2-(2-methoxyphenyl)cyclohex-2-enone | 137273-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-methoxyphenyl)cyclohex-2-enone
• 英文别名: 2-(2-Methoxyphenyl)cyclohex-2-en-1-one
• CAS: 137273-41-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: WHBQPAVZHFVJJR-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  366.6±42.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-methoxyphenyl)cyclohex-2-enone 在 重铬酸吡啶 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(2-Methoxyphenyl)-3-(1-trimethylsilylethenyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone

  摘要：

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

  DOI：

  10.1021/jo970570q
• 作为产物：
  描述：

  2-(2-methoxy-phenyl)-cyclohex-2-enol 在 aluminum tri-tert-butoxide 、 丙酮 作用下， 生成 2-(2-methoxyphenyl)cyclohex-2-enone
  参考文献：
  名称：

  109.吗啡系列的初步合成。第二部分 2-芳基环己-2-烯酮的合成

  摘要：

  DOI：

  10.1039/jr9510000516

文献信息

• Dynamic Kinetic Resolution of γ-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters
  作者：Dan Yang、Xiong Wu、Xiao-Jie Zheng、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.1c01689

  日期：2021.7.2

  An efficient asymmetric hydrogenation of racemic γ-substituted cyclic β-ketoesters via dynamic kinetic resolution to provide chiral cyclic β-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-5 (Ir-SpiroSAP), a series of racemic γ-aryl/alkyl substituted cyclic β-ketoesters were hydrogenated to the corresponding chiral cyclic β-hydroxy esters in

  据报道，外消旋 γ-取代的环状 β-酮酯通过动态动力学拆分有效不对称氢化，以提供具有三个连续立体中心的手性环状 β-羟基酯。使用手性螺铱催化剂 ( R ) -5 (Ir-SpiroSAP)，一系列外消旋 γ-芳基/烷基取代的环状 β-酮酯以高产率 (84-97%) 氢化成相应的手性环状 β-羟基酯) 具有良好到出色的对映选择性 (69–>99% ee)和顺式、顺式选择性（高达 >99:1）。
• Preparation of 3-oxo-2-cyclohexen-2-ylzinc iodides and their palladium-mediated reactions with aryl or alkenyl halides
  作者：R. Rossi、F. Bellina、D. Ciucci

  DOI：10.1016/s0022-328x(97)00294-5

  日期：1997.9

  of 98% pure zinc dust (< 10 micron), which must be activated with chlorotrimethylsilane. In the presence of a palladium(0) catalyst precursor, compounds 11 undergo cross-coupling reactions with aryl or alkenyl halides bearing a variety of functional groups to give in moderate to high yields the desired 2-substituted 2-cyclohexen-1-ones 12.

  2-Iodo-2-cyclohexen-1-ones 10在温和条件下与大量过量（4当量）的活化Zn（Ag）对在TMEDA（1当量）存在下反应，生成相应的3-oxo -2-环己烯-2-基碘化锌11的收率很高。这些新的有机锌试剂也可以通过使10与TMEDA（1当量）与大量过量（4当量）的98％纯锌粉（<10微米）反应而制备，必须用三甲基氯硅烷将其活化。在钯（0）催化剂前体的存在下，化合物11与带有各种官能团的芳基或烯基卤化物进行交叉偶联反应，以中等至高收率获得所需的2-取代的2-环己烯-1-酮12。
• Asymmetric Hydrogenation of Racemic 6-Aryl 1,4-Dioxaspiro[4.5]decan-7-ones to Functionalized Chiral β-Aryl Cyclohexanols via a Dynamic Kinetic Resolution
  作者：Dan Yang、Ai-Jiao Yang、Yong Chen、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.1c00044

  日期：2021.3.5

  asymmetric hydrogenation method for the synthesis of functionalized β-aryl cyclohexanols is described. With chiral spiro ruthenium catalyst (Ra,S,S)-5c, a series of racemic α-aryl cyclohexanones bearing a β-monoethylene ketal group were hydrogenated to the corresponding functionalized β-aryl cyclohexanols in high yields with enantioselectivity of up to 99% ee via a dynamic kinetic resolution. This protocol

  描述了用于合成官能化的β-芳基环己醇的钌催化的不对称氢化方法。用手性螺钌催化剂（R a，S，S）-5c将一系列带有β-单亚乙基缩酮的外消旋α-芳基环己酮氢化成相应的官能化β-芳基环己醇，对映选择性高达99通过动态动力学分辨率得到的ee百分比。该协议可以以十亿分之一规模进行，并为光学活性和高密度官能化的芳基环己醇的合成提供了可能的方法。
• Sequential Michael Addition/Electrophilic Alkynylation: Synthesis of α-Alkynyl-β-Substituted Ketones and Chromanones
  作者：Bruno V. M. Teodoro、Luiz F. Silva

  DOI：10.1021/acs.joc.8b02251

  日期：2018.11.2

  α-alkynyl-β-substituted cyclic ketones and analogue chromanones via one-pot Michael addition/hypervalent iodine-based α-alkynylation. Cu(I)-catalyzed Michael addition using either alkyl-aluminum or Grignard reagents, followed by diastereoselective electrophilic alkynylation of the resulting enolate by 1-ethynyl-1λ3,2-benziodoxol-3(1H)-one (EBX) resulted in the α-alkynyl-β-substituted cyclic ketones or chromanones

  我们描述了通过一锅迈克尔加成/基于碘的高价基于α-炔基的α-炔基-β-取代的环酮和类似的发色酮的合成。的Cu（I），使用任一烷基铝或格氏试剂催化的Michael加成，接着将得到的烯醇化物的非对映选择性亲电炔基由1-乙炔基1λ 3，2-苯碘酰-3（1H） -酮（EBX）导致α-炔基-β-取代的环酮或苯并二氢吡喃酮的收率在34-89％之间（16个实例）。该反应成功地扩大规模至5 mmol规模，并证明了模型炔基化酮的进一步功能化。
• The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts
  作者：Zilong Tang、Benoit Mathieu、Bernard Tinant、Georges Dive、Léon Ghosez

  DOI：10.1016/j.tet.2007.05.086

  日期：2007.8

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.