(R)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione | 1308657-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
• 英文别名: (R)-2-[1-(2-bromophenyl)-2-nitroethyl]-3-hydroxy-1,4-naphthoquinone
• CAS: 1308657-28-4
• 化学式: C₁₈H₁₂BrNO₅
• 分子量: 402.201
• InChiKey: DUJZHHUNBWMHDU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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 、 o-bromonitrostyrene 在 C₃₇H₃₁F₆N₃S 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 以95%的产率得到(R)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  联萘衍生的有机催化剂催化 2-羟基-1,4-萘醌与硝基烯烃的对映选择性迈克尔加成。

  摘要：

  描述了由联萘改性的手性双功能有机催化剂促进的 2-羟基-1,4-萘醌与硝基烯烃的高度对映选择性迈克尔加成。该反应在低催化剂负载（1 mol %）下以高产率（81-95%）和优异的对映选择性（91-98% ee）得到手性官能化萘醌。

  DOI：

  10.3762/bjoc.8.78

文献信息

• Chiral (thio)phosphorodiamides as excellent hydrogen bond donor catalysts in the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins
  作者：Ronghua Wu、Xufang Chang、Aidang Lu、Youming Wang、Guiping Wu、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1039/c1cc10797f

  日期：——

  A novel type of bidentate hydrogen bond donor catalysts based on (thio)phosphorodiamides catalophore has been developed for the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquione to nitroolefins, affording the corresponding adducts in high yields with excellent level of enantioselectivities (97- >99% ee).

  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）。
• 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.