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2-[3'-(4"-methylphenyl)prop-2'-ynyl]benzaldehyde | 267668-93-9

中文名称
——
中文别名
——
英文名称
2-[3'-(4"-methylphenyl)prop-2'-ynyl]benzaldehyde
英文别名
2-(3-(p-tolyl)prop-2-yn-1-yl)benzaldehyde;2-[3-(4-Methylphenyl)prop-2-ynyl]benzaldehyde
2-[3'-(4"-methylphenyl)prop-2'-ynyl]benzaldehyde化学式
CAS
267668-93-9
化学式
C17H14O
mdl
——
分子量
234.298
InChiKey
QWDDHDCJANOXGI-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    393.7±35.0 °C(Predicted)
  • 密度:
    1.10±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    4.1
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.12
  • 拓扑面积:
    17.1
  • 氢给体数:
    0
  • 氢受体数:
    1

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-[3'-(4"-methylphenyl)prop-2'-ynyl]benzaldehydebis(1,5-cyclooctadiene)nickel (0)三异丙基膦 作用下, 以 甲苯 为溶剂, 以70%的产率得到(E)-2-(4-methylbenzylidene)-2,3-dihydro-1H-inden-1-one
    参考文献:
    名称:
    Synthesis of 2,3-dihydro-1H-inden-1-one derivatives via Ni-catalyzed intramolecular hydroacylation
    摘要:
    An efficient synthetic method for the formation of 2,3-dihydro-1H-inden-1-one derivatives through a Ni-catalyzed intramolecular hydroacylation of 2-(prop-2-ynyl)benzaldehydes has been developed. Examination of various nickel and other transition metal catalysts and phosphine ligands showed that the use of Ni(COD)(2) catalyst combined with P(i-Pr)(3) ligand was the best choice to the success of the present intramolecular hydroacylation. A wide range of functional groups were tolerated, affording the corresponding substituted alpha-lidene-2,3-dihydro-1H-inden-1-ones in good to high yields with a sole E-selectivity under present reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tet.2012.03.053
  • 作为产物:
    描述:
    参考文献:
    名称:
    Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes
    摘要:
    开发了一种简单的方法用于合成不常见的2-丙炔基苯甲醛。研究表明,2-丙炔基苯甲醛是合成3-苄基异喹啉的合适构建块,通过在醋酸铵存在下进行微波促进的多米诺胺化/环异构化反应。最终在温和的反应条件下获得了一小批3-苄基异喹啉,并且产率良好。提出了两种可行的替代反应机理。
    DOI:
    10.1039/c4ob01583e
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文献信息

