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427055

Sigma-Aldrich

1-Boc-四氢吡咯

97%

别名:

1-吡咯烷甲酸叔丁酯

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About This Item

经验公式（希尔记法）:
C9H17NO2
CAS号:
86953-79-9
分子量:
171.24
MDL號碼:
MFCD00216581
分類程式碼代碼:
12352100
PubChem物質ID:
24866734
NACRES:
NA.22

品質等級

100

化驗

97%

形狀

liquid

折射率

n20/D 1.449 (lit.)

bp

80 °C/0.2 mmHg (lit.)

密度

0.977 g/mL at 25 °C (lit.)

SMILES 字串

CC(C)(C)OC(=O)N1CCCC1

InChI

1S/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3

InChI 密鑰

LPQZERIRKRYGGM-UHFFFAOYSA-N

相关类别

一般說明

N-Boc-pyrrolidine is an N-substituted pyrrolidine. It is reported that the reactivity of N-Boc-pyrrolidine towards C-H insertion reaction is 2000 times more than cyclohexane. It undergoes α-arylation in the presence of a palladium catalyst with high enantioselectivity.

應用

N-Boc-pyrrolidine may be used in the synthesis of the following:
  • 2-aryl-N-boc-pyrrolidines
  • scalemic 2-pyrrolidinylcuprates
  • 2-alkenyl-N-Boc-pyrrolidines
  • 1-deoxycastanospermine
  • methylphenidate analogues
  • (+)-elaeokanine A

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險聲明

H315,H319,H335

危險分類

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

10 - Combustible liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

186.8 °F - closed cup

閃點（°C）

86 °C - closed cup

個人防護裝備

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
SHBB0643V
67796DJ
00220LH
00122KE
15628CA

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Enantioselective, palladium-catalyzed α-arylation of N-boc-pyrrolidine.
Campos KR, et al.
Journal of the American Chemical Society, 128(11), 3538-3539 (2006)
Copper mediated scalemic organolithium reagents in alkaloid syntheses.
3Dieter RK, et al.
Tetrahedron, 61(13), 3221-3230 (2005)
Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites.
Davies HML, et al.
Bioorganic & Medicinal Chemistry Letters, 14(7), 1799-1802 (2004)
Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine.
Majewski M, et al.
Tetrahedron Letters, 39(38), 6787-6790 (1998)
Graeme Barker et al.
The Journal of organic chemistry, 76(15), 5936-5953 (2011-07-01)
A comprehensive study of the enantioselective Pd-catalyzed α-arylation of N-Boc pyrrolidine has been carried out. The protocol involves deprotonation of N-Boc pyrrolidine using s-BuLi/(-)-sparteine in TBME or Et(2)O at -78 °C, transmetalation with ZnCl(2) and Negishi coupling using Pd(OAc)(2), t-Bu(3)P-HBF(4)
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