(4S,5S)-2-chloro-3,4-dimethyl-5-phenyl-2-(prop-2-en-1-yl)-1,3,2-oxazasilolidine

• ChemBase ID: 141577
• Molecular Formular: C13H18ClNOSi
• Molecular Mass: 267.82662
• Monoisotopic Mass: 267.08461841
• SMILES: C[C@H]1[C@@H](O[Si](N1C)(CC=C)Cl)c1ccccc1
• Canonical SMILES: C=CC[Si]1(Cl)O[C@H]([C@@H](N1C)C)c1ccccc1
• InChI: InChI=1S/C13H18ClNOSi/c1-4-10-17(14)15(3)11(2)13(16-17)12-8-6-5-7-9-12/h4-9,11,13H,1,10H2,2-3H3/t11-,13+,17?/m0/s1
• InChIKey: XHCRAANIMMYPDV-APBZJUGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-2-chloro-3,4-dimethyl-5-phenyl-2-(prop-2-en-1-yl)-1,3,2-oxazasilolidine
• IUPAC Traditional name: (4S,5S)-2-chloro-3,4-dimethyl-5-phenyl-2-(prop-2-en-1-yl)-1,3,2-oxazasilolidine
• Synonyms: (1S,2S)-pseudoephedrine allylchlorosilane; (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazasilolidine; (4S,5S)-2-Chloro-3,4-dimethyl-5-phenyl-2-(2-propenyl)-1-oxa-3-aza-2-silacyclopentane; (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1-oxa-3-aza-2-silacyclopentane; (1S,2S)-伪麻黄碱烯丙基氯硅烷; (4S,5S)-2-氯-3,4-二甲基-5-苯基-2-(2-丙烯基)-1-氧杂-3-氮杂-2-硅杂环戊烷; (4S,5S)-2-烯丙基-2-氯-3,4-二甲基-5-苯基-1,3,2-氧氮杂硅杂环戊烷; (4S,5S)-2-烯丙基-2-氯-3,4-二甲基-5-苯基-1-氧杂-3-氮杂-2-硅杂环戊烷

Database IDs

• CAS Number: 447440-43-9
• MDL Number: MFCD09953823
• PubChem SID: 162235811
• PubChem CID: 10333223

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.19603504
• LogD (pH = 7.4): 0.51350266
• Log P: 3.4638
• Molar Refractivity: 68.421 cm^3
• Polarizability: 29.21389 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 120 °C/5 mmHg
• Flash Point: 100.4 °F; 38 °C
• Density: 1.095 g/mL at 25 °C
• Refractive Index: n20/D 1.517
• Optical Rotation: [α]20/D 72.5°, c = 0.6 in ethanol (200 proof)

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 10-15-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H261-H315-H319-H335
• GHS Precautionary statements: P231 + P232-P261-P305 + P351 + P338-P422
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Empirical Formula (Hill Notation): C13H18ClNOSi

DETAILS

Sigma Aldrich - 706671

Application
Reagent used in the enantioselective allylation of aldehydes3
Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents
• Practical, enantioselective allylation of acylhydrazones1
• Enantioselective allylation of ketimines: synthesis of tertiary carbinamines2
General description
This product is a mixture of diastereomers.
Packaging
1 g in glass bottle
Legal Information
U.S. Patent No. 7,534,905