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手性4-取代丁内酯类化合物的合成及其结构研究 被引量:6
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作者 王建平 常新红 +1 位作者 田欣哲 陈庆华 《化学学报》 SCIE CAS CSCD 北大核心 2003年第3期411-415,共5页
脂肪族伯胺和伯醇作为亲核试剂 5与 5 L 孟氧基丁烯内酯 ( 4)手性合成子通过不对称Michael加成 ,得到手性的 4 取代 丁内酯类化合物 6( 44%~ 5 7% ,ee≥ 98% ) .通过元素分析 ,[α] 2 0D ,IR ,1HNMR ,13CNMR ,MS和X射线晶体测定 ,确... 脂肪族伯胺和伯醇作为亲核试剂 5与 5 L 孟氧基丁烯内酯 ( 4)手性合成子通过不对称Michael加成 ,得到手性的 4 取代 丁内酯类化合物 6( 44%~ 5 7% ,ee≥ 98% ) .通过元素分析 ,[α] 2 0D ,IR ,1HNMR ,13CNMR ,MS和X射线晶体测定 ,确认了它们的化学结构、立体构型、绝对构型 . 展开更多
关键词 合成 结构 4-取代丁丙酯 不对称MICHAEL加成 手性合成砌块 X射线晶体测定
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Application of modified amino acid as a chiral building block in asymmetric synthesis 被引量:3
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作者 WANG Jianping ZHANG Xiyun CHEN Qinghua 《Chinese Science Bulletin》 SCIE EI CAS 2001年第23期1952-1956,共5页
Phenylglycine 1 as a representative of natural resourceful a-amino acid was modified by reduction and protection of functional group to afford the amino alcohol as a chiral building block 3. A new chiral compound, the... Phenylglycine 1 as a representative of natural resourceful a-amino acid was modified by reduction and protection of functional group to afford the amino alcohol as a chiral building block 3. A new chiral compound, the chiral building block/spiro-cyclopropane derivative containing four stereogenic centers, compound 7, has been obtained in 52% yield with de≥98% via the tandem double Michael addition/internal nucleophilic substitution under mild condition of 5-l-menthyloxy-3-bromo-2-(5H)-furanone 4 with the nucleophilic reagent, the amino alcohol 3. The new chiral compound 7 is identified on the basis of its analytical data and spectroscopic data, such as UV, IR, 1H NMR, 13C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes 7 was established by X-ray crystallography. This result can provide new route and method for the introduction of chiral building block and the important synthetic strategy in synthesis of some complex molecules containing 展开更多
关键词 MODIFIED α-amino acid PHENYLGLYCINE AMINO alcohol chiral building block spiro-cyclopropane derivative STEREOCHEMISTRY and absolute configuration.
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A New Approach to the Asymmetric Reaction of the Chiron 5-L-Menthyloxy-2(5H)-furanones with Horner-Emmons Reagent 被引量:2
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作者 李学强 王凤荣 +1 位作者 何兰 陈庆华 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2003年第7期805-810,共6页
The asymmetric reaction of the chiron 2(5H)-furanones (4a-4c) with the Homer-Emmons reagents (5a-5b) has been investigated. The newly chiral organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stab... The asymmetric reaction of the chiron 2(5H)-furanones (4a-4c) with the Homer-Emmons reagents (5a-5b) has been investigated. The newly chiral organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stabilized carbanion as a building block in DMSO under mild conditions. Through the asymmetric introduction, the Horner-Emmons reagent could be transformed to a chiral building block to afford the novel functionalized phosphorus derivatives. The structures of the synthesized compounds 6 and 7 were identified on the basis of their elementary and spectroscopic data, such as IR, 1H NMR, 13C NMR, MS and X-ray crystallography. These results provided a valuable approach to the synthesis of potentially interesting chiral organophosphorus derivatives and probing their biological activities. 展开更多
关键词 chiron 2(5H)-furanones asymmetric reaction Horner-Emmons reagent building block chiral organophosphorus derivative biological activity X-ray crystallography
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Concise synthesis of two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids 被引量:2
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作者 ZHENG Xiao1,2,ZHU WenFang1 & HUANG PeiQiang1 1Department of Chemistry,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China 2Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China 《Science China Chemistry》 SCIE EI CAS 2010年第9期1914-1920,共7页
A concise five-step approach to indolizidinones 10 and 11,two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids,has been developed by using N-Cbz pyrrolidin-2-yl pyridin-2-... A concise five-step approach to indolizidinones 10 and 11,two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids,has been developed by using N-Cbz pyrrolidin-2-yl pyridin-2-yl sulfide 13 as the chiral building block.The method features a SmI2-mediated coupling of sulfide 13 with functionalized aldehyde 14 and a tandem N-deprotection-lactamization,which constitutes a stepwise "2 + 4" annulation method for the construction of the indolizidinone ring system of 12a. 展开更多
关键词 indolizidinone SAMARIUM DIIODIDE α-amidohydroxyalkylation TANDEM reaction chiral building block
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一种用于制备生物碱的实用手性砌块的百克级合成方法 被引量:2
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作者 何欢 汪小蓓 宋颢 《华西药学杂志》 CAS CSCD 2019年第3期207-210,共4页
目的设计并合成一种大规模用于制备生物碱的实用手性砌块。方法在有机催化条件下,叔丁基甲基马来酸酯与邻硝基肉桂醛发生不对称Michael加成,随后酸水解脱羧。结果与结论经3步反应(总收率50%)以百克级的规模制备得到手性砌块Ⅰ(96%ee)。
关键词 手性砌块 百克级 有机催化 不对称MICHAEL加成 一锅法脱羧 γ-羰基酯 邻硝基肉桂醛 叔丁基甲基马来酸酯
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Facile and Efficient Synthesis of (R)-4-(Benzyloxy)-3- methylbutanenitrile: Toward Developing a Versatile Chiral Building Block
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作者 宋子杰 史勇 +2 位作者 金荣华 林静容 田伟生 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第10期2595-2597,共3页
A practical synthesis of (R)-4-(benzyloxy)-3-methylbutanenitrile, a potential chiral building block, from the corresponding a-keto ester in high yield and large scale was presented.
