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Merck
CN

457701

(S)-(-)-2-甲基-CBS-噁唑硼烷 溶液

1 M in toluene

别名:

α,α-二苯基-L-脯氨醇甲基硼酸环胺酯, (S)-1-甲基-3,3-二苯基-四氢-吡咯并[1,2c][1,3,2]噁唑硼烷, (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

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关于此项目

经验公式（希尔记法）:
C18H20BNO
化学文摘社编号:
112022-81-8
分子量:
277.17
NACRES:
NA.22
PubChem Substance ID:
24869386
UNSPSC Code:
12352005
MDL number:
MFCD00078439

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产品名称

(S)-(-)-2-甲基-CBS-噁唑硼烷 溶液, 1 M in toluene

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

SMILES string

CB1OC([C@@H]2CCCN12)(c3ccccc3)c4ccccc4

InChI key

VMKAFJQFKBASMU-KRWDZBQOSA-N

concentration

1 M in toluene

bp

111 °C

density

0.929 g/mL at 25 °C

functional group

phenyl

storage temp.

room temp

Quality Level

100

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相关类别

Application

用于不对称还原和不对称合成的CBS催化剂
CBS (Corey-Bakshi-Shibata) 噁唑硼烷催化剂已被用于前手性酮的非对称性还原。其他应用包括 α-羟基酸、α-氨基酸、C2 对称二茂铁二醇以及炔丙醇的对映选择性合成。
用于 (S)-2-氨基-1-苯乙醇的对映选择性合成的催化剂。
用于非对称性还原反应的优良催化剂。
(S)-(-)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the multi-step synthesis of (-)-diospongin A.
It may also be used in the preparation of:
  • (1S)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
  • (R)-α-deuteriobenzyl alcohol
  • (R)-2-(1-hydroxyethyl)benzo[b]thiophene

Other Notes

储存时可能形成沉淀，但不影响产品质量。在惰性气体环境下将产品缓慢加热至 80-90°C，使固体再溶解。

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

target_organs

Central nervous system

存储类别

3 - Flammable liquids

wgk

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
SHBR4393
0000008124
SHBH5749
0000007545
SHBH6193

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Organic Process Research & Development, 10, 893-893 (2006)
Diastereoselective photochromism of a bisbenzothienylethene governed by steric as well as electronic interactions.
Yokoyama Y, et al.
Journal of the American Chemical Society, 125(24), 7194-7195 (2003)
Enantioselective synthesis of (S)-salmeterol via asymmetric reduction of azidoketone by Pichia angusta.
Procopiou PA, et al.
Tetrahedron Asymmetry, 12(14), 2005-2008 (2001)
Stereoselective synthesis of (-)-diospongins A and B and their stereoisomers at C-5.
Kawai N, et al.
Tetrahedron, 63(37), 9049-9056 (2007)
Bis (oxazoline)-ligand-mediated asymmetric [2, 3]-Wittig rearrangement of benzyl ethers: reaction mechanism based on the hydrogen/deuterium exchange effect.
Kitamura M, et al.
Tetrahedron, 68(22), 4280-4285 (2012)
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商品

CBS Catalysts

we are pleased to offer both enatiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1M solution in toluene.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

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