2-[(4-氟苯基)羟甲基]环己-2-烯酮 | 1013935-79-9

• 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-氟苯基)羟甲基]环己-2-烯酮
• 英文名称: 2-[(4-fluorophenyl)hydroxymethyl]cyclohex-2-enone
• 英文别名: 2-[(S)-(4-fluorophenyl)-hydroxymethyl]cyclohex-2-en-1-one
• CAS: 1013935-79-9
• 化学式: C₁₃H₁₃FO₂
• 分子量: 220.243
• InChiKey: MSRQKLMVJFOOMK-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  3

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 对氟苯甲醛 在 三乙烯二胺 、 pepsin from porcine gastric mucosa [P₇₁₂₅-100G, Lot No_.SLBD₇₆₉₈V, 130 units/mg solid] 作用下， 以 aq. phosphate buffer 、 环己烷 为溶剂， 反应 96.0h， 以16%的产率得到
  参考文献：
  名称：

  Asymmetric Morita–Baylis–Hillman reaction catalyzed by pepsin

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2015.12.002

文献信息

• Asymmetric Morita–Baylis–Hillman reactions of 2-cyclohexen-1-one catalyzed by chiral biaryl-based bis(thiourea) organocatalysts
  作者：Yuki Nakayama、Takashi Gotanda、Katsuji Ito

  DOI：10.1016/j.tetlet.2011.09.064

  日期：2011.11

  Newly-developed bis(thiourea) 1d was found to be an efficient organocatalyst for the Morita-Baylis-Hillman reaction. High enantioselectivities were obtained in the reaction of 2-cyclohexen-1-one with both aromatic aldehydes (up to 84% ee) and aliphatic aldehydes (up to 96% ee). (C) 2011 Elsevier Ltd. All rights reserved.
• Enantiopure trans-1-amino-2-(arylsulfanyl)cyclohexanes: novel chiral motifs for ligands and organocatalysts
  作者：Anna E. Nowak、Elżbieta Wojaczyńska、Jacek Skarżewski

  DOI：10.1016/j.tetasy.2011.09.015

  日期：2011.9

  In order to obtain the title compounds (1R,2R)-cyclohexane-1,2-diol was stereoselectively converted into cis-(1R,2S)-2-(arylsulfanyl)cyclohexanols and these products were submitted to the nucleophilic substitution via the Mitsunobu reaction (HN3, DEAD). Reduction of the isolated azides gave the desired trans-(1S,2S)-1-amino-2-(arylsulfanyl)cyclohexanes. The (1S,2S)-1-amino-2-(2-aminophenylsulfanyl)cyclohexanes thus prepared were reacted with 3,5-bis(trifluoromethyl)phenyl isothiocyanate to furnish the respective bis-thiourea compounds. An application of a derivative of this type as an organocatalyst (20 mol %) in the Baylis-Hillman reaction gave the respective product in up to 93% ee. (C) 2011 Elsevier Ltd. 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.