DL-S-acetyl-3-mercaptopropane-1,2-diol | 98975-38-3

• 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: DL-S-acetyl-3-mercaptopropane-1,2-diol
• 英文别名: S-(2,3-dihydroxypropyl) ethanethioate；3-S-Acetyl-3-thio-glycerin；thioacetic acid S-(2,3-dihydroxy-propyl ester)；Thioessigsaeure-S-(2,3-dihydroxy-propylester)
• CAS: 98975-38-3
• 化学式: C₅H₁₀O₃S
• 分子量: 150.199
• InChiKey: XXJMYDJPOTVUFH-UHFFFAOYSA-N

物化性质

• 沸点：
  312.4±32.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DL-S-acetyl-3-mercaptopropane-1,2-diol 在 monolithic neat graphene oxide aerogel 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 acetic acid-(β-hydroxy-β'-mercapto-isopropyl ester)
  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-硫代甘油 、 乙酸酐 以 水 为溶剂， 反应 2.0h， 以43%的产率得到DL-S-acetyl-3-mercaptopropane-1,2-diol
  参考文献：
  名称：

  甘油激酶：底物特异性

  摘要：

  甘油激酶（8.C. 2.7.1.30，ATP：甘油-3-磷酸转移酶）催化 28 个氮、硫和烷基取代的甘油的磷酸化。对 66 种类似物的调查已定性地定义了作为该酶底物可接受性的结构特征。该调查是使用基于 31P NMR 光谱的测定法进行的，该测定法检测甚至通过缓慢反应产生的产物。这些研究表明，甘油激酶接受一系列取代基来代替一个末端羟基（未磷酸化的），并且 C-2 处的氢原子可以被甲基取代。第二个末端羟基（通常被磷酸化的）被其他亲核中心取代通常会导致活性丧失。甘油激酶是合成手性有机物质的有用催化剂，尤其是制备磷脂和类似物的原料。四种微生物（念珠菌属、酵母菌、大肠杆菌和嗜热脂肪芽孢杆菌）的酶动力学常数的比较表明它们之间几乎没有变化。所有磷酸化产物都具有类似于 sn-甘油-3-磷酸酯的立体化学。

  DOI：

  10.1021/ja00310a044

文献信息

• Sjoeberg, Chemische Berichte, 1942, vol. 75, p. 24
  作者：Sjoeberg

  DOI：——

  日期：——
• [EN] ORTHOESTER COMPOSITIONS FOR AFFINITY PURIFICATION OF OLIGONUCLEOTIDES<br/>[FR] COMPOSITIONS D'ORTHOESTER DESTINÉES À LA PURIFICATION PAR AFFINITÉ D'OLIGONUCLÉOTIDES
  申请人：AGILENT TECHNOLOGIES INC

  公开号：WO2019036029A4

  公开（公告）日：2019-04-11
• Glycerol kinase: substrate specificity
  作者：Debbie C. Crans、George M. Whitesides

  DOI：10.1021/ja00310a044

  日期：1985.11

  studies indicate that glycerol kinase accepts a range of substituents in place of one terminal hydroxyl group (that which is not phosphorylated), and that the hydrogen atcm atC-2 can be replaced by a methyl group. Replacement of the second terminal hydroxyl group (that which is normally phosphorylated) by other nucleophilic centers usually results in loss of activity. Glycerol kinase is a useful catalyst

  甘油激酶（8.C. 2.7.1.30，ATP：甘油-3-磷酸转移酶）催化 28 个氮、硫和烷基取代的甘油的磷酸化。对 66 种类似物的调查已定性地定义了作为该酶底物可接受性的结构特征。该调查是使用基于 31P NMR 光谱的测定法进行的，该测定法检测甚至通过缓慢反应产生的产物。这些研究表明，甘油激酶接受一系列取代基来代替一个末端羟基（未磷酸化的），并且 C-2 处的氢原子可以被甲基取代。第二个末端羟基（通常被磷酸化的）被其他亲核中心取代通常会导致活性丧失。甘油激酶是合成手性有机物质的有用催化剂，尤其是制备磷脂和类似物的原料。四种微生物（念珠菌属、酵母菌、大肠杆菌和嗜热脂肪芽孢杆菌）的酶动力学常数的比较表明它们之间几乎没有变化。所有磷酸化产物都具有类似于 sn-甘油-3-磷酸酯的立体化学。
• 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