496786-98-2
中文名称
4-[5-(4,4,5,5-四甲基-1,3,2-DIOXABOROLAN-2-基)哌啶-2-基]哌嗪-1-羧酸叔丁酯
英文名称
4-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS
496786-98-2
分子式
C20H32BN3O4
MDL 编号
MFCD04039875
分子量
389.3
MOL 文件
496786-98-2.mol
更新日期
2025/08/15 16:47:49
496786-98-2 结构式
基本信息
中文别名
4-[5-(4,4,5,5-四甲基-1,3,2-DIOXABOROLAN-2-基)哌啶-2-基]哌嗪-1-羧酸叔丁酯6-(4-BOC-1-哌嗪并)吡啶-3-硼酸频哪醇酯
英文别名
2-(4-BOC-PIPERAZIN-1-YL)PYRIDINE-5-BORONIC ACID PINACOL ESTER2-(4-BOC-PIPERAZINE)PYRIDINE-5-BORONIC ACID PINACOL ESTER
2-(4-TERT-BUTOXYCARBONYLPIPERAZIN-1-YL)PYRIDINE-5-BORONIC ACID, PINACOL ESTER
4-(5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-2-YL)-1-BOC-PIPERAZINE
4-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
6-(4-TERT-BUTOXYCARBONYLPIPERAZINYL)PYRIDINE-3-BORONIC ACID, PINACOL ESTER
TERT-BUTYL 4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2-PYRIDINYL]TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE
TERT-BUTYL 4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-2-YL]PIPERAZINE-1-CARBOXYLATE
6-(4-Boc-piperazin-1-yl)pyridine-3-boronic acid pinacol ester, 96%
4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]piperazine-1-carboxylic acid tert-butyl ester
4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl-piperazine-1-carboxylic acid tert-butyl ester
tert-Butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine-1-carboxylate 97%
6-(4-BOC-1-PIPERAZINO)PYRIDINE-3-BORONIC ACID PINACOL ESTER
6-[4-(tert-Butoxycarbonyl)piperazin-1-yl]pyridine-3-boronic acid pinacol ester
4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl-piperazine-1-carboxylic acid t
tert-Butyl 4-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylüpiperazine-1-carboxylate
tert-Butyl 4-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylüpiperazine-1-carboxylate
tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]tetrahydro-1(2H)-pyrazinecarboxylate
2-[4-(N-Boc)piperazin-1-yl]pyridine-5-boronic acid pinacol ester
6-(4-Boc-1-piperazinyl)pyridine-3-boronic acid pinacol ester
所属类别
有机原料：杂环化合物物理化学性质
熔点165-169 °C
沸点515.9±50.0 °C(Predicted)
密度1.14±0.1 g/cm3(Predicted)
储存条件Keep in dark place,Sealed in dry,Room Temperature
酸度系数(pKa)8.41±0.31(Predicted)
形态solid
外观White to off-white Solid
InChIInChI=1S/C20H32BN3O4/c1-18(2,3)26-17(25)24-12-10-23(11-13-24)16-9-8-15(14-22-16)21-27-19(4,5)20(6,7)28-21/h8-9,14H,10-13H2,1-7H3
InChIKeyJWUBVPJWWYYRLJ-UHFFFAOYSA-N
SMILESN1(C(OC(C)(C)C)=O)CCN(C2=NC=C(B3OC(C)(C)C(C)(C)O3)C=C2)CC1
制备方法
方法1
73183-34-3
153747-97-8
496786-98-2
在氮气保护下，将4-Boc-1-(5-溴-2-吡啶基)哌嗪（125g，366mmol）溶于DMF（1.30L）中，依次加入联硼酸频那醇酯（186g，732mmol）、醋酸钯（4.09g，18.3mmol）、三苯基膦（19.2g，73.2mmol）和醋酸钾（108g，1.10mol）。将反应混合物在80℃下搅拌反应过夜。反应完成后，冷却至室温，过滤收集固体。滤液在减压下浓缩，所得残余物通过硅胶快速柱色谱法（洗脱剂：乙酸乙酯/石油醚，1:50 v/v）纯化，得到目标产物4-[5-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)哌啶-2-基]哌嗪-1-羧酸叔丁酯（90c），为白色固体（80.0g，收率56%）。质谱（LCMS，ESI正离子模式）：计算值C20H32BN3O4 [M+H]+ 390.2，实测值390.2。
参考文献：
[1] Patent: US2014/364414, 2014, A1. Location in patent: Paragraph 0945; 0950-0951
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5361 - 5379
[3] Patent: US2013/225548, 2013, A1. Location in patent: Paragraph 0531; 0632
[4] Patent: CN104650049, 2018, B. Location in patent: Paragraph 0426; 0427
知名试剂公司产品信息
Alfa Aesar
6-(4-Boc-1-哌嗪并)吡啶-3-硼酸频哪醇酯6-(4-Boc-1-piperazinyl)pyridine-3-boronic acid pinacol ester(496786-98-2)
Sigma Aldrich
496786-98-2(sigmaaldrich)