dibenzyl 2-(2-propynyl)-2-(2-butynyl)malonate | 1255217-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl 2-(2-propynyl)-2-(2-butynyl)malonate
• 英文别名: Dibenzyl 2-but-2-ynyl-2-prop-2-ynylpropanedioate
• CAS: 1255217-97-0
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: LJWHQRYQGHBWEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  dibenzyl 2-(2-propynyl)-2-(2-butynyl)malonate 、 叔丁基二甲基(2-丙炔氧基)硅烷 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 以69%的产率得到dibenzyl 6-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1H-inden-2,2(3H)-dicarboxylate
  参考文献：
  名称：

  Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations

  摘要：

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。

  DOI：

  10.1055/s-0030-1258521
• 作为产物：
  描述：

  、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以936.1 mg的产率得到dibenzyl 2-(2-propynyl)-2-(2-butynyl)malonate
  参考文献：
  名称：

  Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations

  摘要：

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。

  DOI：

  10.1055/s-0030-1258521

文献信息

• Efficient Generation of Pyridines by Ruthenium Carbene Mediated [2 + 2 + 2] Cyclotrimerization
  作者：Sandra Medina、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1021/ol301498z

  日期：2012.10.5

  Hoveyda–Grubbs’ catalyst is able to catalyze crossed [2 + 2 + 2] cyclotrimerizations of diynes with nitriles. Pyridines are obtained with excellent yields when using activated nitriles and low to moderate yields with nonactivated nitriles which are unreactive under previously described ruthenium catalyzed reaction conditions. Both terminal and internal alkynes give the reaction using this experimental

  Hoveyda–Grubbs的催化剂能够催化二腈与腈的交叉[2 + 2 + 2]环三聚反应。当使用活化的腈时，以优异的产率获得吡啶，而在先前描述的钌催化的反应条件下，未反应的未活化的腈以低至中等的产率获得吡啶。末端炔烃和内部炔烃均使用该实验程序进行反应。
• [2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium–Alkylidene Complexes
  作者：Silvia Alvarez、Sandra Medina、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1021/jo401538p

  日期：2013.10.4

  Ruthenium carbene catalysts are able to catalyze crossed [2+2+2] cyclotrimerizations of alpha,omega-diynes with isocyanates, isothiocyanates, and carbon disulfide. Both aliphatic and aromatic isocyanates can be used to produce fused 2-pyridones, although aliphatic isocyanates were more reactive. Aromatic isocyanates give better results when they bear electron donating substituents. The reaction of unsymmetrical alpha,beta-diynes gave a product only with the substituent adjacent to the 2-pyridone nitrogen. Isothiocyanates gave thiopyranimines upon reaction with the C=S bond, whereas CS2 reacted efficiently to give a thioxothiopyrane.
• Ruthenium Alkylidene-Catalyzed Reaction of 1,6-Heptadiynes with Alkenes
  作者：Silvia Alvarez、Sandra Medina、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1021/jo5028084

  日期：2015.2.20

  Ruthenium carbene catalysts are able to catalyze cross [2 + 2 + 2] cyclotrimerizations of 1,6-diynes with cyclic and acyclic double bonds. A plausible mechanistic competition is described in which electron-deficient alkenes follow similar pathways as those of other ruthenium catalysts previously utilized and produce mixtures of trienes and cyclohexadienes. On the contrary, allylethers give different isomers of the same final products, suggesting that a metathetic cascade pathway operates in these cases.
• Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations
  作者：Javier Pérez-Castells、Álvaro Mallagaray、Sandra Medina、Gema Domínguez

  DOI：10.1055/s-0030-1258521

  日期：2010.9

  Second-generation Grubbs’ catalyst and Hoveyda-Grubbs’ catalyst are able to catalyze both crossed [2+2+2] cyclotrimerization of diynes with alkynes and di- or trimerizations of diynes. Selection of the reaction conditions allows us to favor one particular process. The process is selective when applied to unsymmetric diynes.

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。