(4S)-4-benzyl-1,3-oxazolidin-2-one

• ChemBase编号: 149354
• 分子式: C10H11NO2
• 平均质量: 177.19984
• 单一同位素质量: 177.0789786
• SMILES: c1ccc(cc1)C[C@H]1COC(=O)N1
• Canonical SMILES: O=C1OC[C@@H](N1)Cc1ccccc1
• InChI: InChI=1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1
• InChIKey: OJOFMLDBXPDXLQ-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: (4S)-4-benzyl-1,3-oxazolidin-2-one
• IUPAC传统名: (4S)-4-benzyl-1,3-oxazolidin-2-one
• 别名: (S)-4-苄基-2-噁唑烷酮; (S)-(-)-4-苄基氧氮杂环戊烷酮; (S)-4-Benzyl-2-oxazolidinone; (S)-(-)-4-Benzyl-2-oxazolidinone; (S)-4-Benzyloxazolidin-2-one; (4S)-4-benzyl-1,3-oxazolidin-2-one; (4S)-4-(Phenylmethyl)-2-oxazolidinone; (-)-4-Benzyl-2-oxazolidinone; (4S)-4-(Phenylmethyl)-1,3-oxazolidin-2-one; (4S)-4-Benzyl-1,3-oxazolidin-2-one; (4S)-Benzyloxazolidin-2-one; (S)-4-Benzyl-2-oxazolidinone

登记号

• CAS号: 90719-32-7
• MDL号: MFCD00064496
• Beilstein号: 3649667
• PubChem SID: 24857725; 162243521; 24848262
• PubChem CID: 736225

理论计算性质

• Acid pKa: 13.030782
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 1.7140553
• LogD (pH = 7.4): 1.7140545
• Log P: 1.7140553
• 摩尔折射率: 48.055 cm^3
• 极化性: 18.866823 Å^3
• 极化表面积: 38.33 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: White Crystalline Solid
• 熔点: 86 - 88°C; 86-88 °C; 86-88 °C(lit.); 86-88°C; 87-89°C
• 比旋光度: [α]20/D -63°, c = 1 in chloroform; [α]20/D -64±2°, c = 1% in chloroform; -64 (c=1 in chloroform)
• 疏水性(logP): 1.325

安全信息

• 保存注意事项: Hygroscopic
• 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); 95%; 97%; 98%; 99%
• 级别: puriss.
• 光学纯度: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C10H11NO2

详细说明

Sigma Aldrich - 294640

Application
手性助剂，最近用于合成 (S)-雌马酚。用于制备和官能化稳定的手性叶立德。
用于不对称合成 (3R)- 和 (3S)-六氢哒嗪-3-羧酸。1
用于不对称烷化反应的手性助剂。
包装
25 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - B285825

An oxazolidinone used in chiral auxiliary asymetric synthesis.

参考文献

• Evans chiral auxiliary; compare (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.
• For details of use in enantioselective aldol condensation, see: Org. Synth. Coll., 8, 339 (1993):
  
• A simplified method of acylation of the oxazolidinone, avoiding the need for rigorously anhydrous conditions, has been reported using acyl chlorides, anhydrides or pivaloyl mixed anhydrides as the acylating agents catalyzed by DMAP: Synthesis, 1283 (1996).
• See also (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.