diethyl (E)-2-(tributylstannyl)fumarate | 6150-36-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl (E)-2-(tributylstannyl)fumarate
• 英文别名: cis-Diethyl-(tri-n-butylstannyl-ethylen)-dicarboxylat；Tri-n-butyl-stannyl-maleinsaeure-diethylester；trans-(C4H9)3SnC(COOC2H5)CHCOOC2H5；2-tributylstannylmaleate；diethyl (Z)-2-tributylstannylbut-2-enedioate
• CAS: 6150-36-3
• 化学式: C₂₀H₃₈O₄Sn
• 分子量: 461.229
• InChiKey: TXONVYYWWBPIKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Bu3Sn(Me)CuCNLi2 、 丁炔二酸二乙酯 在 氯化铵 作用下， 以 not given 为溶剂， 以81%的产率得到diethyl (E)-2-(tributylstannyl)fumarate
  参考文献：
  名称：

  乙炔的苯乙烯-杯化和中间铜酸盐与亲电试剂的反应，作为取代的乙烯基锡烷的合成

  摘要：

  斯坦纳尔-乙炔的加成，然后用各种亲电试剂进行亲电攻击，得到乙烯基锡烷。

  DOI：

  10.1039/c39920000351

文献信息

• Studies in group IV organometallic chemistry
  作者：A.J. Leusink、H.A. Budding、J.W. Marsman

  DOI：10.1016/s0022-328x(00)83730-4

  日期：1967.8

  Organotin monohydrides were brought into reaction with a variety of mono- and disubstituted ethynes. The identity of the resulting products was established by means of elementary analysis, infrared absorption spectroscopy and proton magnetic resonance spectroscopy.

  使有机锡一氢化物与各种单取代和二取代的乙炔反应。通过元素分析，红外吸收光谱和质子磁共振光谱来确定所得产物的身份。
• Ruthenium-Catalyzed<i>trans</i>-Selective Hydrostannation of Alkynes
  作者：Stephan M. Rummelt、Alois Fürstner

  DOI：10.1002/anie.201311080

  日期：2014.4.1

  In contrast to all other transition‐metal‐catalyzed hydrostannation reactions documented in the literature, the addition of Bu3SnH across various types of alkynes proceeds with excellent trans selectivity, provided the reaction is catalyzed by [Cp*Ru]‐based complexes. This method is distinguished by a broad substrate scope and a remarkable compatibility with functional groups, including various substituents

  与文献中记录的所有其他过渡金属催化的锡烷基化反应相反，在各种类型的炔烃中添加Bu 3 SnH具有出色的反式 选择性，前提是该反应被[Cp * Ru]基络合物催化。该方法的特点是具有广泛的底物范围，并且与官能团具有显着的相容性，包括各种取代基，这些取代基既不会在已建立的路易斯酸介导的反式氢化锡的条件下幸存，也无法 承受自由基反应。在不对称炔烃的情况下，适当的催化剂与底物中质子官能团之间的协同作用也可以确保出色的区域选择性。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.4, 1.2.1.1.5.4, page 46 - 51
  作者：

  DOI：——

  日期：——
• Kinetics of the Uncatalyzed Hydrostannation of Diethyl Acetylenedicarboxylate
  作者：John C. Cochran、Kevin L. Caran、Elizabeth A. Pierz、David M. Miller

  DOI：10.1081/sim-120021643

  日期：2003.1.6

  Hydrostannation of carbon-carbon triple bonds is usually catalyzed by a free radical initiator or by metal complexes of palladium, molybdenum or rhodium. However, when the triple bond is substituted with an effective electron-withdrawing group, the addition reaction will proceed in the absence of a catalyst. In this paper we report the kinetics of hydrostannation of diethyl acetylenedicarboxylate, (1), with trimethylstannane (2a), tri-n-propylstannane (2b), tri-n-butylstannane (2c), and triphenylstannane, (2d). Rate constants for these reactants were determined in acetonitrile at 25, 35, and 45 degreesC. Also, rate constants for trimethylstannane and tripropylstannane were determined in cyclohexane and trimethylstannane-d(1) (2e), in acetonitrile. Finally, the hydrostannation with tributylstannane was run at 25, 35, and 45 degreesC in 95% ethanol. Where appropriate, enthalpies and entropies of activation were determined.
• Leusink, A. J.; Marsman, J. W.; Budding, H. A., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 689 - 703
  作者：Leusink, A. J.、Marsman, J. W.、Budding, H. A.

  DOI：——

  日期：——