CN113292435B - 一种多取代环丁烷化合物的制备方法 - Google Patents

一种多取代环丁烷化合物的制备方法 Download PDF

Info

Publication number
CN113292435B
CN113292435B CN202010109409.2A CN202010109409A CN113292435B CN 113292435 B CN113292435 B CN 113292435B CN 202010109409 A CN202010109409 A CN 202010109409A CN 113292435 B CN113292435 B CN 113292435B
Authority
CN
China
Prior art keywords
compound
unsubstituted
mole
reaction
olefin
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
CN202010109409.2A
Other languages
English (en)
Other versions
CN113292435A (zh
Inventor
吕健
禚彩琪
尚万送
刘永军
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.)
Qingdao University of Science and Technology
Original Assignee
Qingdao University of Science and 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 Qingdao University of Science and Technology filed Critical Qingdao University of Science and Technology
Priority to CN202010109409.2A priority Critical patent/CN113292435B/zh
Publication of CN113292435A publication Critical patent/CN113292435A/zh
Application granted granted Critical
Publication of CN113292435B publication Critical patent/CN113292435B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B01J35/19—
    • B01J35/39—
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • 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
    • B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
    • B01J2231/328—Cycloadditions involving more than 2 components or moieties, e.g. intra-/intermolecualar [2+2+2] or [2+2+1], e.g. Pauson-Khand type
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring

Abstract

本发明公开了属于有机合成技术领域的一种制备多取代环丁烷类化合物的方法。所述方法为：以铱光敏剂和过渡金属RhII为混合催化剂，在蓝光LED灯的照射条件下，将重氮类化合物和烯烃进行[2+2]环加成反应，可直接生成多取代环丁烷类化合物。本发明所述的利用光催化和过渡金属催化重氮类化合物和烯烃的[2+2]环加成反应，制备多取代环丁烷化合物的方法具有科学合理、环境友好、合成方法简单、目标化合物产率高、底物适用性广等特点。

