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Merck
CN

684341

Sigma-Aldrich

(S)-5-(吡咯烷-2-基)-1H-四唑

96%

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别名:
(S)-(–)-2-四唑-5-基吡咯烷, 脯氨酸四唑催化剂
经验公式(希尔记法):
C5H9N5
CAS号:
分子量:
139.16
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

96%

形式

solid

旋光性

[α]20/D -9.0°, c = 1 in methanol

mp

253-258 °C

SMILES字符串

C1CN[C@@H](C1)c2nnn[nH]2

InChI

1S/C5H9N5/c1-2-4(6-3-1)5-7-9-10-8-5/h4,6H,1-3H2,(H,7,8,9,10)/t4-/m0/s1

InChI key

XUHYQIQIENDJER-BYPYZUCNSA-N

应用

(S)-(−)-5-(2-Pyrrolidinyl)-1H-tetrazole can be used as an organocatalyst:
  • To prepare enantioselective chiral 1,2-oxazines from achiral ketones via an intramolecular Wittig reaction.
  • To synthesize diastereoselective Michael addition products by addition of aliphatic aldehydes to β-nitrostyrene.
  • In the direct asymmetric α-fluorination of linear and branched aldehydes using N-fluorobenzenesulfonamide as the fluorinating agent.

Organocatalyst used for:
  • Direct asymmetric aldol reactions between acetone and aldehydes yielding β -hydroxy ketone and for synthesizing 1,1,1-trichloro-2-alkanols
  • Mannich reactions for synthesis fo α -amino acids and generation of 1,4-diamines
  • Conjugate additions of malonates to enones

象形图

Skull and crossbones

警示用语:

Danger

危险分类

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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访问文档库

Oelke, A. et al.
Synlett, 2548-2548 (2006)
Sirirat Kumarn et al.
Chemical communications (Cambridge, England), (30), 3211-3213 (2006-10-10)
A sequential, organocatalysed asymmetric reaction to access chiral 1,2-oxazines from achiral ketone starting materials is reported, which proceeds in moderate to good yields and excellent enantioselectivity.
Direct asymmetric α-fluorination of aldehydes
Steiner DD, et al.
Angewandte Chemie (International Edition in English), 117(24), 3772-3776 (2005)
A highly selective, organocatalytic route to chiral 1, 2-oxazines from ketones
Kumarn S, et al.
Chemical Communications (Cambridge, England), 3211-3213 (2006)
Asymmetric organocatalyzed Michael addition of aldehydes to β-nitrostyrene in ionic liquids
Mevciarova M, et al.
Tetrahedron Asymmetry, 20(20), 2403-2406 (2009)

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