3-methyl-2-(methylthio)butanal | 132331-34-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methyl-2-(methylthio)butanal
• 英文别名: 3-methyl-2-methylsulfanylbutanal
• CAS: 132331-34-1
• 化学式: C₆H₁₂OS
• 分子量: 132.227
• InChiKey: NYYIRNKGNOCURL-UHFFFAOYSA-N

物化性质

• 沸点：
  159.6±23.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  3-methyl-2-(methylthio)butanal 在 L-Selectride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 (E)-(2S,5S)-6-Methyl-5-methylsulfanyl-hept-3-en-2-ol
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c
• 作为产物：
  描述：

  异戊酸乙酯 在 lithium aluminium tetrahydride 、 二甲基亚砜 、 二异丙胺 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 3-methyl-2-(methylthio)butanal
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c

文献信息

• Synthesis of Enantiomerically Enriched α-Sulfenylated Ketones and Aldehydes
  作者：Joo-Hack Youn、Rudolf Herrmann、Ivar Ugi

  DOI：10.1055/s-1987-27870

  日期：——

  α-Sulfenylated carbonyl compounds are prepared by the reaction of imines of aldehydes and ketones containing α-hydrogens with disulfides via the metalloenamines. With (R)-α-phenylethylamine as chiral auxiliary, enantiomeric excesses of 13-51% are observed.

  通过含有α-氢的醛和酮的亚胺与二硫化物的反应，利用金属烯胺制备α-硫代羰基化合物。以(R)-α-苯乙胺作为手性辅助剂，观察到13-51%的对映体过量。
• Effects of sulphur nutrition during potato cultivation on the formation of acrylamide and aroma compounds during cooking
  作者：J.S. Elmore、A.T. Dodson、N. Muttucumaru、N.G. Halford、M.A.J. Parry、D.S. Mottram

  DOI：10.1016/j.foodchem.2010.03.049

  日期：2010.10

  Lack of sulphur nutrition during potato cultivation has been shown to have profound effects on tuber composition, affecting in particular the concentrations of free asparagine, other amino acids and sugars. This is important because free asparagine and sugars react at high temperatures to form acrylamide, a suspect carcinogen. Free amino acids and sugars also form a variety of other compounds associated with colour and flavour. In this study the volatile aroma compounds formed in potato flour heated at 180 degrees C for 20 min were compared for three varieties of potato grown, with and without sulphur fertiliser. Approximately 50 compounds were quantified in the headspace extracts of the heated flour, of which over 40 were affected by sulphur fertilisation and/or variety. Many of the 41 compounds found at higher concentrations in the sulphur-deficient flour were Strecker aldehydes and compounds formed from their condensation, whereas only one compound, benzaldehyde, behaved in the same way as did acrylamide and was found at higher concentrations in the sulphur-sufficient flour. The reasons for these effects are discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.