CAS: 851484-56-5; (3S,4R)-1-(Tert-Butoxycarbonyl)-4-(4-Chlorophenyl)Pyrrolidine-3-Carboxylic Acid

该化合物是一种手性阳性丙烯酸衍生物,具有乙氧基碳基(Boc)保护组和4-氯基替代体.该化合物是有机合成中有价值的中间体,特别是在制药和生物活性分子的制作方面.该有机体组在温酸条件下增强稳定性,促进选择性地减少保护,而3S和4R位置的立体化学确保不对称合成的精确控制.该碳基酸功能允许进一步衍生,使其具有多功能性,可以组合反应.其高纯度和定义明确的立体化学学使其适合医药化学和药物开发的研究.

英文名称(3S,4R)-1-(Tert-Butoxycarbonyl)-4-(4-Chlorophenyl)Pyrrolidine-3-Carboxylic Acid
中文名称(3S,4R)-1-(叔丁氧羰基)-4-(4-氯苯基)吡咯烷-3-羧酸
其它别名N-Boc-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸; Boc-Trans-Dl-B-Pro-4-(4-Chlorophenyl)-Oh
CAS编号851484-56-5
MFCD编号:MFCD28127046
分子式:C16H20ClNO4分子量:325.79
产品CID: 1845634
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: NSBYJYHHDUOADW-QWHCGFSZSA-N
1S/C16H20ClNO4/c1-16(2,3)22-15(21)18-8-12(13(9-18)14(19)20)10-4-6-11(17)7-5-10/h4-7,12-13H,8-9H2,1-3H3,(H,19,20)/t12-,13+/m0/s1
计算化学: 氢键受体数3.0氢键供体数1.0可旋转键数2.0

相似化合物

2459946-49-5 851485-00-2 1227844-81-6

物理性质

沸点465.1±45.0 °C at 760 mmHg
闪点149.2±26.5 °C
密度1.275±0.06 g/cm3(预测)
pKa:4.27±0.40(预测)
PSA:66.84
LogP:3.3751
产品应用该化合物用于制备2H-ISOMINOLIN-1ONES作为强效RHO-KIN酶抑制剂的替代物的中间体.

MSDS等安全信息

警示词warning
危险描述H303 May be harmful if swallowed+H313 Skin contact may be harmful+H333 Inhalation may be harmful to the body
防范说明P264+P280+P305+P351+P338+P337+P313
安全声明H303+H313+H333

上下游产品

1-tert-butyl 3-methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-1,3-dicarboxylate tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(4-chlorophenyl)pyrrolidine-1-carboxylate tert-butyl (3R,4S)-3-(4-chlorophenyl)-4-{[(3R,4R,5S)-4-hydroxy-3,5-dimethyl-4-phenylpiperidin-1-yl]carbonyl}pyrrolidine-1-carboxylate methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-carboxylate

合成工艺路线路线简述

合成目标产物 Boc-Trans-Dl-B-Pro-4-(4-Chlorophenyl)-Oh 主要起始原料 (3S,4R)-4-(4-Chlorophenyl)-1,3-Pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl)3-Methyl Ester
(文献来源)合成步骤主要原料 (3S,4R)-4-(4-Chlorophenyl)-1,3-Pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl)3-Methyl Ester

📜Tert-Butyl (3S,4R)-3-{[(4R)-4-Benzyl-2-Oxo-1,3-Oxazolidin-3-Yl]Carbonyl}-4-(4-Chlorophenyl)Pyrrolidine-1-Carboxylate置于lithium Hydroxide,双氧水体系中,化学反应 2.0H,以96%的收率获得产物n-Boc-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸
参考文献:Synthesis And Characterization Of Pyrrolidine Derivatives As Potent Agonists Of The Human Melanocortin-4 Receptor
标题:Synthesis And Characterization Of Pyrrolidine Derivatives As Potent Agonists Of The Human Melanocortin-4 Receptor
摘要:A Series Of Trans-4-Phenylpyrrolidine-3-Carboxamides Were Synthesized And Characterized As Potent Ligands Of The Human Melanocortin-4 Receptor. Interestingly,A Pair Of Diastereoisomers 20F-1 And 20F-2 Displayed Potent Functional Agonist And Antagonist Activity,Respectively. Thus,The 3S,4R-Compound 20F-1 Possessed A K-I Of 11 Nm And An Ec50 Of 24 Nm,While Its 3R,4S-Isomer 20F-2 Exhibited A K-I Of 8.6 And An Ic50 Of 65 Nm. Both Compounds Were Highly Selective Over Other Melanocortin Receptor Subtypes. The Mc4R Agonist 20F-1 Also Demonstrated Efficacy In Diet-Induced Obese Rats. (C) 2007 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Bmcl.2007.09.079