2,4,6-Tristhiobenzaldehyde | 157981-88-9

• 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: 2,4,6-Tristhiobenzaldehyde
• 英文别名: 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehyde；2,4,6-tris[bis(trimethylsilyl)methyl]thiobenzaldehyde
• CAS: 157981-88-9
• 化学式: C₂₈H₆₀SSi₆
• 分子量: 597.363
• InChiKey: KYOQQCQKERAPNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.55
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-Tristhiobenzaldehyde 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 [1-[2,4,6-Tris-(bis-trimethylsilanyl-methyl)-phenyl]-meth-(E)-ylidene]-hydrazine
  参考文献：
  名称：

  Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes

  摘要：

  AbstractThe first rotational isomers of thiobenzaldehydes, TbtCHS (2a and 2b; Tbt = 2,4,6‐tris[bis(trimethylsilyl)methyl]phenyl), were synthesized and isolated as stable crystalline compounds by the desulfurization of the corresponding overcrowded cyclic polysulfides TbtCHSn (n = 5 or 8) with phosphine reagents. The molecular structures of 2a and 2b in the solid state, determined by X‐ray crystallographic analysis, differed in their conformations, which were essentially identical with those in solution as revealed by 1H{1H} nuclear Overhauser effect (NOE) experiments. The isomeric thiobenzaldehydes 2a and 2b were found to undergo thermal interconversion. A kinetic study of this process gave reasonable kinetic and thermodynamic parameters for conformational isomerizations of this type. Interesting differences in reactivity among the two isomers 2a,b and 2,4,6‐tri‐tert‐butylthiobenzaldehyde (1) were shown in the reactions with hydrazine and m‐chloroperoxybenzoic acid.

  DOI：

  10.1002/chem.19970030111
• 作为产物：
  描述：

  2,4,6-Trisphenylpentathiane 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以89%的产率得到2,4,6-Tristhiobenzaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes

  摘要：

  AbstractThe first rotational isomers of thiobenzaldehydes, TbtCHS (2a and 2b; Tbt = 2,4,6‐tris[bis(trimethylsilyl)methyl]phenyl), were synthesized and isolated as stable crystalline compounds by the desulfurization of the corresponding overcrowded cyclic polysulfides TbtCHSn (n = 5 or 8) with phosphine reagents. The molecular structures of 2a and 2b in the solid state, determined by X‐ray crystallographic analysis, differed in their conformations, which were essentially identical with those in solution as revealed by 1H{1H} nuclear Overhauser effect (NOE) experiments. The isomeric thiobenzaldehydes 2a and 2b were found to undergo thermal interconversion. A kinetic study of this process gave reasonable kinetic and thermodynamic parameters for conformational isomerizations of this type. Interesting differences in reactivity among the two isomers 2a,b and 2,4,6‐tri‐tert‐butylthiobenzaldehyde (1) were shown in the reactions with hydrazine and m‐chloroperoxybenzoic acid.

  DOI：

  10.1002/chem.19970030111

文献信息

• Synthesis and Structure of 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehyde: The First Isolation of Rotational Isomers of Thiobenzaldehydes
  作者：Norihiro Tokitoh、Nobuhiro Takeda、Renji Okazaki

  DOI：10.1021/ja00096a062

  日期：1994.8
• Tokitoh, Norihiro; Takeda, Nobuhiro; Okazaki, Renji, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 389 - 390
  作者：Tokitoh, Norihiro、Takeda, Nobuhiro、Okazaki, Renji

  DOI：——

  日期：——
• Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes
  作者：Nobuhiro Takeda、Norihiro Tokitoh、Renji Okazaki

  DOI：10.1002/chem.19970030111

  日期：1997.1

  AbstractThe first rotational isomers of thiobenzaldehydes, TbtCHS (2a and 2b; Tbt = 2,4,6‐tris[bis(trimethylsilyl)methyl]phenyl), were synthesized and isolated as stable crystalline compounds by the desulfurization of the corresponding overcrowded cyclic polysulfides TbtCHSn (n = 5 or 8) with phosphine reagents. The molecular structures of 2a and 2b in the solid state, determined by X‐ray crystallographic analysis, differed in their conformations, which were essentially identical with those in solution as revealed by 1H1H} nuclear Overhauser effect (NOE) experiments. The isomeric thiobenzaldehydes 2a and 2b were found to undergo thermal interconversion. A kinetic study of this process gave reasonable kinetic and thermodynamic parameters for conformational isomerizations of this type. Interesting differences in reactivity among the two isomers 2a,b and 2,4,6‐tri‐tert‐butylthiobenzaldehyde (1) were shown in the reactions with hydrazine and m‐chloroperoxybenzoic acid.