benzaldehyde O-ethyl S-ethyl acetal | 70134-86-0

• 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: benzaldehyde O-ethyl S-ethyl acetal
• 英文别名: α-ethoxy-α-ethylthiotoluene；[Ethoxy(ethylsulfanyl)methyl]benzene
• CAS: 70134-86-0
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: BLXFLVBYYQOTGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzaldehyde O-ethyl S-ethyl acetal 在 高氯酸 、 水 、 盐酸 、 mercury dichloride 作用下， 生成 苯甲醛
  参考文献：
  名称：

  Chemical reactions mediated by heavy metal ions. 1. The mercury(II)-promoted hydrolysis of benzaldehyde O-ethyl S-ethyl acetal

  摘要：

  DOI：

  10.1021/jo00303a013
• 作为产物：
  描述：

  苯甲醛二乙缩醛 在 氯化亚砜 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 benzaldehyde O-ethyl S-ethyl acetal
  参考文献：
  名称：

  Penn, David; Satchell, Derek P. N., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1029 - 1030

  摘要：

  DOI：

文献信息

• Rapid hemiacetal formation from a simple, open-chain monothioacetal during soft metal ion-promoted hydrolysis
  作者：David Penn、Derek P. N. Satchell

  DOI：10.1039/c39820000054

  日期：——

  The Hg2+- and TI3+-promoted hydrolyses of the monothioacetal α-ethoxy-α-ethylthiotoluene (1) proceed via the relatively very rapid formation of the hemiacetal (2) whose subsequent hydrolysis controls the observed rate of aldehyde formation.

  Hg 2+和TI 3+促进的单硫缩醛α-乙氧基-α-乙基硫代甲苯（1）的水解过程通过半缩醛（2）的相对非常快速的形成而进行，其随后的水解控制了所观察到的醛形成速率。
• Aumann, Rudolf; Schroeder, Jochen, Chemische Berichte, 1990, vol. 123, # 10, p. 2053 - 2058
  作者：Aumann, Rudolf、Schroeder, Jochen

  DOI：——

  日期：——
• Chemical reactions mediated by heavy metal ions. 2. Mercury ligation effects on the mercury(II)-promoted hydrolyses of benzaldehyde O-ethyl S-ethyl and S-phenyl acetals
  作者：James L. Jensen、David F. Maynard、Gregory R. Shaw、Tyrrell W. Smith

  DOI：10.1021/jo00033a016

  日期：1992.3

  The kinetics of the mercury(II)-promoted hydrolyses of acyclic O,S-acetals of benzaldehyde have been measured to establish that (i) mercury(II) is a reagent, not a catalyst, in the hydrolysis reaction, (ii) the rate-limiting step can be any of the three steps in Scheme I (k(hemi), k(Hg), or k(acetal)), depending on the concentration of mercury(II) relative to the acid, and (iii) the state of complexation of mercury(II) is critical to its reactivity. Part 1 of this series5 established the ''standard state'' for all further work; this paper utilized the same controls and safeguards. The second-order rate constants for hydrolysis of benzaldehyde O-ethyl S-ethyl acetal promoted by Hg2+, HgCl+, HgBr+, or HgI+ is at the diffusion limit (10(9) M-1 s-1). Rate constants for HgCl2, HgBr2, HgI2, HgCl3-, and HgI3- are 10(6), 10(5), 10(2), 10(4), and 50 M-1 s-1, respectively. Rate constants for hydrolysis of benzaldehyde O-ethyl S-phenyl acetal are the same, within experimental error, except for perhaps the least reactive reagents. Thus, although reagents differ in reactivity by 10(7), the reactivity toward a SEt moiety is equal to the reactivity toward a SPh moiety. A detailed mechanism is presented in which the rate-limiting step does not involve carbon-sulfur bond heterolysis, but rather one of the mercury ligation steps.
• Penn, David; Satchell, Derek P. N., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1029 - 1030
  作者：Penn, David、Satchell, Derek P. N.

  DOI：——

  日期：——
• Chemical reactions mediated by heavy metal ions. 1. The mercury(II)-promoted hydrolysis of benzaldehyde O-ethyl S-ethyl acetal
  作者：James L. Jensen、David F. Maynard

  DOI：10.1021/jo00303a013

  日期：1990.8