2-methylsulfanyl-butyraldehyde | 132331-36-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylsulfanyl-butyraldehyde
• 英文别名: 2-Methylsulfanylbutanal
• CAS: 132331-36-3
• 化学式: C₅H₁₀OS
• 分子量: 118.2
• InChiKey: QEBYQXZZQGEKBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylsulfanyl-butyraldehyde 在 硫酸 作用下， 生成 1-甲硫基-2-丁酮
  参考文献：
  名称：

  Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Chlorobutanal 、 sodium thiomethoxide 生成 2-methylsulfanyl-butyraldehyde
  参考文献：
  名称：

  Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730

  摘要：

  DOI：

文献信息

• Duhamel,P. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1972, vol. 274, p. 1233 - 1236
  作者：Duhamel,P. et al.

  DOI：——

  日期：——
• Stereocontrol in the Mukaiyama aldol addition to chiral .alpha.- and .beta.-thio-substituted aldehydes
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi、Emanuela Consolandi

  DOI：10.1021/jo00028a015

  日期：1992.1

  A series of racemic alpha-thio-, beta-thio-, and alpha-methyl-beta-thio-substituted aldehydes has been prepared, and their Lewis acid promoted aldol condensation with nonstereogenic and stereogenic silylketene acetals and silyl enolethers has been studied. With alpha-thio-substituted aldehydes, a high level of non-chelation-controlled diastereofacial selectivity can be easily achieved, while chelation control requires a strongly chelating catalyst and a small, aliphatic S-protecting group. Some examples of addition of stereogenic nucleophiles occurring with efficient diastereofacial syn simple stereoselection are also reported. The reactions of beta-thio-substituted aldehydes are less stereoselective, in particular when the stereocenter is in the beta-position. Models of stereoselection are presented to rationalize the results that were compared with those obtained in similar reactions with chiral alkoxy aldehydes.
• Diastereoselective addition of a silylketene acetal to chiral α-thioaldehydes.
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi

  DOI：10.1016/s0040-4039(00)97160-0

  日期：1990.1
• Diastereoselective cyclocondensation of electron-rich dienes with chiral thio-substituted aldehydes
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi、Laura Raimondi

  DOI：10.1021/jo00039a019

  日期：1992.6

  The Lewis acid-promoted cyclocondensation between two electron -rich dienes with a series of racemic alpha- and beta-thio-substituted aldehydes has been studied. Boron trifluoride etherate proved to be the catalyst of choice, affording satisfactory chemical yields and generally good diastereoselectivities. Other Lewis acidic catalysts gave lower yields and in some cases reversed the sense of the diastereoselection. A rationalization of the stereochemical results is presented.
• Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730
  作者：Kirrmann,A. et al.

  DOI：——

  日期：——