(3-Hydroxymethyl-5-methyl-thiophen-2-yl)-methanol | 194161-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (3-Hydroxymethyl-5-methyl-thiophen-2-yl)-methanol
• 英文别名: [2-(Hydroxymethyl)-5-methylthiophen-3-yl]methanol
• CAS: 194161-39-2
• 化学式: C₇H₁₀O₂S
• mdl: MFCD29973957
• 分子量: 158.221
• InChiKey: OWIPGDNBEZONIY-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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：

  (3-Hydroxymethyl-5-methyl-thiophen-2-yl)-methanol 在 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 以88%的产率得到2,3-Bis(bromomethyl)-5-methylthiophene
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392
• 作为产物：
  描述：

  5-甲基-2,3-噻吩二羧酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以77%的产率得到(3-Hydroxymethyl-5-methyl-thiophen-2-yl)-methanol
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392

文献信息

• SYNTHESIS OF THIENO[3,4-b]THIOPHENE, THIENO[3,4-b]FURAN, RELATED COMPOUNDS AND THEIR DERIVATIVES AND USE THEREOF
  申请人：Sotzing Gregory A.

  公开号：US20090326187A1

  公开（公告）日：2009-12-31

  Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

  揭示了制备噻吩并[3,4-b]噻吩、噻吩并[3,4-b]呋喃、相关化合物及其衍生物的廉价且简便的方法。还揭示了由这些融合杂环制备的规则寡聚物。
• US8168671B2
  申请人：——

  公开号：US8168671B2

  公开（公告）日：2012-05-01
• Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).
  作者：Kristin Hammer、Tore Benneche、Håkon Hope、Kjell Undheim、Elemér Fogassy、Charles A. McAuliffe、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0392

  日期：——

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.