(1Z)-1,2-bis(tert-butylsulfanyl)-3-methoxyprop-1-ene | 1236458-59-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1Z)-1,2-bis(tert-butylsulfanyl)-3-methoxyprop-1-ene
• 英文别名: 1,2-Bis(tert-butylsulfanyl)-3-methoxyprop-1-ene；2-[(Z)-2-tert-butylsulfanyl-3-methoxyprop-1-enyl]sulfanyl-2-methylpropane
• CAS: 1236458-59-5
• 化学式: C₁₂H₂₄OS₂
• 分子量: 248.454
• InChiKey: PNZUOFRTZHOYNJ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁基二硫 、 甲基炔丙基醚 在 bis(acetylacetonate)nickel(II) 、 二甲基苯基磷 作用下， 反应 17.0h， 以42%的产率得到(1Z)-1,2-bis(tert-butylsulfanyl)-3-methoxyprop-1-ene
  参考文献：
  名称：

  Sulfur-containing alkenes—A new class of chelating ligands: Synthesis, coordination to palladium, and structure of the resulting complexes

  摘要：

  Stable 1,2-disulfanylalkene palladium complexes [(RS-CH=CR'-SR)PdCl2] were synthesized in 85-94% yield by reaction of palladium(II) chloride with sulfur-containing ligands RS-CH=C(R')-SR (analogs of dithiolate ligands). The structure of the complexes was studied by NMR spectroscopy and quantum-chemical methods. The binding energy in palladium complexes with bis(arylsulfanyl)- and bis(alkylsulfanyl)alkenes was estimated (DFT) at 50 and 56 kcal/mol, respectively. Variation of substituents on the sulfur atoms is a convenient tool for fine tuning of the ligand properties and controlling the strength of the complex. The bite angle of the ligands does not depend on the substituent nature and is 88-89 degrees, which is typical of square-planar complexes. According to the bite angle, the examined ligands are analogs of well known bidentate phosphine ligands, but the former are more labile since the corresponding binding energy is lower by 36 kcal/mol.

  DOI：

  10.1134/s107042800912001x

文献信息

• Sulfur-containing alkenes—A new class of chelating ligands: Synthesis, coordination to palladium, and structure of the resulting complexes
  作者：V. P. Ananikov、A. O. Piroyan、K. A. Gaiduk、I. P. Beletskaya、V. N. Khrustalev、M. Yu. Antipin

  DOI：10.1134/s107042800912001x

  日期：2009.12

  Stable 1,2-disulfanylalkene palladium complexes [(RS-CH=CR'-SR)PdCl2] were synthesized in 85-94% yield by reaction of palladium(II) chloride with sulfur-containing ligands RS-CH=C(R')-SR (analogs of dithiolate ligands). The structure of the complexes was studied by NMR spectroscopy and quantum-chemical methods. The binding energy in palladium complexes with bis(arylsulfanyl)- and bis(alkylsulfanyl)alkenes was estimated (DFT) at 50 and 56 kcal/mol, respectively. Variation of substituents on the sulfur atoms is a convenient tool for fine tuning of the ligand properties and controlling the strength of the complex. The bite angle of the ligands does not depend on the substituent nature and is 88-89 degrees, which is typical of square-planar complexes. According to the bite angle, the examined ligands are analogs of well known bidentate phosphine ligands, but the former are more labile since the corresponding binding energy is lower by 36 kcal/mol.