(2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-6',8'-diene-5,5'-dione

• ChemBase编号: 170318
• 分子式: C22H28O4
• 平均质量: 356.45532
• 单一同位素质量: 356.19875938
• SMILES: C1C(=O)C=C2[C@](C1)(C1C(C=C2)C2[C@](C[C@H]1O)([C@]1(CC2)OC(=O)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C=CC1C2[C@H](O)C[C@]2(C1CC[C@]12CCC(=O)O1)C)C
• InChI: InChI=1S/C22H28O4/c1-20-8-5-14(23)11-13(20)3-4-15-16-6-9-22(10-7-18(25)26-22)21(16,2)12-17(24)19(15)20/h3-4,11,15-17,19,24H,5-10,12H2,1-2H3/t15?,16?,17-,19?,20+,21+,22-/m1/s1
• InChIKey: RJTDWMKVQUPGSY-GOAYFHFKSA-N

名称和登记号

名称

• IUPAC标准名: (2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-6',8'-diene-5,5'-dione
• IUPAC传统名: (2R,2'R,15'S,17'R)-17'-hydroxy-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-6',8'-diene-5,5'-dione
• 别名: (11α,17α)-11,17-Dihydroxy-3-oxopregna-4,6-diene-21-carboxylic Acid γ-Lactone; 11α-Hydroxy Canrenone

登记号

• CAS号: 192569-17-8
• PubChem SID: 164226228
• PubChem CID: 45358387

理论计算性质

• Acid pKa: 14.880123
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.286634
• LogD (pH = 7.4): 2.286634
• Log P: 2.286634
• 摩尔折射率: 99.0753 cm^3
• 极化性: 38.58536 Å^3
• 极化表面积: 63.6 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

• 溶解度: Acetone; Chloroform; Methanol
• 外观: Yellow Solid
• 熔点: 232-234°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - H883500

11α-Hydroxy Canrenone is the key intermediate in the synthesis of Eplerenone, a cardiovascular drug. Canrenone was biotransformed into 11α-Hydroxycanrenone by Aspergillus ochraceus SIT34205.

参考文献

• Luetscher, J., et al.: J. Clin. Invest., 29, 1576 (1950)
• Gaunt, R., et al.: J. Clin. Endocrinol. Metab., 15, 621 (1950)
• McMahon, E., et al.: Curr. Opin. Pharm., 1, 190 (1950)
• McMahon, E., et al.: Curr. Pharm. Des., 9, 1065 (1950)