(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl 4-phenylbenzoate

• ChemBase编号: 126709
• 分子式: C21H20O5
• 平均质量: 352.3805
• 单一同位素质量: 352.13107374
• SMILES: OC[C@H]1[C@@H](C[C@@H]2OC(=O)C[C@H]12)OC(=O)c1ccc(cc1)c1ccccc1
• Canonical SMILES: OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC(=O)c1ccc(cc1)c1ccccc1
• InChI: InChI=1S/C21H20O5/c22-12-17-16-10-20(23)25-18(16)11-19(17)26-21(24)15-8-6-14(7-9-15)13-4-2-1-3-5-13/h1-9,16-19,22H,10-12H2/t16-,17-,18+,19-/m1/s1
• InChIKey: SZJVIFMPKWMGSX-AKHDSKFASA-N

名称和登记号

名称

• IUPAC标准名: (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl 4-phenylbenzoate
• IUPAC传统名: corey lactone 4-phenylbenzoate
• 别名: (3aα,4α,5β,6aα)-(-)-六氢-4-(羟甲基)-2-氧代-2H-环戊并[b]呋喃-5-基1,1′-联苯-4-甲酸酯; (3aR,4S,5R,6aS)-六氢-4-羟甲基-5-(4-苯基苯甲酰氧基)环戊并[b]呋喃-2-酮; (-)-科里内酯4-苯基苯甲酸醇; (3aα,4α,5β,6aα)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1′-biphenyl-4-carboxylate; (3aR,4S,5R,6aS)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one; (-)-Corey lactone, 4-phenylbenzoate alcohol; Corey lactone 4-phenylbenzoate; (3aR,4S,5R,6aS)-Hexahydro-4-(hydroxymethyl)-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one; (-)-Corey Lactone 4-Phenylbenzoate Alcohol; Corey Lactone; (-)-Corey Lactone 5-(4-Phenylbenzoate)

登记号

• CAS号: 31752-99-5
• MDL号: MFCD00078077
• Beilstein号: 1294692
• PubChem SID: 162221037; 24854983
• PubChem CID: 2724295
• 维基百科标题: Corey_lactone_4-phenylbenzoate

理论计算性质

• Acid pKa: 15.374329
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.6427593
• LogD (pH = 7.4): 2.6427593
• Log P: 2.6427593
• 摩尔折射率: 94.8059 cm^3
• 极化性: 38.50716 Å^3
• 极化表面积: 72.83 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Off-White to Pale Yellow Solid
• 熔点: 131-132 °C; 131-132 °C(lit.); 133-135°C
• 比旋光度: [α]20/D -87°, c = 1 in chloroform; [α]20/D -88±1°, c = 1% in chloroform

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 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% (sum of enantiomers, HPLC); 99%
• 级别: purum
• Empirical Formula (Hill Notation): C21H20O5

详细说明

Sigma Aldrich - 249262

包装
1 g in glass bottle
Application
合成前列腺素的关键中间体。1,2前列腺素的通用结构单元。用于制备强效和选择性抗青光眼药物 PGF2α的类似物的结构单元2

Sigma Aldrich - 52535

Other Notes
合成前列腺素的重要中间体1,2

Toronto Research Chemicals - C695000

Key intermediate in the synthesis of prostaglandins. Versatile building block for prostaglandins. Building block for a potent and selective antiglaucoma agent analog of PGF2α.

参考文献

• Carpio, H., et al.: Prostaglandins, 33, 169 (1987)
• Resul, B., et al.: J. Med. Chem., 36, 243 (1987)