2-[(4-溴苯基)羟甲基]环己-2-烯酮 | 1013935-76-6

• 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-[(4-溴苯基)羟甲基]环己-2-烯酮
• 英文名称: 2-[(4-bromophenyl)hydroxymethyl]cyclohex-2-enone
• 英文别名: 2-[(S)-(4-bromophenyl)-hydroxymethyl]cyclohex-2-en-1-one
• CAS: 1013935-76-6
• 化学式: C₁₃H₁₃BrO₂
• 分子量: 281.149
• InChiKey: HXXXHTGEEIZYSW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-环己烯-1-酮 、 对溴苯甲醛 在 enzyme BH_32.14 作用下， 以 aq. phosphate buffer 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  为 Morita-Baylis-Hillman 反应设计一种高效的对映选择性酶

  摘要：

  计算设计和定向进化的结合可以提供一种通用策略来创建具有新功能的酶。到目前为止，这种方法已经为少数模型反应提供了酶。在这里，我们表明可以将新的催化机制设计到蛋白质中以加速更具挑战性的化学转化。原始设计的进化优化为 Morita-Baylis-Hillman (MBH) 反应提供了一种高效的对映选择性酶 (BH32.14)。BH32.14 适用于制备规模的转化，接受范围广泛的醛和烯酮偶联伙伴，并能够促进二醛的选择性单官能化。晶体学、生物化学和计算研究表明 BH32。14 通过复杂的催化机制运作，该机制包括 His23 亲核试剂与明智定位的 Arg124 配对。这种催化精氨酸在构象状态之间穿梭以稳定多个氧阴离子中间体，并作为特殊双齿氢键催化剂（例如，硫脲）的遗传编码替代物。这项研究表明，可以从头开始构建精心设计的催化装置，以促进在自然界中未观察到的要求苛刻的多步过程。

  DOI：

  10.1038/s41557-021-00833-9

文献信息

• 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.
• Asymmetric Morita–Baylis–Hillman reaction catalyzed by pepsin
  作者：Jing-Wen Xue、Jian Song、Ian C.K. Manion、Yan-Hong He、Zhi Guan

  DOI：10.1016/j.molcatb.2015.12.002

  日期：2016.2

  Pepsin from porcine gastric mucous shown catalytic promiscuity was first discovered to catalyze the Morita-Baylis-Hillman (MBH) reaction between aromatic aldehydes with 2-cyclohexen-1-one or 2-cyclopenten-i-one in a two-phase medium of phosphate buffer/cyclohexane in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). The best results of the corresponding MBH products up to 77% yield and 38% ee were achieved. (C) 2015 Elsevier B.V. All rights reserved.