关键词 synthetic methods REARRANGEMENT (R)-4-(benzyloxy)-3-methylbutanenitrile chiral building block
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Synthesis of an Antitumoral Diarylheptanoid Containing 1,3-Diol Functionality
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作者 张少敏 伍贻康 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第12期2798-2802,共5页
A bioactive derivative of a natural diarylheptanoid containing a 1,3-anti diol motif was synthesized with the oxygen-carrying stereogenic centers taken from an enantiopure epoxy chiral building block derived from inex... A bioactive derivative of a natural diarylheptanoid containing a 1,3-anti diol motif was synthesized with the oxygen-carrying stereogenic centers taken from an enantiopure epoxy chiral building block derived from inexpensive and readily available D-glucolactone. 展开更多
关键词 natural products DIOL EPOXIDE phenol ETHER chiral building block
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Two Chiral Building Blocks for the Stereocontrolled Synthesis of Anti-and Syn-1,3-Diols
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作者 Yong WU Mei GUAN +2 位作者 Zheng XU Li Cheng Xiao Chun WU 《Chinese Chemical Letters》 SCIE CAS CSCD 2001年第9期765-766,共2页
Two chiral building blocks 1 and 2 for anti-and syn-1, 3-diols has been achieved in 8 steps and 7 steps respectively, starting from the readily available and inexpensive D (+)-xylose 3.
关键词 chiral building block anti-and syn-1 3-diols D (+)-xylose
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Synthesis of an Anti-1,3-Diol Type Chiral Building Block
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作者 Wu, Y Guan, M 《Chinese Chemical Letters》 SCIE CAS CSCD 1998年第11期987-988,共2页
A chiral building block, anti-1,3-diol 2, has been synthesized in 7 steps, starting from readily available and inexpensive D-(+)-xylose.
关键词 chiral building block anti-1 3-Diol D(+)-xylose
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D-葡萄糖衍生的新型多官能团取代手性丁醛的合成
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作者 邓林凤 周骁汉 +1 位作者 秦勇 张丹 《合成化学》 CAS CSCD 2017年第5期403-407,共5页
报道了一种基于D-葡萄糖的多官能团取代手性丁醛的合成方法。以D-葡萄糖为原料,经官能团化和两次高碘酸钠氧化切断策略,合成了一种D-葡萄糖衍生的新型多官能团取代手性丁醛合成子,其结构经1H NMR,13C NMR和LC-MS(ESI)表征。
关键词 D-葡萄糖 多官能团 手性丁醛 手性合成子 合成
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微生物酶合成手性C_3-和C_4-单元
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作者 李祖义 陆秀娟 《有机化学》 SCIE CAS CSCD 北大核心 2003年第11期1236-1240,共5页
具有C3 和C4 单元并含有其它官能团的化合物 ,是合成多种有用化合物很好的原材料 .尤其是光学活性C3 和C4 有机合成单元对制备药物和精细化学产品是非常重要的中间体 .应用具有立体专一性酶的微生物转化过程 ,可不对称合成光学活性物... 具有C3 和C4 单元并含有其它官能团的化合物 ,是合成多种有用化合物很好的原材料 .尤其是光学活性C3 和C4 有机合成单元对制备药物和精细化学产品是非常重要的中间体 .应用具有立体专一性酶的微生物转化过程 ,可不对称合成光学活性物质 .本文阐述了用微生物酶合成手性C3 和C4 单元的最新进展 . 展开更多
关键词 手性砌块 立体专一合成 立体选择降解 微生物转化 微生物酶 有机合成 酶催化
