(-)-Sparteine (-)-鹰爪豆碱

CAS 90-39-1 MFCD00069653

化学结构图

90-39-1
SMILES: C1CCN2CC3CC(CN4CCCCC34)C2C1

化学属性

Mol. FormulaC15H26N2
Mol. Weight234.38
Refractive index1.5260 to 1.5300
Boiling Point
Density1.02
Flash Point-
TSCANo
Melting PointNo Data Available

别名和识别编码

Chemical Name(-)-Sparteine
MDL Number-
CAS Number90-39-1
Synonym (-)-Sparteine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID644020
EC Number201-988-8
Merck Number8737
Beilstein Registry Number23(2)97
Chemical Name Translation(-)-鹰爪豆碱
InChIKeyWNSDDGBLIALDPB-UUABGMMQSA-N
Reaxys-RN82447
Wiswesser Line NotationT C66 K66 A HN PNTJ
LabNetwork Molecule IDLN01377943
InChIInChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1
Canonical SMILES-
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分类

  • {SA} Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Deprotonation

产品应用

  • 用于手性二苯基甲烷的锂化/烷化中的非对称控制，以及在制备手性磷化氢配体中异构选择性地脱质子化。
  • 和Cu(II)结合成有机催化剂，用于异构体选择性合成硝基醇醛。

相关文献及参考

  • Chiral base used by Beak, Hoppe and others as chiral ligand in asymmetric lithiation reactions with alkyllithium reagents. High ee values are often obtained and the ligand can be easily recycled. For details of asymmetric lithiation of 1-Boc-pyrrolidine, see: J. Am. Chem. Soc., 116, 3231 (1994); Org. Synth. Coll., 9, 391 (1998); for comparison with other ligands, see: J. Org. Chem., 60, 8148 (1995). For reviews of asymmetric lithiation reactions of this type, see: Acc. Chem. Res., 29, 552 (1996), and of enantioselective synthesis with Li/sparteine carbanion pairs: Angew. Chem. Int. Ed., 36, 2283 (1997).

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H332 Harmful if inhaled 吸入有害
  • H302 Harmful if swallowed 吞食有害
  • H312 Harmful in contact with skin 皮肤接触有害
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSWG5950000
Precautionary statements
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P332+P313
  • P305+P351+P338+P337+P313
  • P301+P312+P330
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P302+P350
  • P337+P313
Signal word Warning
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
Storage condition 0-10°C 2-8°C, protect from light, stored under nitrogen 4 4°C, Inert atmosphere Air Sensitive 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 960 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans
   Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium)  V.4-   
   1898-  Volume(issue)/page/year: 210,27,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 220 mg/kg
TOXIC EFFECTS :
   Behavioral - tremor
   Behavioral - muscle contraction or spasticity
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   PLMEAA Planta Medica.  (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart
   1, Fed. Rep. Ger.) V.1-    1953-  Volume(issue)/page/year: 50,420,1984

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 30 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig,
   Ger. Dem. Rep.)  Volume(issue)/page/year: 4,1398,1935

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Amphibian - frog
DOSE/DURATION           : 1665 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig,
   Ger. Dem. Rep.)  Volume(issue)/page/year: 4,1398,1935

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Ro

系列性分类

  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Deprotonation - Chiral Catalysts, Ligands, and Reagents
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Alkaloids

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