4-hydroxymethyl-4-nitro-tetrahydrothiophen-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 4-hydroxymethyl-4-nitro-tetrahydrothiophen-3-ol
• 英文别名: 4-(hydroxymethyl)-4-nitrothiolan-3-ol
• 化学式: C₅H₉NO₄S
• 分子量: 179.197
• InChiKey: ZKHPEBJDPIJCSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 Acetic acid 3-hydroxy-2-nitro-propyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到4-hydroxymethyl-4-nitro-tetrahydrothiophen-3-ol
  参考文献：
  名称：

  Convenient ‘one-pot’ synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael–Henry and Michael–Michael reactions

  摘要：

  In situ generated nitro alkenes underwent tandem Michael-Henry and Michael-Michael sequences leading to the 'one-pot' formation of 3,4-substituted tetrahydrothiophenes using the commercially available 1,4-dithiane-2,5-diol (the dimer of merca-ptoacetaldehyde) or its 4-mercapto-2-butenoates derivatives as suitable bifunctional partners, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.055

文献信息

• 1,4-Dithiane-2,5-diol as an efficient synthon for a straightforward synthesis of functionalized tetrahydrothiophenes via sulfa-Michael/aldol-type reactions with electrophilic alkenes
  作者：Nikla Baricordi、Simonetta Benetti、Valerio Bertolasi、Carmela De Risi、Gian P. Pollini、Francesco Zamberlan、Vinicio Zanirato

  DOI：10.1016/j.tet.2011.10.064

  日期：2012.1

  ‘One-pot’ tandem reactions of commercially available 1,4-dithiane-2,5-diol (the dimer of mercaptoacetaldehyde) with electrophilic alkenes resulted in the facile formation of substituted tetrahydrothiophene derivatives. Thus, sulfa-Michael/Henry and sulfa-Michael/aldol sequences provided polysubstituted tetrahydrothiophenes using in situ generated nitroalkenes and α,β-unsaturated carbonyl compounds

  市售的1,4-二噻吩-2,5-二醇（巯基乙醛的二聚体）与亲电烯烃的“一锅”串联反应可轻松形成取代的四氢噻吩衍生物。因此，sulfa-Michael / Henry和sulfa-Michael / aldol序列分别使用原位生成的硝基烯烃和α，β-不饱和羰基化合物作为巯基乙醛二聚体的亲电子配体提供了多取代的四氢噻吩。
• Convenient ‘one-pot’ synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael–Henry and Michael–Michael reactions
  作者：Achille Barco、Nikla Baricordi、Simonetta Benetti、Carmela De Risi、Gian Piero Pollini

  DOI：10.1016/j.tetlet.2006.09.055

  日期：2006.11

  In situ generated nitro alkenes underwent tandem Michael-Henry and Michael-Michael sequences leading to the 'one-pot' formation of 3,4-substituted tetrahydrothiophenes using the commercially available 1,4-dithiane-2,5-diol (the dimer of merca-ptoacetaldehyde) or its 4-mercapto-2-butenoates derivatives as suitable bifunctional partners, respectively. (c) 2006 Elsevier Ltd. All rights reserved.