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天然岩藻糖苷酶的抑制剂L-deoxygulojirimycin关键中间体的不对称合成
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作者 魏邦国 陈洁 +1 位作者 林耿杰 黄培强 《厦门大学学报(自然科学版)》 CAS CSCD 北大核心 2006年第5期670-672,共3页
报道一种合成天然氮杂糖L-deoxygulojirimycin关键中间体及全保护L-gulono-1,5-lactam的方法.其关键反应之一为二碘化钐(SmI2)促进下对硅基保护的3-羟基戊二酰亚胺10的C-2位的区域和立体选择性不对称羟甲基化,区域选择性为80 20,立体选... 报道一种合成天然氮杂糖L-deoxygulojirimycin关键中间体及全保护L-gulono-1,5-lactam的方法.其关键反应之一为二碘化钐(SmI2)促进下对硅基保护的3-羟基戊二酰亚胺10的C-2位的区域和立体选择性不对称羟甲基化,区域选择性为80 20,立体选择性为93 7;另一关键反应为采用OsO4-NMO体系对18进行不对称双羟基化反应,立体选择性单一,并通过NOE确定产物的立体化学. 展开更多
关键词 氮杂糖 哌啶 羟甲基化 手性砌块 L-deoxygulojirimycin
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双菌氧化还原耦联转化外消旋2-辛醇制备(R)-2-辛醇
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作者 江娟 徐岩 穆晓清 《化工进展》 EI CAS CSCD 北大核心 2006年第8期947-950,962,共5页
建立了一种新的制备手性2-辛醇的方法——双菌氧化还原耦联转化外消旋2-辛醇制备(R)-2-辛醇。通过筛选得到了一株选择性氧化外消旋2-辛醇中(S)-2-辛醇的菌株CandidacylindraceaATCC14830,其产物的光学纯度e.e.>98%,(R)-2-辛醇的产率&... 建立了一种新的制备手性2-辛醇的方法——双菌氧化还原耦联转化外消旋2-辛醇制备(R)-2-辛醇。通过筛选得到了一株选择性氧化外消旋2-辛醇中(S)-2-辛醇的菌株CandidacylindraceaATCC14830,其产物的光学纯度e.e.>98%,(R)-2-辛醇的产率>46%。与报道的一株还原2-辛酮得到(R)-2-辛醇的菌株OenococcusoeniCECT4730氧化还原耦联,底物浓度可达40g/L,产物的e.e.>98%,产率>92%。 展开更多
关键词 (R)-2-辛醇 柱状假丝酵母 酒明串珠菌 氧化还原耦联 手性化合物
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氨基醇砌块用于螺/环丙环类手性化合物的合成 被引量:7
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作者 王建平 陈庆华 《有机化学》 SCIE CAS CSCD 北大核心 2001年第10期728-731,共4页
手性氨基醇砌块3与5-(l-孟氧基)-3-溴-2(5H)-呋喃酮手性合成子4通过串联的不对称双Michael加成/分子内亲核取代反应,得到了具有四个新的手性中心的氨基醇手性砌块/螺环/环丙烷类化合物7(44%~57%,de≥98%).通过元素分析,[α]20D,UV,IR,1... 手性氨基醇砌块3与5-(l-孟氧基)-3-溴-2(5H)-呋喃酮手性合成子4通过串联的不对称双Michael加成/分子内亲核取代反应,得到了具有四个新的手性中心的氨基醇手性砌块/螺环/环丙烷类化合物7(44%~57%,de≥98%).通过元素分析,[α]20D,UV,IR,1HNMR,13C NMR,MS确认了它们的化学结构.本工作可以为含有某些活性官能团的多手性中心的复杂结构化合物提供新的合成策略. 展开更多
关键词 氨基醇手性砌块 螺环/环丙环类化合物 合成 5-(l-孟氧基)-3-溴-2(5H)-呋喃酮
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由D-Erythorbic Acid合成新的多官能团C_4手性筑块
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作者 李明霞 王言明 陈茹玉 《高等学校化学学报》 SCIE EI CAS CSCD 北大核心 2002年第6期1094-1096,共3页
Compounds 4 and 5 which were new selectively protected and multifunctional chiral C 4 building blocks were prepared conveniently from commercially available D erythorbic acid in no more than three steps with satisfied... Compounds 4 and 5 which were new selectively protected and multifunctional chiral C 4 building blocks were prepared conveniently from commercially available D erythorbic acid in no more than three steps with satisfied yields. Since compound 4 and compound 5 are densely functionalized and rich in stereochemistry, they are useful chiral building blocks in asymmetric synthesis. 展开更多
关键词 合成 多官能团C4手性筑块 D-erythorbicacid 有机合成
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