(EZ)-2,2'-Thiobis(acetophenone) bis-oxime

• 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: (EZ)-2,2'-Thiobis(acetophenone) bis-oxime
• 英文别名: (NE)-N-[2-[(2Z)-2-hydroxyimino-2-phenylethyl]sulfanyl-1-phenylethylidene]hydroxylamine
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: BDGMGSWXABXEBE-JRDMOELTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硫化双(苯甲酰甲基) 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (EZ)-2,2'-Thiobis(acetophenone) bis-oxime 、 (ZZ)-2,2'-Thiobis(acetophenone) bis-oxime
  参考文献：
  名称：

  Sulfuranes with Oximate Axial Ligands

  摘要：

  New sulfuranes having one or two axial oximate (R(2)C=NO) ligands were synthesized. An improved sulfurane-forming step, involving a rapidly stirred suspension of NaHCO3, is described. The failure of sulfide oximes in which sulfur bears one or two tertiary carbons to form sulfuranes is explained by a C-S bond cleavage leading to tertiary carbocations. This represents a hitherto unanticipated limitation to the standard method of sulfurane synthesis. The X-ray crystal structure of one of the new sulfuranes, namely 2,2'-spirobi(4-phenyl-3H-1,2,5-oxathiazo is reported (R = 0.0368). An unusual feature was the quite compressed equatorial(C-S-C) angle, 102.6(1)degrees. The S-O bond length, 1.846(2) Angstrom, was similar to S-O bond lengths of sulfuranes having two axial carboxylate ligands. Since the oximate ligand has not been used previously in a 10-S-4 species, an assessment of its apicophilicity relative to other more common axial ligands was made by considering X-ray structural data, IR data, and ab initio calculations. These suggest that the R(2)C=NO ligand is as apicophilic as the hexafluorocumyloxy (ArC(CF3)(2)O) ligand.

  DOI：

  10.1021/jo00118a036

文献信息

• Sulfuranes with Oximate Axial Ligands
  作者：S. F. Hornbuckle、P. Livant、T. R. Webb

  DOI：10.1021/jo00118a036

  日期：1995.6

  New sulfuranes having one or two axial oximate (R(2)C=NO) ligands were synthesized. An improved sulfurane-forming step, involving a rapidly stirred suspension of NaHCO3, is described. The failure of sulfide oximes in which sulfur bears one or two tertiary carbons to form sulfuranes is explained by a C-S bond cleavage leading to tertiary carbocations. This represents a hitherto unanticipated limitation to the standard method of sulfurane synthesis. The X-ray crystal structure of one of the new sulfuranes, namely 2,2'-spirobi(4-phenyl-3H-1,2,5-oxathiazo is reported (R = 0.0368). An unusual feature was the quite compressed equatorial(C-S-C) angle, 102.6(1)degrees. The S-O bond length, 1.846(2) Angstrom, was similar to S-O bond lengths of sulfuranes having two axial carboxylate ligands. Since the oximate ligand has not been used previously in a 10-S-4 species, an assessment of its apicophilicity relative to other more common axial ligands was made by considering X-ray structural data, IR data, and ab initio calculations. These suggest that the R(2)C=NO ligand is as apicophilic as the hexafluorocumyloxy (ArC(CF3)(2)O) ligand.