(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate

• ChemBase ID: 165311
• Molecular Formular: C23H19ClF3NO3
• Molecular Mass: 449.8500696
• Monoisotopic Mass: 449.10055581
• SMILES: C(=C\[C@@H]1[C@@H](C1(C)C)C(=O)O[C@H](c1cc(ccc1)Oc1ccccc1)C#N)(\Cl)/C(F)(F)F
• Canonical SMILES: N#C[C@@H](c1cccc(c1)Oc1ccccc1)OC(=O)[C@H]1[C@H](C1(C)C)/C=C(/C(F)(F)F)\Cl
• InChI: InChI=1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18+,20-/m1/s1
• InChIKey: ZXQYGBMAQZUVMI-RDDWSQKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
• IUPAC Traditional name: C23H19ClF3NO3
• Synonyms: (1S,3S)-rel-3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propen-1-yl]-2,2-dimethyl-cyclopropanecarboxylic Acid (R)-Cyano(3-phenoxyphenyl)methyl Ester; Karate; Warrior; λ-Cyhalothrin

Database IDs

• CAS Number: 91465-08-6
• PubChem SID: 162259444
• PubChem CID: 6440557

CALCULATED PROPERTIES

• Acid pKa: 10.619197
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.677481
• LogD (pH = 7.4): 5.6772227
• Log P: 5.6774845
• Molar Refractivity: 110.0142 cm^3
• Polarizability: 41.654907 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C988980

Insecticide; pyrethrin analog

REFERENCES

• Bhavani, B., et al.: Pestol., 33, 42 (2009)
• Patial, A., et al.: Env. Ecol., 27, 320 (2009)
• Schleier, J., et al.: J. Med. Entomol., 46, 693 (2009)
• Yang, D., et al.: Toxicol. App. Pharmacol., 237, 49 (2009)