(2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol | 1574615-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: (2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol
• 英文别名: (2R,3R,4R)-3-nitro-2-thiophen-2-yl-3,4-dihydro-2H-thiochromen-4-ol
• CAS: 1574615-57-8
• 化学式: C₁₃H₁₁NO₃S₂
• 分子量: 293.367
• InChiKey: BWBHJQGRTBNIQM-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol 在 盐酸 、 zinc 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以87%的产率得到
  参考文献：
  名称：

  Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline–Aminophenol–Nickel-Catalyzed Michael/Henry Reaction

  摘要：

  The (S,S)-diphenylethylenediamine-derived imidazoline-aminophenol-Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with beta-nitrostyrenes to give the corresponding (2S,3R,4R)-2-aryl-3-nitrothiochroman-4-ols in up to 99% diastereoselectivity with 95% ee was demonstrated in diversity-oriented asymmetric catalysis. Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectiyity.

  DOI：

  10.1021/ol500361w
• 作为产物：
  描述：

  反式-2-(2-硝基乙烯基)噻吩 、 2-硫代水杨醛 在 2,4-二溴-6-[[[[(4S,5S)-4,5-二氢-4,5-二苯基-1-甲苯磺酰基-1H-咪唑-2-基]甲基][(S)-1-苯乙基]氨基]甲基]苯酚 、 nickel(II) acetate tetrahydrate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以99%的产率得到(2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol
  参考文献：
  名称：

  Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline–Aminophenol–Nickel-Catalyzed Michael/Henry Reaction

  摘要：

  The (S,S)-diphenylethylenediamine-derived imidazoline-aminophenol-Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with beta-nitrostyrenes to give the corresponding (2S,3R,4R)-2-aryl-3-nitrothiochroman-4-ols in up to 99% diastereoselectivity with 95% ee was demonstrated in diversity-oriented asymmetric catalysis. Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectiyity.

  DOI：

  10.1021/ol500361w

文献信息

• Chiral Bis(imidazolidine)iodobenzene (I-Bidine) Organocatalyst for Thiochromane Synthesis Using an Asymmetric Michael/Henry Reaction
  作者：Takayoshi Arai、Takumi Suzuki、Takahiro Inoue、Satoru Kuwano

  DOI：10.1055/s-0036-1588614

  日期：——

  Bis(imidazolidine)iodobenzene (I-Bidine) was designed as an organocatalyst based on previously reported imidazolidine- or oxazolidine-containing chiral metal catalysts. I-Bidine showed catalytic activity for the Michael/Henry reaction of thiosalicyl aldehydes with nitroalkenes to give optically active thiochromanes with moderate enantiomeric excesses.

  双（咪唑烷）碘苯（I-Bidine）被设计为基于先前报道的含有咪唑烷或恶唑烷的手性金属催化剂的有机催化剂。I-Bidine 对硫代水杨醛与硝基烯烃的 Michael/Henry 反应显示出催化活性，以得到具有适度对映体过量的光学活性硫色满。
• Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline–Aminophenol–Nickel-Catalyzed Michael/Henry Reaction
  作者：Takayoshi Arai、Yushi Yamamoto

  DOI：10.1021/ol500361w

  日期：2014.3.21

  The (S,S)-diphenylethylenediamine-derived imidazoline-aminophenol-Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with beta-nitrostyrenes to give the corresponding (2S,3R,4R)-2-aryl-3-nitrothiochroman-4-ols in up to 99% diastereoselectivity with 95% ee was demonstrated in diversity-oriented asymmetric catalysis. Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectiyity.