CN111995544B - 一种4,5-二苯基咪唑啉的合成方法及用途 - Google Patents

一种4,5-二苯基咪唑啉的合成方法及用途 Download PDF

Info

Publication number
CN111995544B
CN111995544B CN202010980763.2A CN202010980763A CN111995544B CN 111995544 B CN111995544 B CN 111995544B CN 202010980763 A CN202010980763 A CN 202010980763A CN 111995544 B CN111995544 B CN 111995544B
Authority
CN
China
Prior art keywords
carried out
reaction
compound
solvent
single crystal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202010980763.2A
Other languages
English (en)
Other versions
CN111995544A (zh
Inventor
罗梅
李国雄
谢蓝
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hefei University of Technology
Original Assignee
Hefei University of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hefei University of Technology filed Critical Hefei University of Technology
Publication of CN111995544A publication Critical patent/CN111995544A/zh
Application granted granted Critical
Publication of CN111995544B publication Critical patent/CN111995544B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

一种有如下结构式的手性化合物合成方法：包括合成、分离和纯化，所述的合成是无水无氧条件下，用催化剂钯配合物1mol％做催化剂，称取偶苯酰0.5mmol及5.0g甲酸铵，放入250mL两口烧瓶中，加入100mL氯苯做溶剂，回流反应30小时后，柱层析分离，用石油醚/二氯甲烷(1/100)洗脱，将收集的最后组分点自然挥发，得单晶4，5‑二苯基咪唑啉：
Figure DDA0002687438720000011
该手性化合物(Ⅰ)的用途，在二苯甲酮亚胺与三甲基硅腈反应中显示了一定的催化效果，其转化率达66％。

