(3R)-3-hydroxy-4,4-dimethyloxolan-2-one

• ChemBase编号: 110070
• 分子式: C6H10O3
• 平均质量: 130.1418
• 单一同位素质量: 130.06299418
• SMILES: CC1(C)COC(=O)[C@@H]1O
• Canonical SMILES: O[C@H]1C(=O)OCC1(C)C
• InChI: InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChIKey: SERHXTVXHNVDKA-BYPYZUCNSA-N

名称和登记号

名称

• IUPAC标准名: (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• IUPAC传统名: pantolactone
• 别名: (R)-(-)-α-羟基-β,β-二甲基-γ-丁内酯; (R)-(-)-β,β-二甲基-α-羟基-γ-丁内酯; (R)-(-)-泛内酯; 泛解酸γ-内酯; D-(-)-泛酰内酯; D-(-)-Pantolactone; D-α-HYDROXY-β,β-DIMETHYL-γ-BUTYROLACTONE; (R)-(-)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (R)-(-)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone; (R)-(-)-Pantolactone; Pantoic acid γ-lactone; (R)-(-)-4,5-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; D-(-)-alpha-Hydroxy-beta,beta-dimethyl-gamma-butyrolactone; (3R)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; (-)-(R)-Pantolactone; (-)-2-Hydroxy-3,3-dimethyl-γ-butyrolactone; (-)-Pantoyl Lactone; (3R)-Tetrahydro-3-hydroxy-4,4-dimethylfuran-2-one; Pantothenic Lactone; D-(-)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (R)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; D-(-)-Pantolactone

登记号

• CAS号: 599-04-2
• EC号: 209-963-3
• MDL号: MFCD00005392
• Beilstein号: 80957
• 默克索引号: 147013
• PubChem SID: 162096418; 24854272; 24879245
• PubChem CID: 439368

理论计算性质

• Acid pKa: 12.228233
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.17736644
• LogD (pH = 7.4): 0.17736007
• Log P: 0.17736652
• 摩尔折射率: 30.516 cm^3
• 极化性: 12.506425 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 89-91°C; 89-92 °C; 91 °C(lit.)
• 沸点: 120-122 °C/15 mmHg(lit.); 120-122°C/15mm
• 比旋光度: [α]20/D -51±2°, c = 3% in H2O; [α]25/D -49.8°, c = 2 in H2O; -51 (c=3 in water)

安全信息

• 保存注意事项: Hygroscopic
• 德国WGK号: 1
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99.0% (T); 99%
• 级别: puriss.
• Empirical Formula (Hill Notation): C6H10O3

详细说明

MP Biomedicals - 05213625

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P2625

Other Notes
Degradation product of pantothenic acid.

Sigma Aldrich - 237817

包装
5, 25 g in glass bottle

Sigma Aldrich - 55200

Other Notes
用作手性结构单元：还原成三醇1；酰胺化2；简便地获得环氧乙烷的两种对映体：S(+)- 和 R(-)-2,2-二甲基-3,4-环氧丁醇3

Toronto Research Chemicals - P182500

An important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia.

参考文献

• Williams, M.: Science, 91, 246 (1940)
• Glaser et al.: Monatsch. Chem., 25, 46 (1940)
• Stiller et al.: J. Am. Chem. Soc., 62, 1785 (1940)
• Dorofeev, B.F. et al.: Dep. Doc., 14 (1940)
• Chiral auxiliary for enantioselective Diels-Alder reactions. Esters with acrylic acids react with dienes to give adducts with exo-endo selectivity and high ee: Tetrahedron Lett., 26, 3095 (1985); 30, 5599 (1989); Tetrahedron: Asymmetry, 1, 537 (1990). Preferred chiral auxiliary for kinetic resolution of ɑ-amino esters: Tetrahedron Lett., 34, 4473 (1993); J. Org. Chem., 64, 7700 (1999).