dimethyl 2-(trimethylstannyl)maleate | 118631-32-6

• 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: dimethyl 2-(trimethylstannyl)maleate
• 英文别名: dimethyl (E)-2-trimethylstannylbut-2-enedioate
• CAS: 118631-32-6
• 化学式: C₉H₁₆O₄Sn
• 分子量: 306.934
• InChiKey: SLULRPWFDYYVAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  dimethyl 2-(trimethylstannyl)maleate 在 diclazuril 作用下， 以 重水 为溶剂， 生成 2-deuterio-fumaric acid dimethyl ester 、 三甲基氯化锡
  参考文献：
  名称：

  碳甲氧基取代的乙烯基锡烷的原炔基甲酸酯化反应：动力学，立体化学和机理

  摘要：

  DOI：

  10.1021/om00105a036
• 作为产物：
  描述：

  三甲基锡 、 丁炔二酸二甲酯 以 乙腈 为溶剂， 以40-70的产率得到dimethyl 2-(trimethylstannyl)maleate
  参考文献：
  名称：

  碳甲氧基取代的乙烯基锡烷的原炔基甲酸酯化反应：动力学，立体化学和机理

  摘要：

  DOI：

  10.1021/om00105a036

文献信息

• <i>cis</i>-(R‘₂PC₂H₄PR‘₂)PdH(SnR₃) Complexes:  Trapped Intermediates in the Palladium-Catalyzed Hydrostannation of Alkynes
  作者：Roman Trebbe、Frank Schager、Richard Goddard、Klaus-Richard Pörschke

  DOI：10.1021/om9908128

  日期：2000.2.1

  The complexes (R'2PC2H4PR'(2))Pd(C2H4) (R' = Pr-i, Bu-t) react with R3SnH (R = Me, Bu-n) by displacement of the ethene ligand and oxidative addition of the Sn-H bond to generate the chelating phosphane stabilized cis Pd-II hydride stannyl complexes (R'2PC2H4PR'(2))PdH(SnR3) (R' = Pr-i (1), Bu-t (2)). Complex 1a (R' = Pr-i, R = Me), containing the smallest substituents, is only transiently formed but has been detected at -80 degrees C by NMR spectroscopy. It reacts further with Me3SnH, even at -120 degrees C, by eliminating hydrogen to give (d(i)ppe)Pd(SnMe3)(2) (3). In contrast, the isolated (d(i)ppe)PdH((SnBu3)-Bu-n) (Pb) is briefly stable at ambient temperature, whereas the sterically encumbered species (d(t)bpe)PdH(SnR3) (R = Me (2a), Bu-n (2b)) are stable well above 100 degrees C. The molecular structure of 2a has been determined by X-ray crystallography. Complex 2a reacts with 2 equiv of C2R "(2) (R " = CO2Me) to give (d(t)bpe)Pd(C2R "(2)) (4) and predominantly the corresponding (E)-vinylstannane (E)-(R ")(H)C=C(SnMe3)(R ") (E-5). Since 2a also catalyzes the hydrostannation of the alkyne, the cis Pd-II hydride stannyl complexes 1a,b and 2a,b represent trapped intermediates in the Pd-catalyzed hydrostannation of alkynes. The existence of the complexes also sheds light on the mechanism of the Pd-catalyzed degradation of R3SnH into Sn2R6 and H-2.