2-[hydroxy(3-trifluoromethylphenyl)methyl]cyclohex-2-enone | 743458-72-2

• 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: 2-[hydroxy(3-trifluoromethylphenyl)methyl]cyclohex-2-enone
• 英文别名: 2-[(R)-hydroxy-[3-(trifluoromethyl)phenyl]methyl]cyclohex-2-en-1-one
• CAS: 743458-72-2
• 化学式: C₁₄H₁₃F₃O₂
• 分子量: 270.251
• InChiKey: NXJUPSXPLHIKFZ-CYBMUJFWSA-N

物化性质

• 沸点：
  372.3±42.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 3-三氟甲基苯甲醛 在 三乙烯二胺 、 (R)-1,1'-(3,3'-bis(3,5-bis(trifluoromethyl)phenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diyl)-bis(3-(3,5-bis-trifluoromethyl)phenyl)thiourea 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 2-[羟基(3-三氟甲基苯基)甲基]环己-2-烯酮 、 2-[hydroxy(3-trifluoromethylphenyl)methyl]cyclohex-2-enone
  参考文献：
  名称：

  Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes with 2-Cyclohexen-1-one Catalyzed by Chiral Bis(Thio)urea and DABCO

  摘要：

  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.

  DOI：

  10.1021/ol7028806

文献信息

• 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。
• 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.