[1]陈 颖,徐崇福,程耀洲,等.2-硝基-2-苄基-1,3-丙二醇的合成[J].常州大学学报(自然科学版),2011,(02):29-31.
 CHEN Ying,XU Chong-fu,CHENG Yao-zhou,et al.Synthesis of 2-Benzyl-2-Nitropropane-1,3-Diol[J].Journal of Changzhou University(Natural Science Edition),2011,(02):29-31.
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2-硝基-2-苄基-1,3-丙二醇的合成()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2011年02期
页码:
29-31
栏目:
出版日期:
2011-03-30

文章信息/Info

Title:
Synthesis of 2-Benzyl-2-Nitropropane-1,3-Diol
作者:
陈 颖徐崇福程耀洲王昕宇张杜鹃
常州大学 石油化工学院,江苏 常州 213164
Author(s):
CHEN YingXU Chong-fuCHENG Yao-zhouWANG Xin-yuZHANG Du-juan
School of Petrochemical Engineering,Changzhou University,Changzhou 213164,China
关键词:
2-硝基-2-苄基-13-丙二醇 羟醛缩合反应 α-丝氨酸 单晶X-射线衍射光谱
Keywords:
2-Benzyl-2-nitropropane-13-diol Aldol condensation α-serines X-ray crystallography
分类号:
O 62.415
文献标志码:
A
摘要:
2-硝基-2-苄基-1,3-丙二醇是合成药物中间体α-丝氨酸的重要先行体,它由β-硝基苯乙烷与三聚甲醛在碱催化条件下的羟醛缩合反应合成。产物通过重结晶得到无色透明晶体,产率49.01%。对去质子剂、反应物配料比、反应温度以及反应时间进行了优化。产物的结构通过1H NMR,13CNMR,IR表征。X-Ray单晶衍射分析揭示分子间和分子内氢键的存在。
Abstract:
2-Benzyl-2-nitropropane-1,3-diol, an importantprecursor for the synthesis of pharmaceutical intermediate α-serines, was synthesized via Aldol condensation of β-nitrophenylethane and s-trioxane in the presence of a base. A transparent crystalline was obtained after recrystallization with 49.01% yield. The selection of deprotonating agents, ratio of the reactants, reaction temperature and reaction time were optimized.The structure of the product was confirmed by 1H NMR,13CNMR and IR spectroscopy. X-ray crystallography revealed the existence of both inter- and intro-molecular hydrogen bonds.

参考文献/References:

[1]Susumi Hatakeyama,Hiromitsu Matsumoto,Hiroko Fukuyama,et al.Et2AlCl-catalyzed cyclization of epoxytrichloroacetimidates for the synthesis of α-substituted serines[J]. Journal of Organic Chemistry,1997, 62(7):2 275-2 279.
[2]Jonathan W Lane,Randall L Halcomb.Anew method for the stereoselective synthesis of α-substituted serine amino acid analogues[J].Organic Letters,2003,5(22):4 017-4 020.
[3]Carda M,Murga J,Castillo E,et al.Stereoselective synthesis of α-substituted serines from protected erythrulose oximes[J].Tetrahedron:Asymmetry,1998,9:1 703-1 712.
[4]Shigeki Sano,Toshio Miwa,Xiao-Kai Liu,et al.Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis ofα-substituted serines[J].Tetrahedron:Asymmetry,1998,9:3 615-3 618.
[5]Shigeki Sano,Takahiro Ishii,Toshio Miwa,et al.Tin-mediated enantioselectivealdol-type reaction for the asymmetric synthesisi of α-substitutedserines utilizing an external chiral ligand,(-)-sparteine[J].Tetrahedron Letters,1999,40:3 013-3 016.
[6]Shigeki Sano,Kazuhiko Hayashi,Toshio Miwa,et al.New enantiodivergent procedure for the syntheses of chiral α-substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis[J].1998,39:5 571-5 574.
[7]马涛,徐文芳,王俊丽,等.AHPA衍生物的设计、合成及抗癌活性研究[J].中国药物化学杂志,2003,13(2):70-75.
[8]Martin Eberle,Martin Egli,Dieter Seebach. Enantioselective saponificationof diacetates of 2-nitro-1,3-propanediols by pig-liver esterase and preparationof enantiomerically pure derivatives of 2-nitroallylic alcohols(chiral multiple-coupling reagents)[J]. Helvetica Chimica Acta,1988, 71(1):1-23.
[9]谭露璐,钱君律,伍艳辉.羟醛缩合催化剂研究进展[J].化学工业与工程,2006, 23(1):70-73.

备注/Memo

备注/Memo:
基金项目:常州大学科技基金资助(ZMF05020022) 作者简介:陈颖(1986-),男,江苏无锡人,硕士生。
更新日期/Last Update: 2011-03-30