thiolester of phenyl glycidyl ether | 321163-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: thiolester of phenyl glycidyl ether
• 英文别名: S-(2-Hydroxy-3-phenoxypropyl) ethanethioate
• CAS: 321163-40-0
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: UKHUEUZKGZKMJX-UHFFFAOYSA-N

物化性质

• 沸点：
  375.0±32.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  苯基缩水甘油醚 、 硫代乙酸 在 β-环糊精 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以90%的产率得到thiolester of phenyl glycidyl ether
  参考文献：
  名称：

  β-环糊精存在于水中的环氧乙烷与硫代酸的有效区域选择性开环

  摘要：

  摘要 在室温下，在 β-环糊精的存在下，通过使用硫代乙酸和硫代苯甲酸对环氧乙烷进行区域选择性开环，实现了温和而方便的 β-羟基硫酯合成。β-羟基硫酯的收率很高，β-环糊精也可以回收再利用。IICT 通讯第 060302 号。

  DOI：

  10.1080/00397910600775572

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。
• チオール化合物の製造方法
  申请人：日本ペイント株式会社

  公开号：JP2005075746A

  公开（公告）日：2005-03-24

  PROBLEM TO BE SOLVED: To provide a method for producing a thiol compound without using hydrogen sulfide.

  SOLUTION: This method for producing the thiol compound comprises a process for reacting an epoxy group-having epoxy compound with a thiocarboxylic acid to obtain the thiol ester, and a process for hydrolyzing the obtained thiol ester to obtain the thiol compound. The epoxy compound may be a compound having at least two epoxy groups, such as polyglycidyl ether or an epoxy resin. The molar ratio of the epoxy groups of the epoxy compound to the thiocarboxy group of the thiocarboxylic acid may be 20/80 to 45/55.

  COPYRIGHT: (C)2005,JPO&NCIPI

  问题要解决的是：提供一种不使用硫化氢生产硫醇化合物的方法。 解决方案：该生产硫醇化合物的方法包括以下步骤：将含环氧基的环氧化合物与硫代羧酸反应以获得硫醇酯，再水解所得的硫醇酯以获得硫醇化合物。环氧化合物可以是具有至少两个环氧基的化合物，例如聚环氧乙烷或环氧树脂。环氧化合物的环氧基与硫代羧基的物质摩尔比可以为20/80至45/55。 版权所有：(C)2005，JPO＆NCIPI
• 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.
• Efficient Regioselective Ring Opening of Oxiranes with Thioacids in the Presence of β‐Cyclodextrin in Water
  作者：B. Srinivas、R. Sridhar、K. Surendra、N. Srilakshmi Krishnaveni、V. Pavan Kumar、Y. V. D. Nageswar、K. Rama Rao

  DOI：10.1080/00397910600775572

  日期：2006.11.1

  Abstract A mild and convenient synthesis of β‐hydroxy thioesters has been achieved by the regioselective ring opening of oxiranes using thioacetic acid and thiobenzoic acid in the presence of β‐cyclodextrin in water at room temperature. β‐Hydroxy thioesters are realized in high yields, and β‐cyclodextrin can also be recovered and reused. IICT Communication No. 060302.

  摘要 在室温下，在 β-环糊精的存在下，通过使用硫代乙酸和硫代苯甲酸对环氧乙烷进行区域选择性开环，实现了温和而方便的 β-羟基硫酯合成。β-羟基硫酯的收率很高，β-环糊精也可以回收再利用。IICT 通讯第 060302 号。
• 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