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Merck

678538

Sigma-Aldrich

(-)-Ipc2B(烯丙基)硼烷

1 M in pentane

别名:

(-)-B-二异松莰烯基烯丙基硼

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25 ML
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About This Item

线性分子式:
(C10H17)2BCH2CH=CH2
CAS号:
分子量:
326.37
MDL编号:
UNSPSC代码:
12352002
PubChem化学物质编号:
NACRES:
NA.22

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旋光性

[α]20/D −35 to ±5°, c = 1

质量水平

浓度

1 M in pentane

沸点

35-36 °C

密度

0.638 g/mL at 25 °C

储存温度

−20°C

SMILES字符串

C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B(CC=C)[C@@H]3C[C@@H]4C[C@H]([C@H]3C)C4(C)C

InChI

1S/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m1/s1

InChI key

ZIXZBDJFGUIKJS-RLEROFIGSA-N

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应用

方便、无盐且稳定的手性烯丙基硼烷溶液,用于醛的不对称烯丙基化反应,生成手性高烯丙醇。[1][2]

其他说明

本品冷却储藏时可能会变浑浊,不影响使用
Under refrigerator storage, these salt-free, Ipc2B(allyl) reagents do not show any appreciable decrease in selectivity is observed after several months. They exhibit excellent reactivity and reactions can be performed at 5°C, even in water.[3]

警示用语:

Danger

危险分类

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 1 - Skin Irrit. 2 - STOT SE 3

靶器官

Central nervous system, Respiratory system

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

-56.2 °F - closed cup

闪点(°C)

-49 °C - closed cup

个人防护装备

Eyeshields, Faceshields, Gloves


历史批次信息供参考:

分析证书(COA)

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Enantio-and diastereoselective synthesis of ?-substituted-?-aminoboronic esters from nitriles
Ramachandran, P. Veeraraghavan, et al.
Tetrahedron Letters, 54.36, 4830-4833 (2013)
Stereoselective Synthesis of 2, 6?Disubstituted Piperidines Using the Iridium?Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)?241 D and Related Piperidine Alkaloids.
Gnamm, Christian, et al.
European Journal of Chemistry, 15.9, 2050-2054 (2009)
Aldrichimica Acta, 25, 23-23 (2002)
Versatile route to 2, 6-dideoxyamino sugars from non-sugar materials: Syntheses of vicenisamine and kedarosamine.
Matsushima, Yoshitaka, et al.
J. Chem. Soc., Perkin Trans., 1.6, 569-577 (2001)
Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach
Ramesh, Perla, Atla Raju, and Nitin W. Fadnavis.
Tetrahedron Asymmetry, 26.21, 1251-1255 (2015)

相关内容

Asymmetric allylboration of aldehydes is an extremely important method for preparation of homoallylic alcohols, as evidenced in numerous complex natural product syntheses.

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