2-(2'-thiophene)propane-1,3-diol | 131605-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(2'-thiophene)propane-1,3-diol
• 英文别名: 2-(2-thienyl)-1,3-propanediol；2-Thiophen-2-ylpropane-1,3-diol
• CAS: 131605-37-3
• 化学式: C₇H₁₀O₂S
• 分子量: 158.221
• InChiKey: UQAZNVLYPWTGPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2'-thiophene)propane-1,3-diol 在 4-二甲氨基吡啶 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 Acetic acid 3-hydroxy-2-thiophen-2-yl-propyl ester
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3
• 作为产物：
  描述：

  diethyl 2-thienylmalonate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 生成 2-(2'-thiophene)propane-1,3-diol
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3

文献信息

• Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Acyclic 2-Substituted-1,3-Propanediols: A Powerful Entry into Chiral Building Blocks
  作者：Barry M. Trost、Sushant Malhotra、Takashi Mino、Naomi S. Rajapaksa

  DOI：10.1002/chem.200800623

  日期：2008.8.28

  The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized

  描述了使用两性手性双核锌催化剂对内消旋-2-取代-1,3-丙二醇进行不对称酰化。已经证明，通过使用相同的配体家族，2-烷基-和2-芳基-1,3-丙二醇都可以以高产率和对映选择性去对称化。鉴于手性催化剂的两种对映体均可用，去对称产物的两种对映异构体都可以从相同的原料获得。已通过合成几种具有高对映体纯度的手性结构单元证明了去对称化产物的合成效用。
• Desymmetrization of Meso 1,3- and 1,4-Diols with a Dinuclear Zinc Asymmetric Catalyst
  作者：Barry M. Trost、Takashi Mino

  DOI：10.1021/ja029708z

  日期：2003.3.1

  A dinuclear asymmetric zinc catalyst generated by mixing a 2:1 ratio of diethylzinc and 2,6-bis[5-2-diarylhydroxy methyl-1-pyrrolidinyl]-4-methylphenol has been contrasted with enzymes for the desymmetrization of some meso diols. The best ligand has a p-biphenylyl group as the aromatic substituent defining the chiral space. A series of 2-substituted propanediols were examined. The best acyl transfer agent proved to be vinyl benzoate. Diacylation normally did not occur. The phenyl substituted substrate gave 91-95% ee which compares favorably with the best ee of 92% reported for an enzymatic desymmetrization. The methyl substituted substrate gave significantly better results with the dinuclear zinc catalyst (89% yield, 82% ee) as compared to the best enzymatic esterification (70% yield, 60% ee). One case of a 1,4-diol, cis-1,2-bis(hydroxymethyl) cyclohexane, also gave much better results with the dinuclear zinc catalysts (93% yield, 91% ee) as compared to the reported enzymatic process (44% yield, 7% ee). A model to rationalize the results is presented.