1-(2-烯丙基-3,6-二羟基苯基)乙烷-1-酮 | 40815-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-烯丙基-3,6-二羟基苯基)乙烷-1-酮
• 英文名称: 2-acetyl-3-allyl-1,4-benzenediol
• 英文别名: 2,5-dihydroxy-6-allylacetophenone；2-acetyl-3-prop-2'-enyl-1,4-hydroquinone；6'-allyl-2',5'-dihydroxyacetophenone；2,5-Dihydroxy-6-allylacetophenon；1-(2-Allyl-3,6-dihydroxy-phenyl)-aethanon；1-(2-allyl-3,6-dihydroxyphenyl)ethanone；1-(2-Allyl-3,6-dihydroxyphenyl)ethan-1-one；1-(3,6-dihydroxy-2-prop-2-enylphenyl)ethanone
• CAS: 40815-79-0
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD00100489
• 分子量: 192.214
• InChiKey: SKTNLXOVRHCAQS-UHFFFAOYSA-N

物化性质

• 熔点：
  107°C5
• 沸点：
  369.1±42.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  1-(2-烯丙基-3,6-二羟基苯基)乙烷-1-酮 在 镍 三乙基硅烷 、 甲酸 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 100.5h， 生成 6-(3-乙酰基-4-羟基-2-丙基-苯氧基)-己酸
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 74.0h， 生成 1-(2-烯丙基-3,6-二羟基苯基)乙烷-1-酮
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018

文献信息

• Claisen rearrangement of meta-substituted allyl phenyl ethers
  作者：J. Malcolm Bruce、Yusuf Roshan-Ali

  DOI：10.1039/p19810002677

  日期：——

  Electron-releasing substituents at the 3-position of allyl phenyl ethers favour Claisen rearrangement of the allyl group to the 6-position, whereas electron-acceptors favour migration to the 2-position. 2-Acylhydroquinone 4-allyl ethers yield, predominantly, the 3-allyl isomers, probably because internal hydrogen bonding confers naphthalenoid character on the aryl residue.

  烯丙基苯基醚3位的电子释放取代基有利于烯丙基的Claisen重排至6位，而电子受体则有利于向2位迁移。2-酰基氢醌4-烯丙基醚主要产生3-烯丙基异构体，这可能是因为内部氢键使芳基残基具有萘类特征。
• Non-Catalyzed Thermal Reactions of Acylquinones with Allylstannanes
  作者：Kazuhiro Maruyama、Yoshihiro Matano

  DOI：10.1246/bcsj.62.3877

  日期：1989.12

  Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (1H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From 1H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

  酰基喹诺酮与烯丙基锡在苯中的热反应经过硅胶柱层析后产生了几种产品；包括酰基烯丙基喹诺酮、酰基烯丙基环氧喹诺酮、含锡基团的环戊烷类化合物、烯丙基羟基喹诺酮、酰基羟基喹诺酮和酰基烯丙基羟基喹诺酮。主要产品是环戊烷类化合物，它们是新型的 [2+3] 环加成物，具有三烷基锡基团的 1,2-迁移。通过光谱学检查（1H NMR 和 Vis-UV），我们确认了反应途径，四种前体最初通过极化紧配对生成，并在柱层析纯化过程中转化为孤立的产品。在乙腈中的类似反应显示出明显的反应性差异，即生成酰基烯丙基喹诺酮及其对应的羟基喹诺酮，但完全不产生 [2+3] 环加成物。从 1H NMR 检查中确认，三种类型的前体在初始阶段通过溶剂分离离子对生成。酰基喹诺酮对烯丙基锡的较强反应性将是由于酰基的电子吸引能力。
• Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans
  作者：Yoshinari Sawama、Keiichiro Nakajima、Takaaki Aijima、Miyu Mae、Shinsuke Komagawa、Hiroki Nakata、Hironao Sajiki、Shuji Akai

  DOI：10.1248/cpb.c24-00231

  日期：2024.6.19

  Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative

  二氢苯并呋喃是生物活性化合物和天然产物的重要骨架。对苯二酚可以很容易地修饰成取代的对苯二酚，其有效地进行氧化生成相应的苯醌衍生物。苯醌是反应性亲电子试剂，经常用于与烯烃偶联生成二氢苯并呋喃。在此，我们报道了在路易斯酸性FeCl 3和2,3-二氯-5,6-二氰基-p-存在下，C2位带有吸电子基团的对苯二酚与烯烃一锅氧化偶联生成二氢苯并呋喃。苯醌（DDQ）氧化剂。此外，该方法还应用于N-吸电子基团取代的4-氨基苯酚的氧化偶联。  全尺寸图像
• Lewis acid mediated allylation of 2-alkanoyl-1,4-quinones with allylsilane and allylstannane
  作者：Yoshinori Naruta、Hidemitsu Uno、Kazuhiro Maruyama

  DOI：10.1016/s0040-4039(01)92464-5

  日期：——
• Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin
  作者：Adushan Pillay、Amanda L. Rousseau、Manuel A. Fernandes、Charles B. de Koning

  DOI：10.1016/j.tet.2012.06.052

  日期：2012.9

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.