(S)-3,3-Diphenyl-1-Methyltetrahydro-1H,3H-Pyrrolo[1,2-c][1,3,2]Oxazaborole (S)-2-甲基-CBS-恶唑硼烷
CAS 112022-81-8 MFCD00078439
化学结构图
SMILES: CB1OC(c2ccccc2)(c2ccccc2)C2CCCN12
化学属性
| Mol. Formula | C18H20BNO |
|---|---|
| Mol. Weight | 277.17 |
| Density | 0.929 |
| Boiling Point | 111 |
| Flash Point | 4°(39°F) |
| TSCA | No |
| Melting Point | 87-91 |
| Refractive index | n20/D 1.460 |
| Stability | 空气和水分敏感 |
| Appearance | liq. |
别名和识别编码
| Chemical Name | (S)-3,3-Diphenyl-1-Methyltetrahydro-1H,3H-Pyrrolo[1,2-c][1,3,2]Oxazaborole |
|---|---|
| Synonym | ALPHA,ALPHA-DIPHENYL-L-PROLINOL METHYLBORONIC ACID CYCL-AMIDE ESTER (S)-2-METHYL-CBS-OXAZABOROLIDINE, 1M IN& (S)-ME CBS (S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE (S)--2-甲基-CBS-氧杂硼啶 (s)-methyloxazaborolidine,(s)-mecbs,intoluene (s)-methyloxazaborolidine,(s)-mecbs,in (S)-Methyl oxazaborolidine, in toluene, 1M solution (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (S)-Methyloxazaborolidine,1-1.5Mintoluene[(S)-MeCBS] (S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE (S)-甲基恶唑硼烷 (S)-1-METHYL-3,3-DIPHENYL-TETRAHYDRO-PYRROLO[1,2C][1,3,2]OXAZABOROLE (S)-2-METHYL-CBS-OXAZABOROLIDINE, 1M SOL UTION IN TOLUENE (S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-P YRROLO-OXAZABOROLE (S)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (s)-methyl (S)-2-甲基-CBS-恶唑硼烷 (S)-2-甲基-CBS-氧杂硼啶单水合物 (S)-(-)-2-METHYL-CBS-OXAZABOROLIDINE (S)--2-甲基-CBS-氧杂硼啶, 1M 甲苯溶液 (S)-(-)-2-甲基-CBS-噁唑硼烷 溶液 (S)-(+)-甲基-CBS-恶唑硼烷 (S)-METHYL OXAZABOROLIDINE (S)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE (S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE (S)-(-)-2-甲基-CBS-噁唑硼烷 (S)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H PYRROLO[1,2-C][1,3,2] OXAZABOROLE (S)-2-METHYL-CBS-OXAZABOROLIDINE α,α-二苯基-L-脯氨醇甲基硼酸环胺酯 (S)-3,3-二苯基-1-甲基四氢-3H-吡咯并[1,2-c][1,3,2]噁唑硼烷 (S)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷 (S)-1-甲基-3,3-二苯基-四氢-吡咯并[1,2c][1,3,2]噁唑硼烷 |
| MDL Number | MFCD00078439 |
| PubChem Substance ID | 2734713 |
| Beilstein Registry Number | 8492123 |
| CAS Number | 112022-81-8 |
| EC Number | 250-023-7 |
| Reaxys-RN | 8492123 |
| Chemical Name Translation | (S)-2-甲基-CBS-恶唑硼烷 |
| InChI | InChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m0/s1 |
| LabNetwork Molecule ID | LN00162856 |
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分类
- {SNA} Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
相关文献及参考
- For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992).
- Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217): J. Am . Chem. Soc., 109, 7925 (1987):
- For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of ɑ-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).
- Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (S)-2-Methyl-CBS-oxazaborolidine, L14583.
- For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).
- Anhydrous catalyst for 'CBS' reduction reaction. For examples of use in asymmetric reduction of ketones, see: Org. Synth. Coll., 9, 362, 676 (1998). For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
安全信息
- H315 Causes skin irritation 会刺激皮肤
- H319 Causes serious eye irritation 严重刺激眼睛
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
- H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
- H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
- H361d Suspected of damaging the unborn child 怀疑对未出生婴儿造成伤害
- H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
- H351 Suspected of causing cancer 怀疑致癌
GHS Symbol
- S46 If swallowed, seek medical advice immediately and show this container or label 食入时，立即求医并出示容器/标签；
- S62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label where possible 吞食后不要催吐：立即求医并出示该容器或标签；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
- S33 Take precautionary measures against static discharges 对静电采取预防措施；
- S29 Do not empty into drains 不要排入下水道；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- R11 Highly flammable 非常易燃
- R19 May form explosive peroxides 可能生成易爆的过氧化物质
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
其他信息
- TCI Shanghai:(S)-2-甲基-CBS-恶唑硼烷 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine,>;98.0%(T)(112022-81-8)
- 稳定性:(S)-2-甲基-CBS-恶唑硼烷（112022-81-8）极易和空气中的水发生水解使其催化活性降低。
- 敏感性:Air & Moisture Sensitive
- 用途一:Yield very high enantiseletivity in reduction of ketones. The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones.Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids,3 C2 symmetrical ferrocenyl diols, and propargyl alcohols.
- 外观:无色或浅黄色液体（甲苯溶液）
- 存储注意事项:热敏感
- (S)-2-甲基-CBS-恶唑硼烷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 D2131 (S)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 5G 2330元 2011/04/16 D2131 (S)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 1G 688元 2010/06/21 369770050 (S)-2-甲基-CBS-恶唑硼烷 (S)-2-Methyl-CBS-oxazaborolidine , 1M solution in toluene 5 ML 836元
- F:10-21
- (S)-2-甲基-CBS-恶唑硼烷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D2131 (S)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 5G 2370元 2014/06/02 D2131 (S)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 1G 682元 2010/06/21 369770050 (S)-2-甲基-CBS-恶唑硼烷 (S)-2-Methyl-CBS-oxazaborolidine , 1M solution in toluene 5 ML 836元
- Alfa Aesar:(S)-2-甲基-CBS-氧杂硼啶单水合物,94% (S)-2-Methyl-CBS-oxazaborolidine monohydrate, 94%(112022-81-8)
- MOL 文件:112022-81-8.mol
- 上游原料:四氢呋喃 --> 二氯甲烷 --> 氧氯化硫 --> L-脯氨酸 --> 溴化苯基镁 --> 三甲基环三硼氧烷
