2-[羟基-(4-硝基苯基)甲基]环戊-2-烯酮 | 1013935-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[羟基-(4-硝基苯基)甲基]环戊-2-烯酮
• 英文名称: 2-[hydroxy-(4-nitrophenyl)methyl]cyclopent-2-enone
• 英文别名: 2-[Hydroxy(4-nitrophenyl)methyl]-cyclopent-2-en-1-one；2-[(S)-hydroxy-(4-nitrophenyl)methyl]cyclopent-2-en-1-one
• CAS: 1013935-85-7
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: LQLZQMAPCAUIHT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 对硝基苯甲醛 在 (R)-(+)-4-dimethylaminopyrindinyl(pentaphenylcyclo-pentadienyl)iron 、 magnesium iodide 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 2-[hydroxy-(4-nitrophenyl)methyl]cyclopent-2-enone 、 2-[羟基-(4-硝基苯基)甲基]环戊-2-烯酮
  参考文献：
  名称：

  利用手性DMAP催化剂，MgI 2促进环戊烯酮的对映选择性森田-贝利斯-希尔曼反应。

  摘要：

  Fu的平面手性DMAP催化剂可在存在MgI（2）作为助催化剂的情况下，有效地促进环戊烯酮与多种醛类的不对称Morita-Baylis-Hillman反应。

  DOI：

  10.1039/c001977a

文献信息

• MgI2-accelerated enantioselective Morita–Baylis–Hillman reactions of cyclopentenone utilizing a chiral DMAP catalyst
  作者：Alejandro Bugarin、Brian T. Connell

  DOI：10.1039/c001977a

  日期：——

  Fu's planar chiral DMAP catalyst efficiently promotes the asymmetric Morita-Baylis-Hillman reactions of cyclopentenone with a variety of aldehydes in the presence of MgI(2) as a cocatalyst.

  Fu的平面手性DMAP催化剂可在存在MgI（2）作为助催化剂的情况下，有效地促进环戊烯酮与多种醛类的不对称Morita-Baylis-Hillman反应。
• Kinetic Resolution of Hindered Morita–Baylis–Hillman Adducts by Rh(I)-Catalyzed Asymmetric 1,4-Addition/β-Hydroxyelimination
  作者：Yazhou Wang、Xiangqing Feng、Haifeng Du

  DOI：10.1021/ol202069e

  日期：2011.9.16

  Morita–Baylis–Hillman adducts has been successfully achieved in excellent selectivities via Rh(I)-catalyzed asymmetric 1,4-addition/β-hydroxyelimination with the use of a chiral sulfinamide/olefin hybrid ligand. This study provides a novel and efficient access to both optically active hindered highly functionalized alkenes and Morita–Baylis–Hillman adducts.

  受阻的Morita-Baylis-Hillman加合物的动力学拆分已通过使用手性亚磺酰胺/烯烃杂化配体通过Rh（I）催化的不对称1,4-加成/β-羟基消除反应以优异的选择性成功实现。这项研究为光学活性受阻的高度官能化烯烃和Morita-Baylis-Hillman加合物提供了新颖而有效的途径。
• Comparison between Chemoenzymatic and Bienzymatic Cascades Leading to Morita–Baylis–Hillman Adducts
  作者：Yinuo Li、Cuiyu Bao、Zhoutong Sun、Wuyuan Zhang、Bo Yuan

  DOI：10.1002/cctc.202201621

  日期：——

  Chemoenzymatic and bienzymatic cascades: We herein present three cascade routes to produce MBH adducts and compare the key advantages and challenges of the chemoenzymatic and bienzymatic methodologies.

  化学酶促和双酶促级联：我们在此提出了三种级联途径来生产 MBH 加合物，并比较了化学酶促和双酶促方法的主要优势和挑战。
• Cationic chiral surfactant based micelle-guided asymmetric Morita-Baylis-Hillman reaction
  作者：Bashir Ahmad Shairgojray、Aijaz Ahmad Dar、Bilal A. Bhat

  DOI：10.1016/j.catcom.2016.05.010

  日期：2016.8

  Cationic chiral surfactant (1R, 2S)-(-)-N-dodecyl-N-methylephedrinium bromide (DMEB) was utilized for the first time in inducing asymmetry to Morita-Baylis-Hillman reaction in aqueous medium. Proton NMR studies carried out to determine the locus of the reaction in micro-heterogeneous micellar environment, were found useful in proposing a plausible model for asymmetric induction. This work demonstrates that under such mild and nonhazardous reactions conditions, the reaction rates increase, good yields are favored and above all reasonable enantiomeric excesses are obtained. (C) 2016 Elsevier B.V. All rights reserved.
• Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes with 2-Cyclohexen-1-one Catalyzed by Chiral Bis(Thio)urea and DABCO
  作者：Min Shi、Xu-Guang Liu

  DOI：10.1021/ol7028806

  日期：2008.3.1

  Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H-8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was achieved in the reaction of 3-fluorobenzaldehyde with 2-cyclohexen-1-one to give the desired Morita-Baylis-Hillman product in 79% yield and 88% ee.