tetra(3-methyl-2-butenyl)stannane

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: tetra(3-methyl-2-butenyl)stannane
• 化学式: C₂₀H₃₆Sn
• 分子量: 395.216
• InChiKey: SFMNJUOUUBCICG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  丙酮酸乙酯 、 tetra(3-methyl-2-butenyl)stannane 在 sodium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 16.0h， 以49%的产率得到ethyl 2-hydroxy-2,3,3-trimethylethyl-4-pentenoate
  参考文献：
  名称：

  A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds

  摘要：

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.

  DOI：

  10.1021/jo015904x

文献信息

• Synthesis and Characterization of Allylic Dihaloboranes
  作者：Stéphanie Le Serre、Jean-Claude Guillemin

  DOI：10.1021/om9706471

  日期：1997.12.1

  Volatile allylic dihaloboranes have been prepared and characterized by H-1, B-11, C-13, and F-19 NMR spectroscopy and mass spectrometry. The stability (tau(1/2)) of such compounds in dilute CDCl3 solutions depends on the substituents and the halides and ranges from a few minutes (allylic dibromoboranes) to several days (allylic difluoroboranes). Allyldihaloborane etherates were obtained by addition of diethyl ether to the corresponding free allyldihaloborane.