2-(acetoxymethyl)allyl phenylsulfide | 182312-56-7

• 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-(acetoxymethyl)allyl phenylsulfide
• 英文别名: 2-(Phenylsulfanylmethyl)prop-2-enyl acetate
• CAS: 182312-56-7
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: GOKWUNPRDJAMSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(acetoxymethyl)allyl phenylsulfide 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 六正丁基二锡 作用下， 以 苯 为溶剂， 反应 13.0h， 以72%的产率得到[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-[2-(acetyloxymethyl)prop-2-enyl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  C-Allylation of 1- and 6-Bromosugars with Allylic Sulfides and Sulfones

  摘要：

  Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyranoside (2), and methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranoside (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13, 15, and 16 in 61-90% yield.

  DOI：

  10.1021/jo960749l
• 作为产物：
  描述：

  3-bromo-2-bromomethylpropyl acetate 在 四丁基氟化铵 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.61h， 生成 2-(acetoxymethyl)allyl phenylsulfide
  参考文献：
  名称：

  C-Allylation of 1- and 6-Bromosugars with Allylic Sulfides and Sulfones

  摘要：

  Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyranoside (2), and methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranoside (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13, 15, and 16 in 61-90% yield.

  DOI：

  10.1021/jo960749l

文献信息

• One-pot Synthesis of Allyl Sulfides from Sulfinate Esters and Allylsilanes through Reduction of Alkoxysulfonium Intermediates
  作者：Akihiro Kobayashi、Tsubasa Matsuzawa、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1246/cl.200285

  日期：2020.7.5

  An efficient method to synthesize allyl sulfides from sulfinate esters and allylsilanes is described. Based on the reactivity of isolated allyl(methoxy)phenyl sulfonium triflate, we have developed ...

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