Description

一种4,5-二苯基咪唑啉的合成方法及用途
一、技术领域
本发明涉及一种化合物的制备方法及用途，特别涉及一种含氮化合物及其制备方法，确切地说是一种4，5-二苯基咪唑啉的合成方法及用途。
二、背景技术
4，5-二苯基咪唑啉是重要的医药中间体，其合成方法及应用已有文献报道【1-3】
参考文献：
1.Green synthesis of biologically active 2,4,5-trisubstitutedimidazoles catalyzed by large pore zeolite H-BEA through lophine MCRs，Gabla,Jenifer J.et al，Journal of Catalyst&Catalysis,4(3),20-36；2017.
2.Functionalized Diphenyl-Imidazolo-Pyrimidines,Lyubashov,Pavel P.etal,Journal of Heterocyclic Chemistry,55(1),276-281；2018.
3.A mechanistic study of carbonyl activation under solvent-freeconditions:evidence drawn from the synthesis of imidazoles,Pradhan,Kiran etal,RSC Advances,6(13),10743-10749；2016。
三、发明内容
本发明旨在为有机合成领域特别是制备药物中间体提供一种氨基保护的合成方法，所要解决的技术问题是遴选相应的原料并建立相应的方法合成手性药物中间体。
(一)本发明所称的化合物是以下化学式(Ⅰ)所示的化合物：
Figure BDA0002687438700000011
其化学名称：4,5-二苯基咪唑啉。
该化合物(Ⅰ)的合成方法是偶苯酰与甲酸铵在氯苯溶剂中回流反应30小时，
该化学反应式如下：
Figure BDA0002687438700000012
本手性化合物4.5-二苯基咪唑啉的合成方法包括合成、分离和纯化，所述的合成是无水无氧条件下，用催化剂钯配合物1％mol做催化剂，称取偶苯酰0.5mmol及5.0g甲酸铵，放入250mL两口烧瓶中，加入100mL氯苯做溶剂，回流反应30小时后，柱层析分离，用石油醚/二氯甲烷(3/7)洗脱，将收集的最后组分点自然挥发，得单晶4，5-二苯基咪唑啉。该反应的反应机理可推测如下：
偶苯酰在已合成的钯催化剂催化作用下，与甲酸铵作用，首先生成中间体
Figure BDA0002687438700000021
再与甲酸铵产生的CO2作用并进一步的缩合，形成目标化合物。
关于该目标化合物，在2017年，J.O.C曾报道了类似的反应(J.O.C.2017,82,1768-1774)，但是，由于催化剂使用的不同，导致了产品的不同结构。
其作为催化剂在二苯甲酮亚胺与三甲基硅腈反应中显示了一定的催化效果，其转化率达66％。
四、附图说明
图1是4，5-二苯基咪唑啉化合物(I)的单晶衍射图。
五、具体实施方式
1.手性钯配合物的制备
(1)[1,4-(4R)-二异丙基－2－噁唑啉基]苯的制备
在100mL两口瓶中,无水无氧条件下,加入无水ZnCl21.4054g(10.64mmol),40ml氯苯,1,4-二氰基苯5.0236g(39.2mmol),L-缬氨醇16.2075g,将混合物在高温下回流60h,停止反应,减压以除去溶剂,,将剩余物用水溶解,并用CHCl3(20mLx2)萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/二氯甲烷(4:1)柱层析,得浅绿色粘稠状液体,产率52％；白色晶体,熔点:48-50℃,[a]5 D＝+111.9°(c＝0.429,CHCl3)；1HNMR(500MHz,CDCl3,27℃),δ(ppm)＝7.97(s,4H),4.39～4.43(t,3.18Hz,1H),4.09～4.15(m,2H),1.85～1.86(m,1H),(d,J＝6.24Hz,6H),0.86～0.96(d,J＝6.24Hz,6H).13CNMR 18.13,19.03,32.85,70.26,72.76,128.10,128.16,130.32,162.82.IR:3273,2976,2960,2932,2889,2869,1643,1512,1469,1408,1382,1366,1350,1320,1296,1276,1214,1180,1108,1077,1047,1014,971,955,900,891,838,726,698,675,659,540.HRMS(EI):m/z(％):calcd forC18H24N2O2:300.1838；found:300.1833。
(2)双{[1,4-(4S)-二异丙基－2－噁唑啉基苯]氯化钯}配合物的制备
100mL两口瓶中,无水无氧条件下,加入氯化钯1.5603g(4.92mmol),1,4-(4R)-二异丙基－2－噁唑啉基苯1.0435g(3.48mmol)，氯苯30mL将混合物在高温下回流48h,停止反应,减压以除去溶剂,,将剩余物三氯甲烷及乙醇溶解，自然挥发，得红褐色配合物得晶体，产率：92％；m.p.:>200℃,[a]5 D＝+512.8°(c 0.0564,CH3OH)；1H NMR(600MHz,CDCl3),δ`ppm8.81(s,8H,ArH),4.61-4.63(m,4H,CH×4),4.53(t,J＝9.6Hz,4H,CH×4),4.44(t,J＝8.5Hz,4H,CH×4),3.07-3.10(m,4H),1.18 and 1.15(dd,J＝6.7,7.2Hz,24H,CH3×4)；13CNMR(150MHz,CDCl3)δppm 166.8,130.1(×2),129.3,72.0,69.1,30.7,19.0,15.6；νmax(cm-1)3487,3049,2957,2929,2872,1642,1609,1572,1509,1480,1464,1416,1379,1331,1288,1246,1178,1141,1123,1099,1045,1018,959,933,899,854,804,770,722,693,438；Elemental analysis for C36H48N4Cl4O4Pd2,found C 45.26％,H 5.06％,N 5.86％；requires C 45.32％,H 5.24％,N 5.48％；
