(R)-2-(hydroxy(phenyl)methyl)cyclopent-2-enone | 1328915-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(hydroxy(phenyl)methyl)cyclopent-2-enone
• 英文别名: 2-[(R)-hydroxy(phenyl)methyl]cyclopent-2-en-1-one
• CAS: 1328915-98-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: SRGXMVBNZHFVLJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 苯甲醛 在 4-二甲氨基吡啶 、 (-)-N-十二基-N-甲基麻黄碱溴化物 作用下， 以 水 为溶剂， 反应 17.0h， 以43.9%的产率得到
  参考文献：
  名称：

  Cationic chiral surfactant based micelle-guided asymmetric Morita-Baylis-Hillman reaction

  摘要：

  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.

  DOI：

  10.1016/j.catcom.2016.05.010

文献信息

• A highly efficient kinetic resolution of Morita–Baylis–Hillman adducts achieved by N–Ar axially chiral Pd-complexes catalyzed asymmetric allylation
  作者：Feijun Wang、Shengke Li、Mingliang Qu、Mei-Xin Zhao、Lian-Jun Liu、Min Shi

  DOI：10.1039/c1cc15543a

  日期：——

  Palladium complexes with an axially chiral N–Ar framework have been developed. These complexes showed high stereoselectivities in asymmetric allylic arylation to achieve the kinetic resolution of Morita–Baylis–Hillman adducts, affording up to 99% ee of (E)-allylation products and 92% ee of recovered Morita–Baylis–Hillman adducts.

  我们开发了具有轴向手性 NâAr 框架的钯配合物。这些配合物在不对称烯丙基芳基化过程中表现出很高的立体选择性，从而实现了莫里塔-贝利斯-希尔曼加合物的动力学解析，得到的(E)-烯丙基化产物的ee高达99%，回收的莫里塔-贝利斯-希尔曼加合物的ee高达92%。
• 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。
• 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.