S-(2-hydroxybutyl) ethanethioate | 344323-17-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-(2-hydroxybutyl) ethanethioate
• CAS: 344323-17-7
• 化学式: C₆H₁₂O₂S
• 分子量: 148.226
• InChiKey: CNCYAUUNSQINHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(2-hydroxybutyl) ethanethioate 在 monolithic neat graphene oxide aerogel 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 生成 1-mercapto-2-acetoxybutane
  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
• 作为产物：
  描述：

  1,2-环氧丁烷 、 硫代乙酸 以 水 为溶剂， 反应 10.0h， 以93%的产率得到S-(2-hydroxybutyl) ethanethioate
  参考文献：
  名称：

  水中含硫代酸的环氧乙烷的无催化剂有效区域选择性开环

  摘要：

  摘要 在无催化剂条件下，在水存在下研究了硫代乙酸和硫代苯甲酸的环氧化物开环。这种绿色和简单的过程产生了极好的产量。通过简单的滗析，获得高纯度和大规模的产品。在这个过程中，没有观察到烷基卤和酯裂解。

  DOI：

  10.1080/00397911.2010.491172

文献信息

• Catalyst-Free Efficient Regioselective Ring Opening of Oxiranes with Thioacids in Water
  作者：Azim Ziyaei Halimehjani、Aazam Jalali、Maryam Khalesi、Akram Ashouri、Katayoun Marjani

  DOI：10.1080/00397911.2010.491172

  日期：2011.5.3

  Abstract Epoxide ring opening with thioacetic acid and thiobenzoic acid was investigated in the presence of water under catalyst-free conditions. This green and simple process gave an excellent yield. With simple decanting, the products were obtained in high purity and on a large scale. In this process, alkyl halide and ester cleavage were not observed.

  摘要 在无催化剂条件下，在水存在下研究了硫代乙酸和硫代苯甲酸的环氧化物开环。这种绿色和简单的过程产生了极好的产量。通过简单的滗析，获得高纯度和大规模的产品。在这个过程中，没有观察到烷基卤和酯裂解。
• One-Pot Tandem Synthesis of <font>β</font>-Trimethylsilyloxy Thioesters from Thioacids, Epoxides, and HMDS Catalyzed by Silica Gel Under Solvent-Free Conditions
  作者：Mohammad Abbasi

  DOI：10.1080/00397911.2012.667183

  日期：2013.7.3

  A procedure for one-pot preparation of beta-trimethylsilyloxy thioesters from epoxides, thioacids, and hexamethyl disilazane (HMDS) in the presence of silica gel under solvent-free condition was developed. The desired silylated products were isolated in good to excellent yields after silica-gel column chromatography.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• SELIGER H.; GOERTZ H.-H., SYNTH. COMMUN., 1980, 10, NO 3, 175-182
  作者：SELIGER H.、 GOERTZ H.-H.

  DOI：——

  日期：——
• Monolithic Neat Graphene Oxide Aerogel for Efficient Catalysis of S → O Acetyl Migration
  作者：Li Peng、Yaochen Zheng、Jiachen Li、Yu Jin、Chao Gao

  DOI：10.1021/acscatal.5b00233

  日期：2015.6.5

  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