2. 4，5-二苯基咪唑啉化合物的制备
无水无氧条件下，用催化剂钯配合物1％mol做催化剂，称取偶苯酰0.5mmol及5.0g甲酸铵，放入250mL两口烧瓶中，加入100mL氯苯做溶剂，回流反应30小时后，柱层析分离，用石油醚/二氯甲烷(1/100)洗脱，将收集的最后组分点自然挥发，得单晶4，5-二苯基咪唑啉；元素分析数据C15H12N2，理论值：C：81.79％；H：5.49％；N：12.72％；实测值：C 81.56％；H：5.38％；N：12.49％；EI(C15H13N2):HRMS[m+1/e]：理论值：221.1079；实测值：221.0905.；1HNMR(600MHz,CDCl3,27℃),产率75％；1HNMR(400MHz,CDCl3,27℃),δ(ppm)＝8.0(br,1H),7.64-7.50(m,1H),7.48-7.50(m，4H),7.23-7.30(m，6H),13CNMR(100MHz,CDCl3,27℃)135.1,133.4(x2)，128.2(x4)，127.6(x4),126.8(x4)；IR(KBr):3273,3060，2820，2639，1666，1603，1514，1498，1464，1442，1376，1294，1248，1194，1176，1156，1135，1070，1028，984，955，931，913，877，845，833，778，760，722，673，649，617，567，530；
化合物晶体数据如下：
Figure BDA0002687438700000031
Figure BDA0002687438700000041
晶体典型的键长数据：
Figure BDA0002687438700000042
Figure BDA0002687438700000051
晶体典型的键角数据：
Figure BDA0002687438700000052
Figure BDA0002687438700000061
2.钯配合物的制备
2.1.[1,4-(4R)-二异丙基－2－噁唑啉基]苯的制备
在100mL两口瓶中,无水无氧条件下,加入无水ZnCl21.4054g(mmol),40ml氯苯,1,4-二氰基苯5.0236g(50.75mmol),L-缬氨醇16.2075g,将混合物在高温下回流60h,停止反应,减压以除去溶剂,,将剩余物用水溶解,并用CHCl3(20mLx2)萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/二氯甲烷(4:1)柱层析,得浅绿色粘稠状液体,产率52％；白色晶体,熔点:48-50℃,[a]5D＝+111.9°(c＝0.429,CHCl3)；1HNMR(500MHz,CDCl3,27℃),δ(ppm)＝7.97(s,4H),4.39～4.43(t,3.18Hz,1H),4.09～4.15(m,2H),1.85～1.86(m,1H),(d,J＝6.24Hz,6H),0.86～0.96(d,J＝6.24Hz,6H).13CNMR 18.13,19.03,32.85,70.26,72.76,128.10,128.16,130.32,162.82.IR:3273,2976,2960,2932,2889,2869,1643,1512,1469,1408,1382,1366,1350,1320,1296,1276,1214,1180,1108,1077,1047,1014,971,955,900,891,838,726,698,675,659,540.HRMS(EI):m/z(％):calcd forC18H24N2O2:300.1838；found:300.1833；
2.2双{[1,4-(4S)-二异丙基－2－噁唑啉基苯]氯化钯}配合物的制备
在100mL两口瓶中,无水无氧条件下,加入氯化钯1.5603g(4.92mmol),1,4-(4R)-二异丙基－2－噁唑啉基苯1.0435g(3.48mmol)，氯苯30mL将混合物在高温下回流48h,停止反应,减压以除去溶剂,,将剩余物三氯甲烷及乙醇溶解，自然挥发，得红褐色配合物得晶体，产率：82％；m.p.:>200℃,[a]5 D＝+514.2°(c＝0.0564,CH3OH)：1HNMR(600MHz,CDCl3,27℃),δ(ppm)＝8.86(s,4H),4.56-4.64(m，4H),7.10-7.35(m,6H),5.57(t,J＝0.6Hz,1H)，5.22(t,J＝0.6Hz,1H),4.97(t,J＝0.3Hz,1H),4.46-4.48(m,2H),2.96-2.98(m,2H),1.06-1.12(dd,J＝6.6,7.2Hz,12H)；13CNMR：168.7,132.8,75.2,72.5,33.5,21.5,18.7；元素分析C36H50N4Cl4O5Pd2实测值：C:44.42％,H,5.18％,N,5.76％；计算值：C:44.31％,H,5.14％,N,5.55％；IR:3487,3049,2957,2929，2872,1642,1609,1572,1509,1480,1464,1416,1379,1331,1288,1246,1178,1141,1123,1099,1045,1018,959,933,899,854,804,770,722,693,438；
3.二苯甲酮亚胺与三甲基硅腈的缩合反应应用
Figure BDA0002687438700000071
称取1mmol二苯甲酮亚胺和三甲基硅腈0.2mL放置于25mL小烧瓶中，加入2ml二氯甲烷0.1mmol化合物I，常温下搅拌5h，取少量样品做核磁检测，转化率达:65％；1H NMR(600MHz,CDCl3,27℃)δ7.23–7.59(m,10H),4.10(s,2H)；
另外，发明人在无催化剂条件下进行平行反应，5小时后，其转化率为30％。

