(-)-Fenchone - 10mM in DMSO , CAS No.7787-20-4

CAS: 7787-20-4 Cat. No.: F425924 Molecular Weight: 152.24 EC Number: 232-107-5

GRADE & PURITY 10mM in DMSO

Synonyms

UNII-K6G5Y2Y3Q2 | (-)-Fenchone, analytical standard | 2H-Indol-2-one, 7-benzoyl-1,3-dihydro- | Bicyclo(2.2.1)heptan-2-one, 1,3,3-trimethyl-, (1theta)- | Fenchon | METHYL 5-CHLORO-2-NITROBENZENECARBOXYLATE | Ferri (59 Fe) citratis injectio | Bicyclo[2.2.1]

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

(-)-Fenchone is a bridged bicyclic ketone found in fennel oil and thuja oil.
(-)-Fenchone undergoes condensation with pyridinylalkylamines to form chiral iminopyridine ligands, which find applications in enantioselective copper-catalyzed Henry (nitro aldol) reaction.It may also be used in the preparation of enantiopure C(7)-anti-substituted fenchones as new chiral sources.

Specifications

Synonyms

UNII-K6G5Y2Y3Q2 | (-)-Fenchone, analytical standard | 2H-Indol-2-one, 7-benzoyl-1, 3-dihydro- | Bicyclo(2.2.1)heptan-2-one, 1, 3, 3-trimethyl-, (1theta)- | Fenchon | METHYL 5-CHLORO-2-NITROBENZENECARBOXYLATE | Ferri (59 Fe) citratis injectio | Bicyclo[2.2.1]

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC1(C2CCC(C2)(C1=O)C)C
• IUPAC Name: (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
• InChIKey: LHXDLQBQYFFVNW-OIBJUYFYSA-N
• INCHI: 1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
• Isomeric SMILES: C[C@@]12CC[C@@H](C1)C(C2=O)(C)C
• WGK Germany: 3
• UN Number: 3082
• Packing Group: III
• Molecular Weight: 152.24
• Reaxy-Rn: 1861492
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1861492&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Bicyclic monoterpenoids
• Alternative Parents: Ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Fenchane monoterpenoid - Bicyclic monoterpenoid - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
• External Descriptors: Bicyclic monoterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Refractive Index: 1.4600 to 1.4630
• Specific Rotation[α]: -50.0 to -55.0 deg(neat)
• Flash Point(°F): 125.6 °F
• Flash Point(°C): 52°C
• Boil Point(°C): 193°C
• Melt Point(°C): 5-6°C
• Molecular Weight: 152.230 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.12 Da
• Monoisotopic Mass: 152.12 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 217.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yixiang Li, Yajun Bai, Tai-Ping Fan, Xiaohui Zheng, Yujie Cai.  (2021)  Characterization of a putative tropinone reductase from Tarenaya hassleriana with a broad substrate specificity.  BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY,  69  (6): (2530-2539).  [PMID:34902878] [10.1002/bab.2302]