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Merck

684341

Sigma-Aldrich

(S)-5-(吡咯烷-2-基)-1H-四唑

96%

别名:

(S)-(–)-2-四唑-5-基吡咯烷, 脯氨酸四唑催化剂

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About This Item

经验公式(希尔记法):
C5H9N5
CAS号:
分子量:
139.16
MDL號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22

化驗

96%

形狀

solid

光學活性

[α]20/D -9.0°, c = 1 in methanol

mp

253-258 °C

SMILES 字串

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 密鑰

XUHYQIQIENDJER-BYPYZUCNSA-N

應用

(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

象形圖

Skull and crossbones

訊號詞

Danger

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

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


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分析证书(COA)

Lot/Batch Number

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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)

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