Description

一种多取代环丁烷化合物的制备方法
技术领域
本发明公开了属于有机合成技术领域的一种多取代环丁烷类化合物的制备方法。所述方法为：以铱光敏剂和过渡金属RhII为混合催化剂，在蓝光LED灯的照射下，将重氮类化合物与烯烃进行[2+2]环加成反应，可直接生成多取代环丁烷类化合物。本发明所述的多取代环丁烷化合物的合成方法具有科学合理、环境友好、合成方法简单目标化合物产率高、底物适用性广等特点。
背景技术
可见光诱导的[2+2]环加成反应是一种绿色、高效且环境友好构建环丁烷骨架的合成方法，一直以来吸引了广大化学家的兴趣，。最近，吴骊珠(Angew.Chem.Int.Ed.2017,56,15407-15410)和YOON(J.Am.Chem.Soc.2019,114,9543-9547)等人分别报道了烯烃参与的光诱导[2+2]环加成反应，在该类反应中，他们选取两个相同或不同类型的烯烃作为[2+2]环加成反应的底物。相比于烯烃尤其是不饱和类型的烯烃，重氮类化合物已其反应位点多，活性高等优势，已成为一类十分重要的有机反应中间体。然而到目前为止，有关可见光诱导的重氮化合物与不同类型烯烃的[2+2]环加成反应还未见报道，归其原因可能是重氮化合物容易发生Wolff重排反应而生成环丁酮类化合物。因此，发展一种高效的合成策略来实现可见光催化重氮化合物与烯烃的[2+2]环加成反应显得极为重要，而利用过渡金属和光催化剂的混合催化体系恰好能够实现高效、高选择性制备多取代环丁烷类化合物的目标。
发明内容
本发明提供了一种多取代环丁烷类化合物的制备方法。
一种合成式(I)所示的环丁烷类化合物的制备方法，该方法包括：以铱光敏剂和过渡金属Rh(II)为混合催化剂，在蓝光LED灯的照射条件下，将式(II)所示的重氮类化合物与式(III)所示的烯烃进行[2+2]环加成反应。
Figure BDA0002389435480000021
其中，R1为选自取代或未取代的C1-C10的烷基、取代或未取代的C6-C20的芳基和取代或未取代的杂环基团中的一种；EWG为酯基、氰基、取代或未取代的C6-C20的芳羰基和取代或未取代的C1-C10烷羰基中的一种；R2，R3和R4为各自独立地选自氢、取代或未取代的C1-C5的烷基、取代或未取代的芳基中的一种、酯基、烷氧基和芳巯基中的一种。
优选地，相对于100摩尔份所述的重氮类化合物，烯烃的用量为100-1000摩尔份，优选为100-500摩尔份。
优选地，相对于100摩尔份所述的重氮类化合物，铱光敏剂的用量为0.01-2摩尔份，优选为0.1-1.0摩尔份。
优选地，所述铱光敏剂为式(IV)至(IX)所示化合物中的一种。
Figure BDA0002389435480000022
Figure BDA0002389435480000031
优选地，相对于100摩尔份所述的重氮类化合物，RhII催化剂的用量为0.5-10摩尔份，优选为1-5摩尔份。
优选地，所述的过渡金属RhII催化剂的化学式为Rh2(O2CR5)4，其中，R5为选自取代或未取代的C1-C10的烷基、取代或未取代的C6-C20的芳基和取代或未取代的杂环基团中的一种，优选为乙基。
优选地，所述重氮类化合物与烯烃的[2+2]环加成反应所需的光源为390-456nm的蓝色LED灯，优选为456nm的蓝色LED灯。
优选地，所述α-重氮酸酯化合物与烯烃的[2+2]环加成反应在25-60℃的温度下搅拌进行12-36小时。
优选地，在反应后用石油醚和乙酸乙酯的混合溶剂进行柱层析。
本发明所述的合成多取代环丁烷化合物制备方法具有以下优点：
(1)过渡金属RhII催化与光催化相结合，高效、高选择性且环境友好地合成多取代环丁烷化合物；
(2)相比于不饱和烯烃化合物，重氮化合物具有更加丰富的底物范围、反应活性高等特点；
(3)可以实现更多烯烃底物的参与，如：简单烯烃、1,3-二烯，烯醚、烯硫醚；不饱和烯烃等；
(4)本发明所述的方法易于大规模生产。
附图说明
图1为实施例1制备的化合物3a的NMR图谱；
图2为实施例2制备的化合物3b的NMR图谱；
图3为实施例3制备的化合物3c的NMR图谱；
图4为实施例4制备的化合物3d的NMR图谱；
图5为实施例5制备的化合物3e的NMR图谱；
图6为实施例6制备的化合物3f的NMR图谱。
具体实施方式
下面采用具体的实施例对本发明进一步详细的说明：
下述实施例中所述试验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1
环丁烷类化合物3a的制备，反应方程式如下：
Figure BDA0002389435480000041
在反应瓶中加入化合物1a(100mmol)，化合物2a(500mmol)，Ir(ppy)3(1mmol)，Rh2(OAc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3a，其收率为80％。
3a核磁数据:
1H NMR(500MHz,CDCl3):δ7.30(d,J＝4.0Hz,4H),7.18-7.09(m,7H),6.96(d,J＝7.0Hz,2H),6.88(d,J＝4.0Hz,2H),4.58(d,J＝10.5Hz,1H),4.13-4.03(m,2H),3.51(q,J＝10.0Hz,1H),3.36-3.32(m,1H),2.69(t,J＝11.0Hz,1H),1.18(t,J＝7.0Hz,3H)ppm.
13C NMR(125MHz,CDCl3):δ173.9,150.7,141.5,138.6,128.8,128.6,128.4,127.7,126.7,126.3,126.1,125.9,60.6,54.0,52.7,39.8,34.6,14.2ppm.
实施例2
环丁烷类化合物3b的制备,反应方程式如下：
Figure BDA0002389435480000051
在反应瓶中加入化合物1a(100mmol)，化合物2b(500mmol)，Ir(ppy)3(1mmol)，Rh2(OOc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3b，其收率为60％(3:1d.r.)。
3b核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.34-7.23(m,5H),4.22(d,J＝10.5Hz,1H),4.18-4.13(m,2H),3.78(s,3H),3.44(q,J＝9.5Hz,1H),2.72(t,J＝10.5Hz,1H),2.04(dd,J＝8.5,11.0Hz,1H),1.25(t,J＝7.5Hz,3H),1.05(s,3H)ppm.