  • The Synthesis of Annulated Azepin-3-one Derivatives from 1,3,4-Pentatrienyl Nitrones by a Heterocyclization−Rearrangement Sequence
    作者:Karin Knobloch、Manfred Keller、Wolfgang Eberbach
    DOI:10.1002/1099-0690(200109)2001:17<3313::aid-ejoc3313>3.0.co;2-e
    日期:2001.9
    6 with potassium hydroxide or sodium methoxide in methanol at room temperature provides 1,2-dihydro[c]benzazepin-3-ones 9. The high product yields and the ease of the reactions under surprisingly mild conditions are particularly intriguing in view of the complex mechanistic pathway involved in the overall transformation. A mechanism based on a multistep rearrangement is proposed, involving conjugated
    在室温下在甲醇中用氢氧化钾或甲醇钠处理各种 6 型邻炔基芳基硝酮提供 1,2-二氢 [c] 苯并氮杂 9。在令人惊讶的温和条件下,产物产率高且反应容易考虑到整个转化过程中涉及的复杂机制途径,这些条件特别有趣。提出了一种基于多步重排的机制,涉及 13 型共轭丙二烯硝酮作为 1,7-偶极环化过程的前体,随后进行进一步的键重组,环丙酮 16 作为关键中间体。与丙二烯形成一致的是,使用三键异构体 12 和 37 可以实现相同的转化,它们包含末端烷基。异吲哚20作为次要产物的竞争形成支持环丙酮16的中间体。在用碱处理二氢萘并环化的硝酮 30 时,主要产物氮杂酮 31 的形成还伴随着异构异吲哚 32 的形成。一些选择性的 C=O 和 C=C 氢化反应,以及转化为硫酮 42和乙烯基溴 9p,已经用 9 的代表性例子进行了证明。
  • Dihydro[<i>c</i>]benzazepin-3-ones via Conjugated Nitrone−Allene Precursors
    作者:Karin Knobloch、Wolfgang Eberbach
    DOI:10.1021/ol0056832
    日期:2000.4.1
    [formula: see text] Treatment of o-propargylaryl nitrones with base provided 1,2-dihydro[c]benzazepin-3-ones in good yields. The straightforward transformation is explained on the basis of a multistep rearrangement involving conjugated allene-nitrones as precursors of a 1,7-dipolar electrocyclization process that is followed by further bond reorganizations.
    [式:见正文]用碱处理邻-炔丙基芳基硝酮可提供高产率的1,2-二氢[c]苯并ze庚因-3-酮。基于包括共轭亚丙基-硝酮作为1,7-偶极电环化过程的前体的多步重排,然后进行进一步的键重组,来解释直接转化。
  • 1,3-Dipolar Cycloaddition of Alkyne-Tethered <i>N</i>-Tosylhydrazones: Synthesis of Fused Polycyclic Pyrazoles
    作者:Yang Zheng、Xiaolu Zhang、Ruwei Yao、YueCheng Wen、Jingjing Huang、Xinfang Xu
    DOI:10.1021/acs.joc.6b02076
    日期:2016.11.18
    fused polycyclic pyrazoles via an intramolecular 1,3-dipolar cycloaddition reaction of alkyne-tethered tosylhydrazones has been reported. The pure solid products could be obtained without column chromatography in high to excellent yields, and the obtained products are useful bioactive molecules or could be used as the key intermediate for synthesis of these compounds in one or two steps. Additionally
    据报道,一般通过炔烃系甲苯磺酰hydr的分子内1,3-偶极环加成反应可以无过渡金属地进入稠合多环吡唑。无需柱色谱就可以高纯度到高产率获得纯固体产物,并且所得产物是有用的生物活性分子,或者可以用作一两个步骤合成这些化合物的关键中间体。此外,提出了[3 + 2]-环加成反应,然后进行直接H转移芳构化反应的机理,这与先前报道的芳基或烷基顺序的[1,5]-σ重排途径不同。
  • Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes
    作者:Monica Dell'Acqua、Valentina Pirovano、Giorgio Confalonieri、Antonio Arcadi、Elisabetta Rossi、Giorgio Abbiati
    DOI:10.1039/c4ob01583e
    日期:——
    An easy entry to uncommon 2-propargylbenzaldehydes was developed. 2-Propargylbenzaldehydes demonstrated to be suitable building blocks for the synthesis of 3-benzyl isoquinolines by microwave promoted domino imination/cycloisomerisation in the presence of ammonium acetate. A small library of 3-benzyl isoquinolines was obtained in good yields under mild reaction conditions. Two alternative plausible reaction mechanisms are proposed.
    开发了一种简单的方法用于合成不常见的2-丙炔基苯甲醛。研究表明,2-丙炔基苯甲醛是合成3-苄基异喹啉的合适构建块,通过在醋酸铵存在下进行微波促进的多米诺胺化/环异构化反应。最终在温和的反应条件下获得了一小批3-苄基异喹啉,并且产率良好。提出了两种可行的替代反应机理。
  • Synthesis of 2,3-dihydro-1H-inden-1-one derivatives via Ni-catalyzed intramolecular hydroacylation
    作者:Fan Yang、Tienan Jin、Yoshinori Yamamoto
    DOI:10.1016/j.tet.2012.03.053
    日期:2012.7
    An efficient synthetic method for the formation of 2,3-dihydro-1H-inden-1-one derivatives through a Ni-catalyzed intramolecular hydroacylation of 2-(prop-2-ynyl)benzaldehydes has been developed. Examination of various nickel and other transition metal catalysts and phosphine ligands showed that the use of Ni(COD)(2) catalyst combined with P(i-Pr)(3) ligand was the best choice to the success of the present intramolecular hydroacylation. A wide range of functional groups were tolerated, affording the corresponding substituted alpha-lidene-2,3-dihydro-1H-inden-1-ones in good to high yields with a sole E-selectivity under present reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
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