dipropargyl malonate | 71387-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dipropargyl malonate
• 英文别名: dipropargyl manolate；propargyl malonate；Malonsaeure-dipropinylester；Di-2-propinylmalonat；Diprop-2-yn-1-yl propanedioate；bis(prop-2-ynyl) propanedioate
• CAS: 71387-28-5
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: IOUBOIOOGXSGOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  azidoacetonitrile 、 dipropargyl malonate 以 乙醇 为溶剂， 以23%的产率得到bis[(1-cyanomethyl-1,2,3-triazol-4-yl)methyl] malonate
  参考文献：
  名称：

  Synthesis of Polycyclic Functionally-substituted Triazole- and Tetrazole-containing Systems

  摘要：

  Cycloaddition of organic mono- and diazides to the triple bond of propargyl esters of mono- and dicarboxylic acids gave rise to polycyclic 1,2,3-triazole-substituted carboxylates. Dipropargyl dicarboxylates with diazides afforded oligomeric products with alternating triazole and carboxylate fragments. Reaction of a dipropargyl ester with 5-azidomethyltetrazole furnished a tetracyclic system with alternating triazole and tetrazole rings.

  DOI：

  10.1023/b:rujo.0000045898.10072.7f
• 作为产物：
  描述：

  2-丙炔-1-醇 、 丙二酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 dipropargyl malonate
  参考文献：
  名称：

  Regioselective synthesis and antimicrobial studies of ester linked 1,4-disubstituted 1,2,3-bistriazoles

  摘要：

  A series of 1,4-disubstituted 1,2,3-bistriazoles was synthesized via click chemistry by cycloaddition of various bisalkynes with benzyl/2-phenylethyl azide. Synthesized triazoles were characterized by IR, H-1 NMR, C-13 NMR and mass spectral techniques. All the compounds were evaluated for antibacterial/antifungal activities and found to possess moderate to good antimicrobial activities. Further the docking study for the most active compound against DNA Gyrase was also carried out. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.008

文献信息

• Synthesis and properties of new triazole methanofullerenes under the “click-chemistry” conditions
  作者：V. P. Gubskaya、Sh. K. Latypov、F. G. Sibgatullina、A. A. Balandina、T. A. Zhelonkina、G. M. Fazleeva、L. N. Islamova、D. R. Sharafutdinova、I. A. Nuretdinov、O. G. Sinyashin

  DOI：10.1007/s11172-012-0159-6

  日期：2012.6

  The “click-chemistry” methods were used for the first time to synthesize new 1,2,3-triazole derivatives of fullerene, promising for the study of their biological activity, as well as for the preparation of new fullerene-containing materials on their basis. The purity and composition of the compounds synthesized were confirmed by MALDI-TOF mass spectrometry and HPLC, their structures were confirmed by a combination of 2D NMR homo- and heteronuclear correlation.

  该研究首次采用 "点击化学 "方法合成了富勒烯的 1,2,3-三唑新衍生物，为研究其生物活性以及在其基础上制备含富勒烯的新材料带来了希望。通过 MALDI-TOF 质谱法和高效液相色谱法确认了合成化合物的纯度和组成，并结合二维核磁共振同核和异核相关性确认了它们的结构。
• Metathesis of a novel dienediyne system: A unique example involving the usage of in situ generated ethylene as cross-enyne metathesis partner
  作者：Sambasivarao Kotha、Kalyaneswar Mandal

  DOI：10.1016/j.jorganchem.2007.07.009

  日期：2007.10

  A unique example of sequential ring-closing metathesis and cross-enyne metathesis is reported. Here, the in situ generated ethylene by product from ring-closing metathesis is trapped by alkyne moiety. No metathesis product formation was observed with more reactive second generation catalyst in the absence of ethylene. Differential chemoselectivity with the first and second generation Grubbs’ catalyst

  报道了顺序闭环复分解和跨烯炔复分解的独特实例。在此，来自闭环复分解的原位产生的乙烯副产物被炔部分捕获。在没有乙烯的情况下，使用反应性更高的第二代催化剂未观察到易位产物的形成。当在乙烯的外部来源存在下进行反应时，已经观察到第一代和第二代格鲁布斯催化剂的化学选择性不同。
• Synthesis of Polyether Cyclophanes through Rhodium-Catalyzed Cross-Alkyne Cyclotrimerization
  作者：Ken Tanaka、Hiromi Sagae、Kazuki Toyoda、Keiichi Noguchi

  DOI：10.1002/ejoc.200600232

  日期：2006.8

  complex give [7]–[21]polyether cyclophanes in good yield. [8]–[9]Ester cyclophanes were also synthesized from the corresponding α,ω-diynes. The ratio of para-, meta-, and orthocyclophanes depends on the length and the structure of the α,ω-diyne tether chain, whilst the effect of concentration on the yield of polyether cyclophanes appears to be small. X-ray analysis revealed that a single crystal of [15]metacyclophane