Claims (2)

1.一种有如下结构式及晶胞参数的化合物合成方法：包括合成、分离和纯化，所述的合成是无水无氧条件下，用双 {[1,4-(4S)-二异丙基－2－噁唑啉基苯] 氯化钯配合物1%mol做催化剂，称取偶苯酰0.5mmol及5.0g甲酸铵，放入250mL两口烧瓶中，加入100mL氯苯做溶剂，回流反应30小时后，柱层析分离，用石油醚/二氯甲烷（1/100）洗脱，将收集的最后组分点自然挥发，得单晶4，5-二苯基咪唑啉：
Figure QLYQS_1
（I）
该化合物（I）晶体，在296(2) K 温度下，牛津X-射线单晶衍射仪上，用经石墨单色器单色化的MoKα射线（λ=0.71073 Å）以ω-θ 扫描方式收集衍射数据，其特征在于晶体属单斜晶系， P21/C，晶胞参数 ：a = 11.1611(5) Å，α = 90°；b = 9.2699(4) Å ， β = 93.645(2)°；c = 11.8076(6) Å ，γ= 90 °。
2.如权利要求1中化合物（I）的用途，在二苯甲酮亚胺与三甲基硅腈反应中显示了一定的催化效果，其转化率达65%。
CN202010980763.2A 2020-06-30 2020-09-17 一种4,5-二苯基咪唑啉的合成方法及用途 Active CN111995544B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202010614324X 2020-06-30
CN202010614324.XA CN111675629A (zh) 2020-06-30 2020-06-30 一种4,5-二苯基咪唑啉的合成方法及用途

Publications (2)

Publication Number Publication Date
CN111995544A CN111995544A (zh) 2020-11-27
CN111995544B true CN111995544B (zh) 2023-06-16

Family

ID=72437566

Family Applications (2)

Application Number Title Priority Date Filing Date
CN202010614324.XA Withdrawn CN111675629A (zh) 2020-06-30 2020-06-30 一种4,5-二苯基咪唑啉的合成方法及用途
CN202010980763.2A Active CN111995544B (zh) 2020-06-30 2020-09-17 一种4,5-二苯基咪唑啉的合成方法及用途

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN202010614324.XA Withdrawn CN111675629A (zh) 2020-06-30 2020-06-30 一种4,5-二苯基咪唑啉的合成方法及用途

Country Status (1)

Country Link
CN (2) CN111675629A (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112174893B (zh) * 2020-10-15 2023-09-22 合肥工业大学 一种2,4,5-三甲基-1h-咪唑啉甲酸盐的合成方法及用途
CN112225652B (zh) * 2020-11-10 2023-07-25 合肥工业大学 一种二水合四羰基环丁烷化合物的制备及用途
CN112480126B (zh) * 2020-12-11 2022-03-11 合肥工业大学 一种5-烷基喹唑啉衍生物的制备及用途

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1743315A (zh) * 2004-09-03 2006-03-08 首都医科大学 2－取代－4,4,5,5－四甲基－1－羟基咪唑啉，及其合成和应用
CN102875416A (zh) * 2012-10-31 2013-01-16 罗梅 一种手性化合物
CN104326987A (zh) * 2014-10-14 2015-02-04 安徽工业大学 一种水相催化合成2,4,5-三芳基-1h-咪唑衍生物的方法
CN106810533A (zh) * 2016-12-20 2017-06-09 浙江大学 一种手性含亚胺吡啶咪唑啉的化合物及制备方法及金属络合物
CN108658869A (zh) * 2017-03-29 2018-10-16 复旦大学 具有抗肿瘤活性的化合物及其制备方法和在制药中的用途
CN108997242A (zh) * 2018-07-28 2018-12-14 浙江大学 取代苯基吡唑啉酮衍生物及制备和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8455661B2 (en) * 2007-02-18 2013-06-04 University Of Florida Research Foundation, Inc. Catalysts containing N-heterocyclic carbenes for enantioselective synthesis
EP3039740B1 (en) * 2013-11-11 2016-11-09 Lonza Ltd Method for preparation of cyano compounds of the 13th group with a lewis acid

