enantioselectivity, and the choice of the N-phosphoramide protecting group is essential for the desired chemoselectivity. This method has enabled the enantioselective total syntheses of three distinctive and challenging biologically important polycyclic alkaloids, specifically a concise and gram-scale synthesis of (-)-crinine, an efficient synthesis of indole alkaloid (-)-aspidospermidine and a formal enantioselective synthesis of (-)-minfiensine.