  在催化量的阳离子铑 (I)/H8-BINAP 配合物存在下，醚连接的 α,ω-二炔和乙炔二甲酸二甲酯的交叉环三聚反应以良好的收率得到 [7]-[21] 聚醚环芳烃。[8]–[9]酯环芳烃也由相应的α,ω-二炔合成。对-、间-和邻环芳烃的比例取决于 α,ω-二炔系链的长度和结构，而浓度对聚醚环芳烃产率的影响似乎很小。X 射线分析表明，[15]metacyclophane 4g 的单晶是手性形式，[5.5]metacyclophane 4k 的单晶是外消旋形式，因为晶体中没有环翻转。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Reactions of dipropargyl manolate, terephthalate with Co2(CO)8, Mo2Cp2(CO)4 and RuCo2(CO)11 give the di or tetranuclear clusters. The crystal structure of [CH2(CO2CH2C2H-μ)2][Co2(CO)6]2 and [p-(HC2CH2OCO)C6H4(CO2CH2C2H-μ)][Co2(CO)6]
  作者：Yu-Hua Zhang、Wen-Jian Lao、Yue-Qi Liu、Yuan-Qi Yin、Jiang-Jin Wu、Zi-Xiang Huang

  DOI：10.1016/s0277-5387(01)00770-7

  日期：2001.4

  dipropargyl manolate and terephthalate, respectively, with Co2(CO)8 in THF at room temperature gave four new compounds [R(CO2CH2C2H-μ)2][Co2(CO)6]2 (R=CH2, 1a; R=C6H4, 1b) and [(HC2CH2OCO)R(CO2CH2C2H-μ)][Co2(CO)6] (R=CH2, 2a; R=C6H4-1,4-, 2b), and compounds 2a and b reacted with RuCo2(CO)11 to form two new linked clusters [R(CO2CH2C2H-μ)2][Co2(CO)6][RuCo2(CO)9] (R=CH2, 3a; R=C6H4-1,4-, 3b). The treatment of

  摘要室温下，二炔丙基马来酸酯和对苯二甲酸酯与Co2（CO）8在THF中的反应在室温下产生了四个新化合物[R（CO2CH2C2H-μ）2] [Co2（CO）6] 2（R = CH2，1a; R ＝ C6H4，1b）和[（HC2CH2OCO）R（CO2CH2C2H-μ）] [Co2（CO）6]（R ＝ CH2，2a； R ＝ C6H4-1，4-，2b），化合物2a和b反应与RuCo2（CO）11形成两个新的链接簇[R（CO2CH2C2H-μ）2] [Co2（CO）6] [RuCo2（CO）9]（R = CH2，3a; R = C6H4-1,4- ，3b）。分别用RuCo2（CO）11处理两种二炔丙基酯可得到另外两个新簇[R（CO2CH2C2H-μ）2] [RuCo2（CO）9] 2（R = CH2，4a; R = C6H4-1， 4-，4b）。马来酸二炔丙基酯，对苯二甲酸酯与Mo2Cp2（CO
• Synthesis and characterization of new rhodium–cobalt mixed-metal octahedral linked clusters containing η2-diyne ligands
  作者：Bao-Hua Zhu、Bin Hu、Wei-Qiang Zhang、Yu-Hua Zhang、Yuan-Qi Yin、Jie Sun

  DOI：10.1016/s0022-328x(03)00630-2

  日期：2003.9

  (13)) in n-hexane at room temperature, respectively. The acetylene moieties of diyne ligands insert into the CoCo bonds of two tetranuclear clusters to give linked octahedral clusters containing two [Rh2Co2C2] units. The structure of cluster 1 was determined by single-crystal X-ray diffraction analysis and all clusters were characterized by elemental analysis (C/H), IR and 1H-NMR spectroscopy.

  六个新RhCo混合金属连接簇配合物的[Rh 2共2（CO）8（μ-CO）2（μ 4，η 2 -HCCCH 2 O）] 2 R（R = C ^ 6 ħ 4 -1,4（1）; C 6 H 4 -1,4（C（O））2（2）;（C（O）CH 2）2（3）;（C（O）CH）2（4）;（C（O））2 CH 2（5）;（C（O））2（6））已从[Rh中的反应合成2共2（CO）12 ]（7）与合适的二炔化合物[（HCCCH 2 CO）] 2 R（R = C ^ 6 ħ 4 -1,4-（8）; C 6 H 4 -1,4（C（O））2（9）;（C（O）CH 2）2（10）;（C（O）CH）2（11）;（C（ O））2 CH 2（12）;（C（O））2（13））在n中己烷分别在室温下。二炔配体的乙炔部分插入两个四核簇的CoCo键中，得到连接的包含两个[Rh 2 Co 2 C 2 ]单元的八面体簇。簇