5-(2,4-dimethylphenyl)-4-nitrotetrahydrothiophen-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2,4-dimethylphenyl)-4-nitrotetrahydrothiophen-3-ol
• 英文别名: (3S,4R,5S)-5-(2,4-dimethylphenyl)-4-nitrothiolan-3-ol
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: LABIZFFRKPEIJM-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二甲基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.25h， 生成 5-(2,4-dimethylphenyl)-4-nitrotetrahydrothiophen-3-ol 、 5-(2,4-dimethylphenyl)-4-nitrotetrahydrothiophen-3-ol
  参考文献：
  名称：

  Tertiary amine functionalized polyacrylonitrile fiber catalyst for the synthesis of tetrahydrothiophenes

  摘要：

  A tertiary amine immobilized fiber was prepared and used to efficiently catalyze tandem Michael-intramolecular Henry reactions between 1,4-dithiane-2,5-diol and trans-beta-nitrostyrenes to form the corresponding tetrahydrothiophene derivatives. This newly developed fiber catalyst is applicable to a wide range of trans-beta-nitroalkenes and affords good to excellent yields (75-93%) under mild conditions (with 2.5 mol % fiber catalyst at 50 C in ethanol for 5 h). The fiber catalyst exhibits excellent recyclability and reusability (up to 10 times) after simple workup procedure with only a slight loss in catalytic activity. It is noteworthy that the major diastereomers have r-R, trans-nitro, trans-hydroxy configurations with diastereoselectivities of up to 15:1. This differs from the results obtained when the same reaction is catalyzed by a homogeneous catalyst. This is the first example of a fiber catalyst exhibiting excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.084

文献信息

• Tertiary amine functionalized polyacrylonitrile fiber catalyst for the synthesis of tetrahydrothiophenes
  作者：Changzhu Xu、Jianguo Du、Lichao Ma、Guowei Li、Minli Tao、Wenqin Zhang

  DOI：10.1016/j.tet.2013.02.084

  日期：2013.6

  A tertiary amine immobilized fiber was prepared and used to efficiently catalyze tandem Michael-intramolecular Henry reactions between 1,4-dithiane-2,5-diol and trans-beta-nitrostyrenes to form the corresponding tetrahydrothiophene derivatives. This newly developed fiber catalyst is applicable to a wide range of trans-beta-nitroalkenes and affords good to excellent yields (75-93%) under mild conditions (with 2.5 mol % fiber catalyst at 50 C in ethanol for 5 h). The fiber catalyst exhibits excellent recyclability and reusability (up to 10 times) after simple workup procedure with only a slight loss in catalytic activity. It is noteworthy that the major diastereomers have r-R, trans-nitro, trans-hydroxy configurations with diastereoselectivities of up to 15:1. This differs from the results obtained when the same reaction is catalyzed by a homogeneous catalyst. This is the first example of a fiber catalyst exhibiting excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.