13C NMR(125MHz,CDCl3):δ176.8,173.8,137.9,128.2,127.4,126.6,60.7,52.1,48.0,44.2,36.0,32.1,18.6,14.2ppm.
实施例3
环丁烷类化合物3c的制备,反应方程式如下:
Figure BDA0002389435480000052
在反应瓶中加入化合物1a(100mmol)，化合物2c(500mmol)，Ir(ppy)3(1mmol)，Rh2(OAc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3c，其收率为85％(10:1d.r.)。
3c核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.31-7.19(m,10H),4.23-4.16(m,2H),3.69(t,J＝10.0Hz,1H),3.20(t,J＝10.0Hz,1H),2.86(t,J＝9.5Hz,1H),2.25(q,J＝9.5Hz,1H),1.28(t,J＝7.0Hz,3H),1.01-0.95(m,1H),0.51-0.43(m,2H),0.24-0.18(m,2H)ppm.
13C NMR(125MHz,CDCl3):δ171.6,140.2,139.9,126.1,124.8,124.3,124.2,124.2,58.2,47.3,45.5,44.9,43.9,11.9,11.7ppm.
实施例4
环丁烷化合物3d的制备,反应方程式如下:
Figure BDA0002389435480000061
在反应瓶中加入化合物1a(100mmol)，化合物2d(500mmol)，Ir(ppy)3(1mmol)，Rh2(OAc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3c，其收率为69％(3:1d.r.)。
3d核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.32-7.18(m,6.4H),4.90-4.83(m,2.56H),4.16-4.06(m,2.56H),3.93(d,J＝10.5Hz,1H),3.57(d,J＝10.0Hz,0.28H),3.41-3.32(m,1.28H),2.58(dd,J＝9.0Hz,11.5Hz,0.28H),2.34(t,J＝10.0Hz,1H),2.12-2.08(m,0.28H),1.98(dd,J＝8.5Hz,10.5Hz,1H),1.76(s,3H),1.42(s,0.84H),1.25-1.20(m,3.84H),1.07(s,0.84H),1.00(s,3H)ppm.
13C NMR(125MHz,CDCl3):δ174.7,174.7,152.2,147.3,139.7,128.0,128.0,127.8,127.5,126.6,126.3,110.9,108.9,60.5,53.9,49.5,47.2,45.2,37.8,37.0,34.1,21.0,20.9,18.9,14.2ppm.
环丁烷化合物3e的制备,反应方程式如下:
Figure BDA0002389435480000071
在反应瓶中加入化合物1a(100mmol)，化合物2e(500mmol)，Ir(ppy)3(1mmol)，Rh2(OAc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3e，其收率为60％(10:1d.r.)。
3e核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.27-7.25(m,1H),7.20-7.11(m,4H),6.92-6.87(m,3H),6.41(d,J＝7.5Hz,1H),4.22(t,J＝9.0Hz,1H),4.15-4.10(m,2H),4.06(t,J＝7.5Hz,1H),3.33(q,J＝7.5Hz,1H),3.19(dd,J＝16.5,7.5Hz,1H),3.12(dd,J＝10.0,7.5Hz,1H),3.01-2.97(m,1H),1.22(t,J＝7.5Hz,3H)ppm.
13C NMR(125MHz,CDCl3):δ174.7,174.7,152.2,147.3,139.7,128.0,128.0,127.8,127.5,126.6,126.3,110.9,108.9,60.5,53.9,49.5,47.2,45.2,37.8,37.0,34.1,21.0,20.9,18.9,14.2ppm.
环丁烷化合物3e的制备,反应方程式如下:
Figure BDA0002389435480000081
在反应瓶中加入化合物1b(100mmol)，化合物2a(500mmol)，Ir(ppy)3(1mmol)，Rh2(OAc)4(5mmol)，1,2-二氯乙烷(DCE，500mL)，在蓝光LED灯下照射12h。反应结束后，使用旋蒸仪去除反应溶剂，得到粗产物，粗产物经过柱色谱层析分离得到目标产物3f，其收率为65％(2.5:1d.r.)。
3f核磁数据如下:
1H NMR(500MHz,CDCl3):δ7.33-7.20(m,10H),7.12-7.04(m,2.4H),6.94(d,J＝7.0Hz,0.8H),6.89(d,J＝7.0Hz,0.8H),4.11(t,J＝9.0Hz,0.4H),3.91-3.87(m,0.4H),3.75-3.66(m,1.4H),3.56(q,J＝10.0Hz,1H),3.31(q,J＝9.5,1H),2.77-2.71(m,0.4H),2.61-2.53(m,1.4H),2.32(q,J＝10.5Hz,1H),2.10(s,1.2H),2.07(s,3H)ppm.
13C NMR(125MHz,CDCl3):δ174.7,174.7,152.2,147.3,139.7,128.0,128.0,127.8,127.5,126.6,126.3,110.9,108.9,60.5,53.9,49.5,47.2,45.2,37.8,37.0,34.1,21.0,20.9,18.9,14.2ppm.
表一：
Figure BDA0002389435480000091

