3-(Butylthio)benzenepropanal | 138092-04-3

• 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: 3-(Butylthio)benzenepropanal
• 英文别名: 3-(butylthio)-3-phenylpropanal；3-Butylsulfanyl-3-phenylpropanal
• CAS: 138092-04-3
• 化学式: C₁₃H₁₈OS
• 分子量: 222.351
• InChiKey: LWSDNAFMIUSIFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±30.0 °C(predicted)
• 密度：
  1.025±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-(Butylthio)benzenepropanal 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以50%的产率得到3-(butylthio)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Hydrochalcogenation of activated olefines. Synthesis of functionalized dialkylchalcogenides

  摘要：

  Alkanethiols, selenols and tellurols are generated in situ by reaction of elemental sulfur, selenium and tellurium with commercial alkyllithiums, followed by reaction with deoxygenated water. The alkanechalcogenols react in situ with activated ole. ns in a Michael- type addition reaction. (c) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.06.014
• 作为产物：
  描述：

  3-(isopropylthio)-3-phenylpropanal 在 六氟异丙醇 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 3-(Butylthio)benzenepropanal
  参考文献：
  名称：

  N-杂环卡宾催化的磺胺-迈克尔加成

  摘要：

  已经开发了一种有效的N-杂环卡宾（NHC）催化的烯醛和硫醇之间的磺胺-迈克尔加成（SMA）。在10摩尔％稳定的游离卡宾IPr的催化下，并以20摩尔％的六氟异丙醇（HFIP）作为添加剂，使烯醛与各种硫醇反应，以54-98％的产率提供SMA加合物。在此过程中，游离卡宾通过氢键优先与硫醇相互作用，并且未观察到NHC催化的扩展Umpolung转化。

  DOI：

  10.1039/c7cc07269d

文献信息

• In Situ Generation of <i>n</i>‐Butanethiol and Its Reaction with Electron‐Deficient Olefines
  作者：Rogério A. Gariani、Alcindo A. Dos Santos、João V. Comasseto

  DOI：10.1080/00397910701820897

  日期：2008.2.13

  n-Butanethiol is generated in situ by sequential addition of n-butyllithium and water to elemental sulfur. The n-butanethiol formed was reacted with electron-deficient olefines to give Michael-type addition products in good yields. The method avoids the manipulation of the bad-smelling n-butanethiol.
• 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.