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1743315A (zh) * 2004-09-03 2006-03-08 首都医科大学 2－取代－4,4,5,5－四甲基－1－羟基咪唑啉，及其合成和应用
CN102875416A (zh) * 2012-10-31 2013-01-16 罗梅 一种手性化合物
CN104326987A (zh) * 2014-10-14 2015-02-04 安徽工业大学 一种水相催化合成2,4,5-三芳基-1h-咪唑衍生物的方法
CN106810533A (zh) * 2016-12-20 2017-06-09 浙江大学 一种手性含亚胺吡啶咪唑啉的化合物及制备方法及金属络合物
CN108658869A (zh) * 2017-03-29 2018-10-16 复旦大学 具有抗肿瘤活性的化合物及其制备方法和在制药中的用途
CN108997242A (zh) * 2018-07-28 2018-12-14 浙江大学 取代苯基吡唑啉酮衍生物及制备和应用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Archana S. Gurjar等.In silico studies, synthesis and pharmacological evaluation to explore multi-targeted approach for imidazole analogues as potential cholinesterase inhibitors with neuroprotective role for Alzheimer’s disease.《Bioorganic & Medicinal Chemistry》.2018,第26卷第1511-1522. *
Luo Mei等.Modular Synthesis of Oxazolines and Their Derivatives.《J. Comb. Chem.》.2009,第11卷(第11期),第220-227页. *
Praveen Singh等.Hydrogen bonding framework in imidazole derivatives: Crystal structure and Hirshfeld surface analysis .《European Journal of Chemistry 》.2020,第11卷(第11期),第50-59. *

Also Published As

Publication number Publication date
CN111995544A (zh) 2020-11-27
CN111675629A (zh) 2020-09-18

Similar Documents

Publication Publication Date Title
CN111995544B (zh) 一种4,5-二苯基咪唑啉的合成方法及用途
CN111187219B (zh) 一种磺酰胺咪唑盐化合物及其制备方法和应用
US11840537B2 (en) Preparation and application of a 5-bromoquinazoline derivative
CN112047891B (zh) 一种2-羟基苯基-5-吡嗪基甲酮的合成方法及用途
CN115108930A (zh) 一种氮苯基苯甲酰胺化合物的合成方法及用途
CN112225652B (zh) 一种二水合四羰基环丁烷化合物的制备及用途
Mustafa et al. Silica-based ionic liquid supported on Xanthan [ImSi][PF6]@ xanthan in the synthesis of acridine derivatives by multicomponent reaction
CN114621295B (zh) 一种手性噁唑啉钯配合物晶体及用途
CN112174893B (zh) 一种2,4,5-三甲基-1h-咪唑啉甲酸盐的合成方法及用途
CN112375105B (zh) 一种n,n-配位的含间位碳硼烷配体的二价镍配合物的应用
CN111620808B (zh) 一种2-醛基吲哚类化合物及其制备方法
Sun et al. Synthesis and catalytic activity of heterogeneous rare-earth metal catalysts coordinated with multitopic Schiff-base ligands
CN110314165B (zh) 一种手性噁唑啉钯配合物晶体的用途
US11708373B2 (en) 5-alkylquinazoline derivative, method of preparing the same, and method of using the same
US20220089614A1 (en) Sodium squarate hexahydrate complex
CN113666928A (zh) 一种新型氮原子掺杂于锯齿状边缘的Ovalene-2N的制备方法
CN103467304A (zh) 一种盐酸西那卡塞的制备方法
CN115819288B (zh) 一种腈氧化物、二官能度腈氧化物及其制备方法
CN108484451A (zh) 一种一锅法制备1,2-氨基醇类化合物的方法
CN115286637B (zh) 三氮杂桥环化合物及其中间体化合物、制备方法和应用
CN116003299B (zh) 一种二官能度腈氧化物、制备方法及其应用
CN111848430B (zh) 2-([1,1’-联苯]-4-基)-2-甘氨酸类化合物的合成方法
CN115784941B (zh) 一种三官能度腈氧化物、制备方法及其应用
CN115710214A (zh) 一种Al@SBA-15(2)催化合成1,2-二氢吡啶类化合物的制备方法
CN117551035A (zh) 一种含氮三取代烯烃型化合物及其制备方法和应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant