9-(2-hydroxy-6-oxocyclohex-1-enyl)-2,3,4,9-tetrahydroxanthen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(2-hydroxy-6-oxocyclohex-1-enyl)-2,3,4,9-tetrahydroxanthen-1-one
• 英文别名: 1H-Xanthen-1-one, 2,3,4,9-tetrahydro-9-(2-hydroxy-6-oxo-1-cyclohexenyl)-；9-(2-hydroxy-6-oxocyclohexen-1-yl)-2,3,4,9-tetrahydroxanthen-1-one
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: IEJXFBPSOACJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 水杨醛 在 citrus limonium extract 作用下， 以 水 为溶剂， 反应 1.0h， 以87%的产率得到9-(2-hydroxy-6-oxocyclohex-1-enyl)-2,3,4,9-tetrahydroxanthen-1-one
  参考文献：
  名称：

  Bronsted acid-type biosurfactant for heterocyclization: a green protocol for benzopyran synthesis

  摘要：

  使用柠檬提取物作为绿色生物表面活性剂，从各种水杨醛和环状1,3-二酮合成苯并吡喃。

  DOI：

  10.1039/c5ra13652k

文献信息

• Glycerol as a promoting medium for electrophilic activation of aldehydes: catalyst-free synthesis of di(indolyl)methanes, xanthene-1,8(2H)-diones and 1-oxo-hexahydroxanthenes
  作者：Fei He、Peng Li、Yanlong Gu、Guangxing Li

  DOI：10.1039/b916015a

  日期：——

  Glycerol was used, for the first time, as a green and effective promoting medium for electrophilic activation of aldehydes, and with which, a catalyst-free system for some reactions that conventionally carried out using acid catalysts, such as synthesis of di(indolyl)methanes, 3,4,5,6,7,9-hexahydro-9-aryl-1H-xanthene-1,8(2H)-dione and 1-oxo-hexahydroxanthenes, was developed.

  甘油首次被用作绿色有效的促进介质，用于醛的电亲和活化，并基于此开发了一种无催化剂的体系，用于一些传统上使用酸催化剂进行的反应，例如二(吲哚基)甲烷、3,4,5,6,7,9-六氢-9-芳基-1H-黄酮-1,8(2H)-二酮和1-氧基-六氢黄酮的合成。
• l-Proline-accelerated, eco-friendly synthesis of 9-substituted-2,3,4,9-tetrahydro-1H-xanthen-1-ones under mild conditions
  作者：Davinder Prasad、Amreeta Preetam、Mahendra Nath

  DOI：10.1016/j.crci.2013.05.011

  日期：2013.12

  Résumé An efficient l-proline-accelerated synthesis of 9-substituted-2,3,4,9-tetrahydro-1H-xanthen-1-one derivatives has been accomplished via one-pot condensation of dimedone or 1,3-cyclohexanedione with substituted salicylaldehydes under mild reaction conditions. This protocol demonstrates several notable advantages, including operational simplicity, short reaction times, environmentally friendly conditions, no necessity of extraction and chromatographic purification steps, and high yields of the target products. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  摘要 通过将二酮或1,3-环己烷二酮与取代的水杨 aldehyde 在温和反应条件下进行一锅缩合，实现了高效的 l-脯氨酸加速合成 9-取代-2,3,4,9-四氢-1H-香豆素-1-酮衍生物。该方案显示出若干显著优势，包括操作简单、反应时间短、环保条件、不需要提取和色谱纯化步骤以及高产率的目标产品。 补充材料： 本文章的补充材料作为单独文件提供：mmc1.doc
• Nano Fe/NaY zeolite: an efficient and reusable solid-supported catalyst for synthesis of 1-oxo-hexahydroxanthene and tetraketone derivatives
  作者：Mahmood Tajbakhsh、Marzieh Heidary、Rahman Hosseinzadeh

  DOI：10.1007/s11164-015-2094-2

  日期：2016.2

  iron oxide (up to 32.8 %) with average diameter of 30–40 nm on the surface of NaY zeolite. The catalytic activity of nano Fe/NaY zeolite was examined in the preparation of 1-oxo-hexahydroxanthene and tetraketone derivatives. The results showed its applicability as a green, reusable, and promising catalyst for organic synthesis. This protocol demonstrates several notable advantages including short reaction

  摘要 通过离子交换技术在室温下成功合成了高铁离子含量的纳米Fe / NaY沸石。制备的Fe / NaY的特征在于X射线衍射，扫描电子显微镜，能量色散X射线光谱，Brunauer-Emmett-Teller（BET）表面积测量和傅立叶变换红外（FT-IR）光谱。数据分析证实，NaY沸石表面上存在平均直径为30–40 nm的氧化铁（高达32.8％）。在制备1-氧代六氢氧杂蒽和四酮衍生物时，研究了纳米Fe / NaY沸石的催化活性。结果表明其可作为绿色，可重复使用且有前途的有机合成催化剂。该协议展示了几个显着的优势，包括反应时间短，环境友好的条件，无需萃取或色谱纯化步骤，更方便的后处理，高收率的产品以及无需使用任何有害溶剂。回收催化剂并连续使用多达四次，而催化活性没有明显损失。 图形概要
• Bronsted acid-type biosurfactant for heterocyclization: a green protocol for benzopyran synthesis
  作者：Smita T. Morbale、Swati D. Jadhav、Madhukar B. Deshmukh、Suresh S. Patil

  DOI：10.1039/c5ra13652k

  日期：——

  Synthesis of benzopyran from the various salicylaldehydes and cyclic 1,3-diketones using catalytic amount of lemon extract as a green biosurfactant.

  使用柠檬提取物作为绿色生物表面活性剂，从各种水杨醛和环状1,3-二酮合成苯并吡喃。
• Catalytic Performance of Heteropolyacids as Efficient and Eco-Friendly Catalysts for the One-Pot Synthesis of Benzopyran Derivatives
  作者：Masoumeh Zakeri、Majid M. Heravi、Hossein A. Oskooie、Fatemeh F. Bamoharram

  DOI：10.1080/15533174.2010.522659

  日期：2010.11.30

  An efficient and improved procedure for the synthesis of benzopyran derivatives has been achieved with Keggin-type and Preyssler-type heteropolyacids (HPA) catalysts in one-pot reaction under solvent-free conditions.

  使用Keggin型和Preyssler型杂多酸（HPA）催化剂，在无溶剂条件下的一锅反应中，已经获得了一种高效且改进的合成苯并吡喃衍生物的方法。