844657-46-1

Basic information

• Product Name: (8α,9R)- 9-(9-phenanthrenyloxy)-Cinchonan-6'-ol
• Synonyms: (8α,9R)- 9-(9-phenanthrenyloxy)-Cinchonan-6'-ol;4-((1R)-(Phenanthren-9-yloxy)((2S)-5-vinylquinuclidin-2-yl)Methyl)quinolin-6-ol;(8α,9R)-9-(9-Phenanthrenyloxy)cinchonan-6'-ol,99%d.e.
• CAS NO: 844657-46-1
• Molecular Formula: C33H30N2O2
• Molecular Weight: 486.6
• Mol File: 844657-46-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (8α,9R)- 9-(9-phenanthrenyloxy)-Cinchonan-6'-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (8α,9R)- 9-(9-phenanthrenyloxy)-Cinchonan-6'-ol(844657-46-1)
• EPA Substance Registry System: (8α,9R)- 9-(9-phenanthrenyloxy)-Cinchonan-6'-ol(844657-46-1)

Safety Data

• Hazardous Substances Data: 844657-46-1(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
(8α,9R)9-(9-phenanthrenyloxy)-Cinchonan-6'-ol is used as a chiral catalyst or ligand in asymmetric synthesis for its ability to induce enantioselectivity in chemical reactions. This application is crucial for the production of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals, agrochemicals, and fragrances.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (8α,9R)9-(9-phenanthrenyloxy)-Cinchonan-6'-ol is used as a key intermediate or building block in the synthesis of biologically active molecules. Its unique structure and reactivity can be exploited to develop new drugs with improved potency, selectivity, and pharmacokinetic properties.
Used in Drug Discovery and Development:
(8α,9R)9-(9-phenanthrenyloxy)-Cinchonan-6'-ol's potential as a pharmacophore makes it valuable in drug discovery and development. Researchers can use (8α,9R)9-(9-phenanthrenyloxy)-Cinchonan-6'-ol as a starting point to design and optimize new drug candidates targeting various therapeutic areas, such as infectious diseases, central nervous system disorders, and cancer.
Used in Organic Synthesis:
(8α,9R)9-(9-phenanthrenyloxy)-Cinchonan-6'-ol can also be employed in organic synthesis as a versatile building block for the preparation of a wide range of organic compounds. Its unique structural features and reactivity make it suitable for the synthesis of complex organic molecules, which can find applications in various fields, such as materials science, supramolecular chemistry, and nanotechnology.

Upstream product

• 130-95-0 Quinine 
• 17024-12-3 9-iodo-phenanthrene 
• 56-54-2 quinindine 
• 174654-07-0 quinidine 9-O-(9'-phenanthryl)ether 

Relevant articles and documents

ASYMMETRIC MICHAEL AND ALDOL ADDITION USING BIFUNCTIONAL CINCHONA-ALKALOID-BASED CATALYSTS

One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with 5 base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral 10 ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.

Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids

The development of readily accessible bifunctional chiral catalysts is a desirable yet challenging goal in catalytic asymmetric synthesis. In this communication, we describe the development of a new class of readily accessible chiral bifunctional organic catalysts that could be derived in one or two steps in high yield from either quinidine or quinine. These catalysts have been shown to catalyze a highly enantioselective conjugate addition of methyl and ethyl malonates and β-ketoesters to a broad range of β-substituted nitroalkenes, an synthetically important C-C bond-forming reaction utilizing readily available starting materials. This new catalytic asymmetric reaction proceeds in 91-98% ee and 71-99% yield. Copyright