α-Methoxy-α-(ethylthio)toluene | 169172-96-7

• 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: α-Methoxy-α-(ethylthio)toluene
• 英文别名: Benzaldehyd-O-methyl-S-ethyl-acetal；[Ethylsulfanyl(methoxy)methyl]benzene
• CAS: 169172-96-7
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: VIFRFRFKYVBGMO-UHFFFAOYSA-N

物化性质

• 沸点：
  228.4±28.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  α-Methoxy-α-(ethylthio)toluene 在 烯丙基三丁基锡 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-chloro-4-phenyl-1-butene
  参考文献：
  名称：

  Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

  摘要：

  On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides. This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated; or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used. In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of(O,S) mixed acetals are-interpreted in terms of two major factors operating in opposite directions. H-1 NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed. However, because of the much stronger C-O bond as compared to the C-Se bond, this latter.(also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products. In contrast with BF3 . OEt(2), boron trichloride and boron tribromide were found to react with (O,Se) acetals to give the corresponding alpha-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

  DOI：

  10.1021/jo00124a029
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 乙硫醇 在 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 25.0h， 以68%的产率得到α-Methoxy-α-(ethylthio)toluene
  参考文献：
  名称：

  溴化锂，一种在温和反应条件下用于缩醛单硫缩醛化的新型高效催化剂

  摘要：

  溴化锂在温和反应条件下作为催化剂对醛的单硫醇缩合反应非常有效，能够以优异的产率和高的化学选择性提供反应产物。

  DOI：

  10.1055/s-2001-17477

文献信息

• Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane
  作者：Bernard Hermans、Laszlo Hevesi

  DOI：10.1021/jo00124a029

  日期：1995.9

  On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides. This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated; or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used. In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of(O,S) mixed acetals are-interpreted in terms of two major factors operating in opposite directions. H-1 NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed. However, because of the much stronger C-O bond as compared to the C-Se bond, this latter.(also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products. In contrast with BF3 . OEt(2), boron trichloride and boron tribromide were found to react with (O,Se) acetals to give the corresponding alpha-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.
• Lithium Bromide, a Novel and Highly Effective Catalyst for Monothioacetalization of Acetals under Mild Reaction Conditions
  作者：Fumiaki Ono、Ryojyu Negoro、Tsuneo Sato

  DOI：10.1055/s-2001-17477

  日期：——

  Lithium bromide is efficient as a catalyst for the monothioacetalization of acetals under mild reaction conditions to provide products in excellent yields with high chemoselectivity.

  溴化锂在温和反应条件下作为催化剂对醛的单硫醇缩合反应非常有效，能够以优异的产率和高的化学选择性提供反应产物。