(3aS,6R,7aS)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one

• ChemBase编号: 90766
• 分子式: C12H18O6
• 平均质量: 258.26772
• 单一同位素质量: 258.1103383
• SMILES: O1C(OC[C@@]21C(=O)[C@@H]1[C@@H](OC(O1)(C)C)CO2)(C)C
• Canonical SMILES: O=C1[C@H]2OC(O[C@H]2CO[C@]21COC(O2)(C)C)(C)C
• InChI: InChI=1S/C12H18O6/c1-10(2)15-6-12(18-10)9(13)8-7(5-14-12)16-11(3,4)17-8/h7-8H,5-6H2,1-4H3/t7-,8-,12+/m0/s1
• InChIKey: IVWWFWFVSWOTLP-YVZVNANGSA-N

名称和登记号

名称

• IUPAC标准名: (3aS,6R,7aS)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
• IUPAC传统名: (3aS,6R,7aS)-2,2,5',5'-tetramethyl-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
• 别名: 史氏环氧化反应催化剂对映体; 1,2:4,5-双-O-(异亚丙基)-β-L-赤式-2,3-二酮-2,6-吡喃糖; Shi epoxidation catalyst; L-enantiomer; 1,2:4,5-Bis-O-(isopropylidene)-beta-L-erythro-2,3-hexodiulo-2,6-pyranose; Shi epoxidation catalyst enantiomer; 1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose

登记号

• CAS号: 198965-05-8
• MDL号: MFCD16621458
• PubChem SID: 162077497
• PubChem CID: 11391247

理论计算性质

• 极化性: 24.3432 Å^3
• 极化表面积: 63.22 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true
• Acid pKa: 15.104746
• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): 1.4142153
• LogD (pH = 7.4): 1.4142153
• Log P: 1.4142153
• 摩尔折射率: 60.0832 cm^3

分子性质

理化性质

• 熔点: 98-104 °C; 98-104°C
• 比旋光度: [α]22/D +111.0°, c = 0.5 in chloroform

安全信息

• 保存注意事项: Harmful
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302

产品相关信息

• Empirical Formula (Hill Notation): C12H18O6

详细说明

Sigma Aldrich - 718653

包装
250 mg in glass bottle
Application
Reactant for:
• Diastereoselective synthesis of a-tocopherol via Shi epoxidation1
• Synthesis of benzimidazole-based analogs of epothilone A with anticancer activity2Catalyst for:
• Preparation of microtubule-stabilizing and antitumor active analogs of epothilone3
• Synthesis of (+)-aurilol via regio- and stereocontrolled A-D ether ring formations4