2-[(3-oxobutyl)sulfanyl]-1-(phenoxymethyl)ethyl acetate | 1383921-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(3-oxobutyl)sulfanyl]-1-(phenoxymethyl)ethyl acetate
• 英文别名: 2-[(3-Oxobutyl)sulfanyl]-1-(phenoxymethyl)ethyl acetate；[1-(3-oxobutylsulfanyl)-3-phenoxypropan-2-yl] acetate
• CAS: 1383921-82-1
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: SSRNZQBMHDISQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯基缩水甘油醚 在 silica gel 、 三乙胺 作用下， 反应 3.08h， 生成 2-[(3-oxobutyl)sulfanyl]-1-(phenoxymethyl)ethyl acetate
  参考文献：
  名称：

  One-pot synthesis of thia-Michael products from thio acids, epoxides, and electron-deficient alkenes promoted by a silica gel/Et3N combined catalyst

  摘要：

  An efficient method for the one-pot production of thia-Michael adducts using thio acids, epoxides, and electron-deficient alkenes is described. Epoxides quickly underwent nucleophilic ring-opening with thio acids on the silica gel surface at room temperature under solvent-free conditions to yield beta-hydroxy thioester intermediates. After addition of an electron-deficient alkene and a catalytic amount of Et3N to the reaction mixture, the beta-acyloxy mercaptans were generated in situ and subsequently underwent thia-Michael addition reactions to produce the corresponding adducts in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.042

文献信息

• Basic Al2O3 promotes one-pot synthesis of thioethers via in situ generation and addition of β-acyloxy mercaptans to electron-deficient alkenes
  作者：Mohammad Abbasi、Dariush Khalili

  DOI：10.1007/s13738-015-0777-7

  日期：2016.4

  Thioethers were synthesized under solvent-free conditions by reacting Michael acceptors with β-acyloxy mercaptans in situ generated from the reaction of epoxides and thioacids in the presence of basic Al2O3 in high yields.

  在无溶剂条件下，通过迈克尔受体与由环氧化物和硫代羧酸在碱性氧化铝存在下反应生成的β-酰氧基硫醇的现场生成物反应，合成了硫醚，产率较高。
• One-pot synthesis of thia-Michael products from thio acids, epoxides, and electron-deficient alkenes promoted by a silica gel/Et3N combined catalyst
  作者：Mohammad Abbasi

  DOI：10.1016/j.tetlet.2012.05.042

  日期：2012.7

  An efficient method for the one-pot production of thia-Michael adducts using thio acids, epoxides, and electron-deficient alkenes is described. Epoxides quickly underwent nucleophilic ring-opening with thio acids on the silica gel surface at room temperature under solvent-free conditions to yield beta-hydroxy thioester intermediates. After addition of an electron-deficient alkene and a catalytic amount of Et3N to the reaction mixture, the beta-acyloxy mercaptans were generated in situ and subsequently underwent thia-Michael addition reactions to produce the corresponding adducts in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.