(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

112022-81-8
SMILES: CB1OC(c2ccccc2)(c2ccccc2)C2CCCN12

化学属性

Mol. FormulaC18H20BNO
Mol. Weight277.17
Density0.929
Boiling Point111
Flash Point4°(39°F)
TSCANo
Melting Point87-91
Refractive indexn20/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 NumberMFCD00078439
PubChem Substance ID2734713
Beilstein Registry Number8492123
CAS Number112022-81-8
EC Number250-023-7
Reaxys-RN8492123
Chemical Name Translation(S)-2-甲基-CBS-恶唑硼烷
InChIInChI=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 IDLN00162856
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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

Precautionary statements
Hazard statements
  • 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
WGK Germany3
Signal word
GHS Symbol
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter dust mask type N95 (US), Eyeshields, Gloves
Safety Statements
  • 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；
Packing GroupII
UN Number
Risk Statements
  • 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
Storage condition 0-10 Air & Moisture Sensitive 0-10°C Refrigerator
Hazard Codes
Hazard Class3

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

系列性分类

  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  1. Chemical Synthesis 化学合成
  2. Catalysis and Inorganic Chemistry 催化剂和无机化学
  3. Boron 硼
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Reduction - Chiral Catalysts, Ligands, and Reagents
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Boronic Acids and Derivatives 硼酸和硼酸衍生物
  4. Boranes
  1. Functional Group 官能团索引
  2. boronic acid ester
  1. Corey Catalyst 科里催化剂
  2. Boron 硼
  1. Organocatalyst
  2. Boron
  1. Catalysts
  2. Boron

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