(1R,5R,7R)-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-3,3-dione

• ChemBase编号: 295313
• 分子式: C10H17NO2S
• 平均质量: 215.31248
• 单一同位素质量: 215.09799979
• SMILES: CC1([C@@H]2CC[C@]31CS(=O)(=O)N[C@@H]3C2)C
• Canonical SMILES: O=S1(=O)N[C@H]2[C@@]3(C1)CC[C@H](C2)C3(C)C
• InChI: InChI=1S/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10+/m1/s1
• InChIKey: DPJYJNYYDJOJNO-MRTMQBJTSA-N

名称和登记号

名称

• IUPAC标准名: (1R,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• IUPAC传统名: (1R,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• 别名: (1R,2S)-(+)-2,10-樟脑磺内酰胺; (2S)-(+)-Bornane-10,2-sultam; (1R,2S)-(+)-10,2-Camphorsultam

登记号

• CAS号: 108448-77-7
• MDL号: MFCD00151762
• Beilstein号: 4675755
• PubChem SID: 180680844
• PubChem CID: 23308448

理论计算性质

• Acid pKa: 10.407443
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.5864519
• LogD (pH = 7.4): 0.5860786
• Log P: 0.58645666
• 摩尔折射率: 53.6538 cm^3
• 极化性: 22.299479 Å^3
• 极化表面积: 46.17 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: 179-186°C
• 比旋光度: +33 (c=1 in ethanol)

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A

产品相关信息

• 纯度: 99%

参考文献

• Versatile chiral auxiliary introduced by Oppolzer. Review: Tetrahedron, 49, 293 (1993). The N-acyl derivatives undergo various transformations in a highly enantioselective manner:
• N-Acryloyl derivatives undergo enantioselective cycloaddition reactions: Helv. Chim. Acta, 67, 1397 (1984); Tetrahedron, 43, 1969 (1987). Hydrogenation of N-acryloyl derivatives proceeds with high diastereoselectivity: Tetrahedron Lett., 27, 183 (1986); Helv. Chim. Acta, 69, 1542 (1986), 69, 1817 (1986); 70, 1666 (1987). Induces asymmetric conjugate addition of Grignard reagents to N-acryloyl derivatives: Helv. Chim. Acta, 70, 2201 (1987). In the presence of strong bases, N-acyl derivatives undergo stereoselective alkylation: Tetrahedron Lett., 30, 5603 (1989); or aldol-type condensation reactions with aldehydes: J. Am. Chem. Soc., 112, 2767 (1990); Tetrahedron Lett., 32, 61 (1991).
• Chiral auxiliary for the asymmetric Baylis-Hillman reaction (see 1,4-Diazabicyclo[2.2.2]octane, A14003): J. Am. Chem. Soc., 119, 4317 (1997).