Claims (7)

1.一种合成式(I)所示的多取代环丁烷化合物的制备方法，该方法包括：以铱光敏剂和过渡金属RhII为混合催化剂，在蓝光LED灯的照射条件下，将式(II)所示的重氮类化合物与式(III)所示的烯烃进行[2+2]环加成反应：
Figure FDA0003620513100000011
其中，所述的铱光敏剂为式(IV)至(IX)所示化合物中的一种：
Figure FDA0003620513100000012
R1为选自未取代的C1-C10的烷基和未取代的C6-C20的芳基中的一种；EWG为乙酯基、氰基、未取代的C6-C20的芳羰基和未取代的C1-C10烷羰基中的一种；R2，R3和R4为各自独立地选自氢、未取代的C1-C5的烷基和未取代的芳基、甲酯基、烷氧基中的一种；过渡金属RhII的化学式为Rh2(O2CR5)4，R5为选自未取代的C1-C10的烷基和未取代的C6-C20的芳基中的一种。
2.根据权利要求1所述的制备方法，其中，相对于100摩尔份所述的重氮类化合物，烯烃的用量为100-1000摩尔份。
3.根据权利要求1所述的制备方法，其中，相对于100摩尔份所述的重氮类化合物，铱光敏剂用量为0.01-2摩尔份。
4.根据权利要求1所述的方法，其中，相对于100摩尔份所述的重氮类化合物，RhII催化剂的用量为0.5-10摩尔份。
5.根据权利要求1所述的方法，其中，所述的重氮类化合物与烯烃的[2+2]环加成反应所需的光源为蓝光LED灯，波长范围为390-456nm。
6.根据权利要求1所述的方法，其中，所述的重氮类化合物与烯烃的[2+2]环加成反应在25-60℃的温度下搅拌进行12-36小时。
7.根据权利要求1所述的方法，其中，在反应后用石油醚和乙酸乙酯的混合溶剂进行柱层析。
CN202010109409.2A 2020-02-22 2020-02-22 一种多取代环丁烷化合物的制备方法 Active CN113292435B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010109409.2A CN113292435B (zh) 2020-02-22 2020-02-22 一种多取代环丁烷化合物的制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010109409.2A CN113292435B (zh) 2020-02-22 2020-02-22 一种多取代环丁烷化合物的制备方法

Publications (2)

Publication Number Publication Date
CN113292435A CN113292435A (zh) 2021-08-24
CN113292435B true CN113292435B (zh) 2022-06-21

Family

ID=77317643

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010109409.2A Active CN113292435B (zh) 2020-02-22 2020-02-22 一种多取代环丁烷化合物的制备方法

Country Status (1)

