(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

• ChemBase编号: 92245
• 分子式: C6H11NO2
• 平均质量: 129.15704
• 单一同位素质量: 129.0789786
• SMILES: N1[C@H](COC1=O)C(C)C
• Canonical SMILES: CC([C@H]1COC(=O)N1)C
• InChI: InChI=1S/C6H11NO2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1
• InChIKey: YBUPWRYTXGAWJX-RXMQYKEDSA-N

名称和登记号

名称

• IUPAC标准名: (4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one
• IUPAC传统名: (4S)-4-isopropyl-1,3-oxazolidin-2-one
• 别名: (S)-(-)-4-异丙基-2-噁唑烷酮; (4S)-(-)-异丙基-2-恶唑啉酮; (S)-(-)-4-Isopropyl-2-oxazolidinone; (S)-4-Isopropyl-2-oxazolidinone; 4(S)-(1-Methylethyl)-2-oxazolidinone; 4(S)-Isopropyloxazolidin-2-one; (S)-(-)-4-Isopropyl-2-oxazolidinone; (4s)-(-)-4-isopropyl-2-oxazolidinone; (4S)-(-)-Isopropyl-2-oxazolidinone; (4R)-4-Isopropyl-1,3-oxazolidin-2-one

登记号

• CAS号: 95530-58-8; 17016-83-0
• MDL号: MFCD00075172; MFCD00010847
• Beilstein号: 3588198
• PubChem SID: 24881639; 24858002; 162078943
• PubChem CID: 7157133

理论计算性质

• Acid pKa: 13.160297
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 0.94522417
• LogD (pH = 7.4): 0.9452235
• Log P: 0.94522417
• 摩尔折射率: 32.4316 cm^3
• 极化性: 12.991205 Å^3
• 极化表面积: 38.33 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; Ethanol
• 外观: White to off-White Solid
• 熔点: 70-72°C; 70-73 °C; 70-73 °C(lit.); 70-73°C; 70-74°C
• 比旋光度: [α]20/D +14±1°, c = 7% in chloroform; [α]20/D -18°, c = 6 in ethanol; -17 (c=6 in ethanol)

安全信息

• 保存注意事项: Irritant
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99.0% (sum of enantiomers, GC); 98%; 99%
• 级别: purum
• 光学纯度: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C6H11NO2

详细说明

Sigma Aldrich - 298883

Application
用作二铑络合物中的手性配体1，以及羟醛加成反应中的手性辅助剂。2用于不对称合成的多功能手性助剂。最新综述，请参阅 Alrichimica Acta。3
包装
1, 5 g in glass bottle

Sigma Aldrich - 59660

Other Notes
该 3-酰基衍生物可用于很多对映选择性反应：3-丙酰基衍生物用于羟醛反应1,2,3；以及烷基化反应4

参考文献

• Alkyl carboxamides derived from the N-acylation of the oxazolidinone form enolates which undergo highly enantioselective aldol condensation with aldehydes. The products readily undergo hydrolysis, e.g. with base, to give chiral ? -hydroxyacids, with consequent easy recovery and recycle of the chiral auxiliary: J. Am. Chem. Soc., 103, 2127 (1981); Tetrahedron, 27, 897 (1986); Tetrahedron Lett., 31, 4699 (1990); J. Org. Chem., 56, 2489 (1991). For reaction scheme, see (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.
• The enolates of the N-acyloxazolidinones can also undergo a variety of other enantioselective reactions including alkylation: J. Am. Chem. Soc., 104, 1737 (1982); acylation: J. Am. Chem. Soc., 106, 1154 (1984):
  
• Bromination (NBS), followed by azide displacement, gives a route to chiral amino acids: Tetrahedron Lett ., 28, 1123 (1987). Direct electrophilic azidation with triisopropylbenzenesulfonyl azide has also been used to effect this transformation: J. Am. Chem. Soc., 112, 4011 (1990).
• Chiral auxiliary introduced by Evans for use in enantioselective reactions.
• See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.