427055
1-Boc-四氢吡咯
97%
别名:
1-吡咯烷甲酸叔丁酯
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关于此项目
经验公式（希尔记法）:
C9H17NO2
CAS Number:
分子量:
171.24
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
质量水平
方案
97%
表单
liquid
折射率
n20/D 1.449 (lit.)
沸点
80 °C/0.2 mmHg (lit.)
密度
0.977 g/mL at 25 °C (lit.)
SMILES字符串
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 key
LPQZERIRKRYGGM-UHFFFAOYSA-N
一般描述
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.
应用
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
警示用语：
Warning
危险声明
危险分类
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官
Respiratory system
储存分类代码
10 - Combustible liquids
WGK
WGK 3
闪点(°F)
186.8 °F - closed cup
闪点(°C)
86 °C - closed cup
个人防护装备
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Copper mediated scalemic organolithium reagents in alkaloid syntheses.
3Dieter RK, et al.
Tetrahedron, 61(13), 3221-3230 (2005)
Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine.
Majewski M, et al.
Tetrahedron Letters, 39(38), 6787-6790 (1998)
Enantioselective, palladium-catalyzed α-arylation of N-boc-pyrrolidine.
Campos KR, et al.
Journal of the American Chemical Society, 128(11), 3538-3539 (2006)
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)
R Karl Dieter et al.
The Journal of organic chemistry, 71(15), 5674-5678 (2006-07-15)
The key transformation in the total synthesis of (+)-elaeokanine A was accomplished by asymmetric deprotonation of N-Boc pyrrolidine, followed by the reaction of the in situ generated enantioenriched stereogenic cuprate reagent with (E)-4-bromo-1-iodo-1-trimethylsilyl-1-butene with retention of configuration. N-Boc deprotection, followed
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