(S)-2-hydroxy-3-(2-nitro-1-(thiophen-2-yl)ethyl)naphthalene-1,4-dione | 1037774-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-hydroxy-3-(2-nitro-1-(thiophen-2-yl)ethyl)naphthalene-1,4-dione
• CAS: 1037774-82-5
• 化学式: C₁₆H₁₁NO₅S
• 分子量: 329.333
• InChiKey: NHASPGINTUNDNF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.51
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-硝基乙烯基噻吩 、 2-羟基-1,4-萘醌 在 (1R,2R)-1-N-[[[(1R,2R)-2-(dimethylamino)cyclohexyl]amino]-phenylphosphinothioyl]-2-N,2-N-dimethylcyclohexane-1,2-diamine 作用下， 以 乙腈 为溶剂， 反应 66.0h， 以77%的产率得到(S)-2-hydroxy-3-(2-nitro-1-(thiophen-2-yl)ethyl)naphthalene-1,4-dione
  参考文献：
  名称：

  手性（硫代）磷二酰胺是出色的氢键供体催化剂，用于将2-羟基-1,4-萘醌酮不对称迈克尔加成到硝基烯烃中。

  摘要：

  已经开发出了一种新型的基于（硫代）磷二酰胺基阴极的双齿氢键供体催化剂，用于将2-羟基-1,4-萘并醌不对称地迈克尔加成到硝基烯烃中，从而以高收率提供相应的加合物，同时具有出色的对映选择性（ 97-> 99％ee）。

  DOI：

  10.1039/c1cc10797f

文献信息

• Sugar thiourea catalyzed highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to β-nitroalkenes
  作者：B. V. Subba Reddy、S. Madhusudana Reddy、Manisha Swain

  DOI：10.1039/c2ra22270a

  日期：——

  A highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to β-nitrostyrenes has been achieved using a novel class of sugar-Cinchona thiourea conjugates. The method offers significant advantages such as low catalyst loading (1 mol%), high enantioselectivity (up to 99% ee), short reaction times and ambient reaction conditions.

  利用一类新型糖-金鸡纳硫脲偶联物，实现了2-羟基-1,4-萘醌对β-硝基苯乙烯的高度对映选择性迈克尔加成反应。该方法具有显著优势，如催化剂用量低（1摩尔%）、高对映选择性（可达99% 对映体过量）、反应时间短和环境反应条件。
• Continuous Flow, Highly Enantioselective Michael Additions Catalyzed by a PS-Supported Squaramide
  作者：Pinar Kasaplar、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1021/ol400974z

  日期：2013.7.19

  A polystyrene (PS) supported bifunctional squaramide organocatalyst promotes fast Michael addition of 2-hydroxy-1,4-naphthoquinone to nitroalkenes with very high enantioselectivities at low catalyst loadings. The polystyrene supported catalyst can be recycled up to 10 times without any decrease in enantioselectivity (average 96% ee) and adapted to continuous flow operation (24 h). A single flow experiment involving six different nitroalkenes in a sequential manner highlights the applicability of this methodology for rapid access to chemical diversity.
• BINOL–quinine–squaramides as efficient organocatalysts for the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquinone to nitroalkenes
  作者：Enshan Zhou、Bin Liu、Chune Dong

  DOI：10.1016/j.tetasy.2013.11.019

  日期：2014.1

  A set of BINOL-quinine-squaramides were synthesized, and then used as organocatalysts to promote the catalytic enantioselective Michael addition reaction of 2-hydroxy-1,4-naphthoquinone to nitroalkenes with excellent yields and ees (up to 99% yield and 93% ee) at low catalyst loading (0.5 mol %). (C) 2013 Elsevier Ltd. All rights reserved.