(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase编号: 77362
• 分子式: C10H11NO2
• 平均质量: 177.19984
• 单一同位素质量: 177.0789786
• SMILES: N1Cc2c(cccc2)C[C@@H]1C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1NCc2c(C1)cccc2
• InChI: InChI=1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m1/s1
• InChIKey: BWKMGYQJPOAASG-SECBINFHSA-N

名称和登记号

名称

• IUPAC标准名: (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC传统名: (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• 别名: (R)-1,2,3,4-四氢-3-异喹啉羧酸; (R)-(+)-1,2,3,4-四氢异喹啉-3-羧酸; (R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid; (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid; H-D-Tic-OH; (R)-(+)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; (-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid; L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid; L-3-Carboxy-1,2,3,4-tetrahydroisoquinoline; L-Porretine; (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid

登记号

• CAS号: 74163-81-8; 103733-65-9
• MDL号: MFCD00144038
• Beilstein号: 5378782
• PubChem SID: 162042235; 24888899
• PubChem CID: 712398

理论计算性质

• Acid pKa: 1.8478861
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -1.2092154
• LogD (pH = 7.4): -1.213396
• Log P: -1.2092786
• 摩尔折射率: 48.4455 cm^3
• 极化性: 18.996552 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Basic Water; Hot Water
• 外观: Off-White Solid
• 熔点: >225°C (dec.)
• 比旋光度: [α]20/D +164±3°, c = 2% in 1 M NaOH; +163 (c=2 in 1N NaOH)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Irritant
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98.0% (T); 95+%
• 杂质: ≤1% water
• Empirical Formula (Hill Notation): C10H11NO2
• 分类: Derivatives & analogs of Natural Compounds

详细说明

Sigma Aldrich - 87433

Other Notes
D-苯丙氨酸具有空间位阻的类似物1；对映选择性还原助剂2

Toronto Research Chemicals - T293755

Quinapril intermediate.

参考文献

• Cheng, S., et al.: Eur. J. Med. Chem., 44, 4904 (2009)
• Brust, A., et al.: J. Med. Chem., 52, 6991 (2009)
• Toussaint, M., et al.: Eur. Neuropsychopharmacol., 19, 504 (2009)