2-acetoxy-3-phenoxy-1-propanethiol | 108615-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-acetoxy-3-phenoxy-1-propanethiol
• 英文别名: (1-Phenoxy-3-sulfanylpropan-2-yl) acetate
• CAS: 108615-55-0
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: MRVWCVRDRIMUKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetoxy-3-phenoxy-1-propanethiol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以100%的产率得到2-hydroxy-3-phenoxy-1-propanethiol
  参考文献：
  名称：

  Tolstikov, G. A.; Miftakhov, M. S.; Danilova, N. A., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1082 - 1089

  摘要：

  DOI：
• 作为产物：
  描述：

  thiolester of phenyl glycidyl ether 在 monolithic neat graphene oxide aerogel 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 生成 2-acetoxy-3-phenoxy-1-propanethiol
  参考文献：
  名称：

  Monolithic Neat Graphene Oxide Aerogel for Efficient Catalysis of S → O Acetyl Migration

  摘要：

  Graphene oxide (GO) is highly attractive for catalysis because of its large specific surface area and rich chemical structures. However, it has generally been used as a catalyst carrier. Here, we designed a three-dimensional monolith of neat GO aerogel as a fixed bed carbocatalyst used in the reaction of S -> O acetyl migration for the synthesis of thiol compounds, showing the merits of ultrafast catalytic speed (5-8 h), high selectivity (100%), high yields (near 100%), easy isolation of products, and long -life recyclability (>18 times). Particularly, we achieved for the first time thiol compounds containing functional groups of halogen and hydroxyl, which cannot be synthesized using other currently reported catalysts Control experiments demonstrated that the efficient catalysis mechanism is mainly attributed to the protonic functional groups, ultralarge size, and unpaired electrons of GO, as well as the "cage effect" at nanoscale confined spaces of aerogel cells

  DOI：

  10.1021/acscatal.5b00233

文献信息

• A new synthetic route for the preparation of β-acyloxy mercaptans via the addition of thioacids to epoxides
  作者：Mohammad Abbasi

  DOI：10.1016/j.tetlet.2012.03.045

  日期：2012.5

  A new synthetic route for the preparation of S-benzylated β-acyloxy mercaptans starting from the one-pot reaction of thioacids and epoxides using a silica gel/Et3N combined catalyst is described. The thiol functionality in the crude product is then protected via benzylation and the corresponding thioethers are isolated after chromatography.

  描述了一种新的合成路线，该路线用于使用硅胶/ Et 3 N组合催化剂从硫代酸和环氧化物的一锅反应开始制备S-苄基化β-酰氧基硫醇。然后通过苄基化作用保护粗产物中的硫醇官能度，并在色谱分离后分离出相应的硫醚。
• 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.