237701
S-Alpine-Borane® 溶液
0.5 M in THF
别名:
B-异松蒎基-9-硼二环[3.3.1]壬烷
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关于此项目
经验公式（希尔记法）:
C18H31B
化学文摘社编号:
分子量:
258.25
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352000
MDL number:
InChI
1S/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13+,14-,15+,16-,17-/m0/s1
SMILES string
C[C@@H]1[C@H](C[C@H]2C[C@@H]1C2(C)C)B3[C@@H]4CCC[C@H]3CCC4
InChI key
VCDGSBJCRYTLNU-NEXGVSGLSA-N
form
liquid
optical activity
[α]22/D +1.2°, neat
concentration
0.5 M in THF
density
0.897 g/mL at 25 °C
General description
S-Alpine-Borane® is a chiral reducing agent, synthesized from (-)-α-pinene via hydroboration.
Application
R- 和 S-Alpine-Boranes 用于醛和前手性酮的不对称还原反应。
S-Alpine-Borane® solution may be used to prepare:
- 5(S)-methyl 5-hydroxy-8-(tetrahydropyran-2-yloxy)-6-octynoate, an intermediate for the stereocontrolled total synthesis of leukotriene B4.
- (+)-(S)-4-hydroxy-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
- (R)-1-(tert-Butyldiphenylsilyloxy)pent-3-yn-2-ol, an intermediate for the preparation of (S)-4,5-dihydroxypentane-2,3-dione (DPD).
Legal Information
Alpine-Borane is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Pyr. Liq. 1 - STOT SE 3
target_organs
Respiratory system
supp_hazards
存储类别
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 3
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
危险化学品
此项目有
(-)-Sparteine-Mediated Stereoselective Intramolecular Carbolithiation of 4-Substituted 5-Hexynyl Carbamates. Synthesis of Enantiopure 1, 3-Difunctionalized Alkylidene Cyclopentanes.
Oestreich M, et al.
The Journal of Organic Chemistry, 64(23), 8616-8626 (1999)
An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
Ascenso OS, et al.
Bioorganic & Medicinal Chemistry, 19(3), 1236-1241 (2011)
Tetrahedron Asymmetry, 5, 1061-1061 (1994)
Total synthesis of leukotriene B4.
Kerdesky FAJ, et al.
The Journal of Organic Chemistry, 58(13), 3516-3520 (1993)
Synlett, 561-561 (1993)
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