(S)-2-(1-(4-chlorophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione | 1037774-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(1-(4-chlorophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
• CAS: 1037774-78-9
• 化学式: C₁₈H₁₂ClNO₅
• 分子量: 357.75
• InChiKey: WEANVKDPRHRGQL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  97.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 1-(4-氯苯基)-2-硝基乙烯 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 12.0h， 以85%的产率得到(S)-2-(1-(4-chlorophenyl)-2-nitroethyl)-3-hydroxynaphthalene-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。
• A Recyclable Hydrophobic Anchor-Tagged Asymmetric Amino Thiourea Catalyst
  作者：Takahisa Jichu、Tsubasa Inokuma、Keisuke Aihara、Taiki Kohiki、Kodai Nishida、Akira Shigenaga、Ken-ichi Yamada、Akira Otaka

  DOI：10.1002/cctc.201800714

  日期：2018.8.21

  A novel, recyclable, thiourea‐based asymmetric organocatalyst containing a hydrophobic anchor has been developed. The chemical nature of the hydrophobic anchor contributes to the desirable characteristics of the recyclable catalyst. The hydrophobic anchor‐tagged thiourea catalyst is highly soluble in less polar solvents, which is compatible with amino thiourea catalyst‐mediated asymmetric reaction

  已经开发了一种新型的，可回收的，基于硫脲的不对称有机催化剂，其中含有疏水性锚。疏水性锚的化学性质有助于可回收催化剂的所需特性。疏水性锚固标记的硫脲催化剂在极性较小的溶剂中高度可溶，与氨基硫脲催化剂介导的不对称反应条件相容，但在再循环过程中仅少量溶于极性溶剂。这种不对称催化剂提供的催化性能可与母体催化剂媲美，并且可以很容易地从反应中回收利用。
• 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.