(2S)-N-benzyl-2-({[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carbamothioyl}amino)-N,3,3-trimethylbutanamide

• ChemBase ID: 141431
• Molecular Formular: C36H54N4O2S
• Molecular Mass: 606.90456
• Monoisotopic Mass: 606.39674799
• SMILES: CC(C)(C)c1cc(c(c(c1)C(C)(C)C)O)/C=N\[C@@H]1CCCC[C@H]1NC(=S)N[C@H](C(=O)N(C)Cc1ccccc1)C(C)(C)C
• Canonical SMILES: S=C(N[C@@H](C(C)(C)C)C(=O)N(Cc1ccccc1)C)N[C@@H]1CCCC[C@H]1/N=C\c1cc(cc(c1O)C(C)(C)C)C(C)(C)C
• InChI: InChI=1S/C36H54N4O2S/c1-34(2,3)26-20-25(30(41)27(21-26)35(4,5)6)22-37-28-18-14-15-19-29(28)38-33(43)39-31(36(7,8)9)32(42)40(10)23-24-16-12-11-13-17-24/h11-13,16-17,20-22,28-29,31,41H,14-15,18-19,23H2,1-10H3,(H2,38,39,43)/t28-,29-,31-/m1/s1
• InChIKey: IJFFARBIZKKZOA-QPWMFTQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-benzyl-2-({[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carbamothioyl}amino)-N,3,3-trimethylbutanamide
• IUPAC Traditional name: (2S)-N-benzyl-2-({[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carbamothioyl}amino)-N,3,3-trimethylbutanamide
• Synonyms: (2S)-2-[[[[(1R,2R)-2-[[[3,5-Bis(tert-butyl)-2-hydroxyphenyl]methylene]amino]cyclohexyl]amino]thioxomethyl]amino]-N-benzyl-N,3,3-trimethylbutanamide; (2S)-2-[[[[(1R,2R)-2-[[[3,5-Bis(1,1-dimethylethyl)-2-hydroxyphenyl]methylene]amino]cyclohexyl]amino]thioxomethyl]amino]-N,3,3-trimethyl-N-(phenylmethyl)butanamide; (S)-2-[[(1R,2R)-2-[[[3,5-Bis(tert-butyl)-2-hydroxyphenyl]methylene]amino]cyclohexyl]thioureido]-N-benzyl-N,3,3-trimethylbutanamide; (2S)-2-[[[[(1R,2R)-2-[[[3,5-双(1,1-二甲基乙基)-2-羟苯基]亚甲基]氨基]环己基]氨基]硫代甲基]氨基]-N,3,3-三甲基-N-(苯基甲基)丁酰胺; (2S)-2-[[[[(1R,2R)-2-[[[3,5-双(叔丁基)-2-羟苯基]亚甲基]氨基]环己基]氨基]硫代甲基]氨基]-N-苄基-N,3,3-三甲基丁酰胺; (S)-2-[[(1R,2R)-2-[[[3,5-双(叔丁基)-2-羟苯基]亚甲基]氨基]环己基]硫脲基]-N-苄基-N,3,3-三甲基丁酰胺

Database IDs

• CAS Number: 479423-24-0
• MDL Number: MFCD10567036
• PubChem SID: 162235665
• PubChem CID: 11157752

CALCULATED PROPERTIES

• Acid pKa: 9.753709
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 7.9114923
• LogD (pH = 7.4): 8.579139
• Log P: 8.602091
• Molar Refractivity: 184.1502 cm^3
• Polarizability: 71.51051 Å^3
• Polar Surface Area: 76.96 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 153-163 °C
• Optical Rotation: [α]22/D -99°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Grade: technical grade
• Empirical Formula (Hill Notation): C36H54N4O2S

DETAILS

Sigma Aldrich - 693472

Application
Catalyst for the Mannich reaction5
Catalyst involved in:
• Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams1
• Aza-Baylid-Hillman reactions2
• Hydrophosphonylation of imines3
• Studies of the effect of structure of molecule on asymmetric Strecker and Mannich reactions4
Packaging
100, 500 mg in glass bottle
Protocols & Applications
Asymmetric Strecker Reactions using Jacobsen Thioureas