(+/-)-2-hydroxymethyl-2,5-dihydrothiophene | 74379-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: (+/-)-2-hydroxymethyl-2,5-dihydrothiophene
• 英文别名: 2-hydroxymethyl-2,5-dihydrothiophene；2,5-Dihydro-2-thiophenemethanol；2,5-dihydrothiophen-2-ylmethanol
• CAS: 74379-22-9
• 化学式: C₅H₈OS
• 分子量: 116.184
• InChiKey: OIFYKPGLOQQYBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-hydroxymethyl-2,5-dihydrothiophene 在 吡啶 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 为溶剂， 反应 482.0h， 生成 [(2R,3S,4R)-3,4-dihydroxythiolan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of 1-Deoxy-4-thio-D-ribose starting from Thiophene-2-carboxylic acid

  摘要：

  The de novo synthesis of 1-deoxy-4-thio-D-ribose starting from thiophene-2-carboxylic acid is described, The key step is the cis-dihydroxylation of S-2-acetoxy-2, 5-dihydrothiophene, which is obtained by enzymatic alcoholysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00290-1
• 作为产物：
  描述：

  Methyl 2,5-Dihydro-2-thiophenecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 (+/-)-2-hydroxymethyl-2,5-dihydrothiophene
  参考文献：
  名称：

  Synthesis of 1-Deoxy-4-thio-D-ribose starting from Thiophene-2-carboxylic acid

  摘要：

  The de novo synthesis of 1-deoxy-4-thio-D-ribose starting from thiophene-2-carboxylic acid is described, The key step is the cis-dihydroxylation of S-2-acetoxy-2, 5-dihydrothiophene, which is obtained by enzymatic alcoholysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00290-1

文献信息

• S-(−)-2-acetoxymethyl-2,5-dihydrothiophene via enzymatic resolution
  作者：Hans-Josef Altenbach、Gerd F Merhof、David J Brauer

  DOI：10.1016/0957-4166(96)00315-1

  日期：1996.9

  For the resolution of (+/-)-2-hydroxymethyl-2,5-dihydrothiophene lipase-catalysed acetylation as well as hydrolysis and alcoholysis of the corresponding acetate were investigated, the best results being obtained in alcoholysis catalysed by lipase from Pseudomonas flurorescens with butanol in organic solvent. Copyright (C) 1996 Elsevier Science Ltd
• Stereoselective synthesis of E-homoallylic alcohols from ?-(dihydro)thienylmethanols
  作者：A. V. Lozanova、A. M. Moiseenkov、A. V. Semenovskii

  DOI：10.1007/bf00949727

  日期：1981.4
• LOZANOVA A. V.; MOISEENKOV A. M.; SEMENOVSKIJ A. V., IZV. AN CCCP. CEP. XIM. 1980, HO 4, 958-959
  作者：LOZANOVA A. V.、 MOISEENKOV A. M.、 SEMENOVSKIJ A. V.

  DOI：——

  日期：——
• Synthesis of 1-Deoxy-4-thio-D-ribose starting from Thiophene-2-carboxylic acid
  作者：Hans-Josef Altenbach、David J. Brauer、Gerd F. Merhof

  DOI：10.1016/s0040-4020(97)00290-1

  日期：1997.4

  The de novo synthesis of 1-deoxy-4-thio-D-ribose starting from thiophene-2-carboxylic acid is described, The key step is the cis-dihydroxylation of S-2-acetoxy-2, 5-dihydrothiophene, which is obtained by enzymatic alcoholysis. (C) 1997 Elsevier Science Ltd.