4-nitro-5-phenyltetrahydrothiophen-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: 4-nitro-5-phenyltetrahydrothiophen-3-ol
• 英文别名: (3R,4R,5S)-4-nitro-5-phenylthiolan-3-ol
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: ZDAFJHSIOWBZAZ-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  苯甲醛 在 ammonium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 4-nitro-5-phenyltetrahydrothiophen-3-ol 、 4-nitro-5-phenyltetrahydrothiophen-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

• Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
  作者：Sara Meninno、Chiara Volpe、Giorgio Della Sala、Amedeo Capobianco、Alessandra Lattanzi

  DOI：10.3762/bjoc.12.63

  日期：——

  An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities.

  一项关于立体选择性串联磺酰-迈克尔/醛缩反应的研究结果被提出，该反应以硝基烯烃和市售的1,4-二硫代醚-2,5-二醇为底物，生成带有季碳立体中心的3,4,5-取代四氢噻吩。当使用反式-β-甲基-β-硝基苯乙烯时，由(R,R)-1,2-二苯乙胺衍生的二级胺硫脲被发现是最有效的催化剂，产物收率良好，立体选择性适中。
• Facile Synthesis of 3-Nitro-2-substituted Thiophenes
  作者：Cornelius J. O’ Connor、Mark D. Roydhouse、Anna M. Przybył、Michael D. Wall、J. Mike Southern

  DOI：10.1021/jo902656y

  日期：2010.4.16

  A new approach to 3-nitro-2-substituted thiophenes has been developed. Exposure of commercially available 1,4-dithane-2,5-diol to nitroalkenes in the presence of 20% triethylamine results in a tandem Michael intramolecular Henry reaction to form the corresponding tetrahydrothiophene. Subsequent microwave irradiation on acidic alumina in the presence of chloranil effects the solvent free dehydration and aromatization to form 3-nitro-2-substituted thiophenes cleanly and rapidly. A simple workup procedure removes the requirement for purification by chromatography in most cases.
• 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.