(3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-octahydro-1H-1,3,2-benzodiazasilole

• ChemBase ID: 142415
• Molecular Formular: C23H27Br2ClN2Si
• Molecular Mass: 554.82038
• Monoisotopic Mass: 551.99987709
• SMILES: C=CC[Si]1(N([C@H]2CCCC[C@@H]2N1Cc1ccc(cc1)Br)Cc1ccc(cc1)Br)Cl
• Canonical SMILES: C=CC[Si]1(Cl)N(Cc2ccc(cc2)Br)[C@@H]2[C@@H](N1Cc1ccc(cc1)Br)CCCC2
• InChI: InChI=1S/C23H27Br2ClN2Si/c1-2-15-29(26)27(16-18-7-11-20(24)12-8-18)22-5-3-4-6-23(22)28(29)17-19-9-13-21(25)14-10-19/h2,7-14,22-23H,1,3-6,15-17H2/t22-,23-/m0/s1
• InChIKey: JTYONYYNZDUUGN-GOTSBHOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-octahydro-1H-1,3,2-benzodiazasilole
• IUPAC Traditional name: (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-hexahydro-1,3,2-benzodiazasilole
• Synonyms: (S,S)-1,3-Bis-[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole; (S,S)-2-Allyl-1,3-bis-(4-bromobenzyl)-2-chlorooctahydro-2-1H-1,3,2-benzodiazasilole; (S,S)-1,3-双[(4-溴苯基)甲基]-2-氯八氢-2-(2-丙烯基)-1H-1,3,2-苯并二氮杂硅杂环戊二烯; (S,S)-2-烯丙基-1,3-双(4-溴苯甲基)-2-氯八氢-2-1H-1,3,2-苯并二氮杂硅杂环戊二烯

Database IDs

• MDL Number: MFCD12546043
• PubChem SID: 162236645
• PubChem CID: 11467036

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.606098
• LogD (pH = 7.4): 6.4950156
• Log P: 7.1962
• Molar Refractivity: 127.1201 cm^3
• Polarizability: 51.738922 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 94-99 °C
• Optical Rotation: [α]22/D +54°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C23H27Br2ClN2Si

DETAILS

Sigma Aldrich - 705098

Application
An operationally simple regioselective and enantioselective allylation of beta-diketones to provide tertiary carbinols1
Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents
Packaging
1, 5 g in glass bottle
Legal Information
U.S. Patent No. 7,534,905