2-Acetoxy-propan-1-thiol | 35508-06-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Acetoxy-propan-1-thiol
• 英文别名: 1-Mercapto-2-propanol, acetate；1-sulfanylpropan-2-yl acetate
• CAS: 35508-06-6
• 化学式: C₅H₁₀O₂S
• 分子量: 134.199
• InChiKey: QQUPXRYKZXSZAM-UHFFFAOYSA-N

物化性质

• 沸点：
  63 °C(Press: 14 Torr)
• 密度：
  1.040±0.06 g/cm3(Predicted)
• 保留指数：
  906

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Acetoxy-propan-1-thiol 在 N-氯代丁二酰亚胺 作用下， 以47%的产率得到1-chlorosulfanylpropan-2-yl acetate
  参考文献：
  名称：

  Seliger, Hartmut; Goertz, Hans-Helmut, Synthetic Communications, 1980, vol. 10, # 3, p. 175 - 182

  摘要：

  DOI：
• 作为产物：
  描述：

  S-(2-hydroxypropyl) ethanethioate 在 monolithic neat graphene oxide aerogel 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 生成 2-Acetoxy-propan-1-thiol
  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

• Novel triethylamine catalyzed S → O acetyl migration reaction to generate candidate thiols for construction of topological and functional sulfur-containing polymers
  作者：Gang Wang、Li Peng、Yaochen Zheng、Yanqin Gao、Xuedong Wu、Tianhui Ren、Chao Gao、Jin Han

  DOI：10.1039/c4ra09842k

  日期：——

  Various sulphur-containing monomers and polymer materials transformed from different epoxy compounds.

  各种含硫单体及由不同环氧化合物转化而来的聚合物材料。
• 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。
• Lipase-catalyzed chemospecific O-acylation of 3-mercapto-1-propanol and 4-mercapto-1-butanol
  作者：Luis E. Iglesias、Alicia Baldessari、Eduardo G. Gros

  DOI：10.1016/0960-894x(96)00133-3

  日期：1996.4

  The lipase-catalyzed chemospecific O-acylation of 3-mercapto-1-propanol and 4-mercapto-1-butanol by several aliphatic carboxylic acid ethyl esters are described. Similar treatment on 1-mercapto-2-propanol and 3-mercapto-2-butanol did not yield the expected O-acyl derivatives. Copyright (C) 1996 Elsevier Science Ltd
• 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.
• SELIGER H.; GOERTZ H.-H., SYNTH. COMMUN., 1980, 10, NO 3, 175-182
  作者：SELIGER H.、 GOERTZ H.-H.

  DOI：——

  日期：——