Country Link
CN (1) CN113292435B (zh)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995012572A1 (en) * 1993-11-04 1995-05-11 Abbott Laboratories Cyclobutane derivatives as inhibitors of squalene synthetase and protein farnesyltransferase

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995012572A1 (en) * 1993-11-04 1995-05-11 Abbott Laboratories Cyclobutane derivatives as inhibitors of squalene synthetase and protein farnesyltransferase

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
2,4-二氧代戊酸甲酯与环(端)烯的[2+2]光环加成反应;张朋等;《烟台大学学报(自然科学与工程版)》;20100115(第01期);全文 *
Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition;Panish, Robert;《Journal of the American Chemical Society》;20130711;第135卷(第25期);第9283-9286页 *
氮杂环丁烷的合成;符志成等;《化学进展》;20180824(第08期);全文 *

Also Published As

Publication number Publication date
CN113292435A (zh) 2021-08-24

Similar Documents

Publication Publication Date Title
Fruit et al. Asymmetric transfer of nitrenes catalyzed by chiral dirhodium (II) using aromatic sulfamate esters
Barkov et al. Highly regio-and stereoselective 1, 3-dipolar cycloaddition of stabilised azomethine ylides to 3, 3, 3-trihalogeno-1-nitropropenes: Synthesis of trihalomethylated spiro [indoline-3, 2′-pyrrolidin]-2-ones and spiro [indoline-3, 3′-pyrrolizin]-2-ones
CN110117260B (zh) 一种3-烷基喹喔啉-2(1h)-酮类化合物的制备方法
Kamlar et al. Formal [3+ 2] cycloaddition of vinylcyclopropane azlactones to enals using synergistic catalysis
Garlets et al. Regio-and stereoselective rhodium (II)-catalyzed C–H functionalization of cyclobutanes
CN114524701B (zh) 一种n-n轴手性吡咯衍生物及其合成方法
Thanh et al. Highly stereoselective intramolecular Buchner reaction of diazoacetamides catalyzed by a Ru (II)–Pheox complex
Li et al. Phosphine-containing Lewis base catalyzed cyclization of benzofuranone type electron-deficient alkenes with allenoates: a facile synthesis of spirocyclic benzofuranones
Liu et al. A highly efficient and eco-friendly method for the synthesis of 1, 3-indandione ring-fused 3-oxindoles bearing two contiguous quaternary stereocenters via an aldol reaction in aqueous media
Cheng et al. Ligand-accelerated palladium (II)-catalyzed enantioselective amination of C (sp2)–H bonds
Lepronier et al. Palladium‐Catalyzed [2+ 1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7‐Membered Carbocycles
CN113292434B (zh) 光催化非芳基重氮化合物和烯烃的环丙烷化反应
CN113292435B (zh) 一种多取代环丁烷化合物的制备方法
Lapuh et al. Late-stage C–H amination of abietane diterpenoids
Basante-Avendaño et al. A Free-Radical and Protecting-Group-Free Approach to (–)-Boschnialactone and γ-Lycorane
Tsou et al. Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones
Song et al. Highly Stereoselective Direct Construction of Diaryl‐Substituted Cyclobutanes
Ge et al. Enantio-and Z-selective synthesis of functionalized alkenes bearing tertiary allylic stereogenic center
Tietze et al. Enantio‐and Diastereoselective Synthesis of Duocarmycine‐Based Prodrugs for a Selective Treatment of Cancer by Epoxide Opening
CN112279765B (zh) 一种手性α-氟代酮化合物的制备方法
US20040236099A1 (en) Intramolecular amidation of sulfamates catalyzed by metalloporphyrins
CN110317170B (zh) 一种3-菲啶基甲酸丙酯类化合物的绿色合成方法
Li et al. Concise total synthesis of (±)-pisiferin
Kowalska et al. Vinylogous Hydrazone Strategy in Stereoselective Synthesis of 2, 3‐Dihydro‐1H‐pyrrolizines–An Organocatalytic, Metal‐Free Route to Ketorolac
Brown et al. Three-component Heck–Diels–Alder cascade processes involving alkylallenes, aryl iodides and dienophiles

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