1-(4-(2,2-diethoxyethoxy)-2-hydroxyphenyl)ethanone | 492440-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(2,2-diethoxyethoxy)-2-hydroxyphenyl)ethanone
• 英文别名: 1-(4-(2,2-diethoxyethoxy)-2-hydroxyphenyl)ethan-1-one；1-[4-(2,2-Diethoxy-ethoxy)-2-hydroxyphenyl]-ethanone；1-[4-(2,2-diethoxyethoxy)-2-hydroxyphenyl]ethanone
• CAS: 492440-03-6
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: SVMORPJKMUDVLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-(2,2-diethoxyethoxy)-2-hydroxyphenyl)ethanone 在 吡啶 、 amberlyst-15 、 硫酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 lanceolatin B
  参考文献：
  名称：

  Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones

  摘要：

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。

  DOI：

  10.1055/s-2004-831180
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 2-溴-1,1-二乙氧基乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到1-(4-(2,2-diethoxyethoxy)-2-hydroxyphenyl)ethanone
  参考文献：
  名称：

  Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones

  摘要：

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。

  DOI：

  10.1055/s-2004-831180

文献信息

• A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3·6H2O as a catalyst under solvent-free conditions
  作者：T. Srikanth Reddy、M. Narasimhulu、N. Suryakiran、K. Chinni Mahesh、K. Ashalatha、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.07.059

  日期：2006.9

  A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers

  在室温下，在无溶剂条件下，在催化量的La（NO 3）3 ·6H 2 O的存在下，通过用乙酸酐处理，可以将各种醇，酚和胺有效，选择性地转化为相应的乙酸酯。该方法与酸敏感的羟基保护基团（例如TBDMS，THP，OBz，OBn，Boc和一些异丙叉）兼容，并提供1,3-，1,4-和1,5-二醇单乙酸酯的优异收率。
• Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones
  作者：Atul Goel、Manish Dixit

  DOI：10.1055/s-2004-831180

  日期：——

  A novel approach to the total synthesis of naturally occurring furanoflavones and furanochalcones is described. Angular and linear furanoflavones and furanochalcones have been prepared in just four steps, using economical reagents and simple reaction conditions. The key step of our approach is the formation of crucial precursors, 5-acetyl-4-hydroxy-coumarone and 5-acetyl-6-hydroxy-coumarone by Amberlyst 15-catalyzed cyclization of phen­oxyacetal.

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。
• A Controlled Synthesis of Nature-Mimicking Benzofurans and their Corresponding Dimers
  作者：Atul Goel、Manish Dixit、Ashoke Sharon、Prakas Maulik

  DOI：10.1055/s-2006-944194

  日期：2006.6

  Benzofurans functionalized with hydroxy and acetyl functionalities are not only the core structures found in a large number of biologically important natural products, but also the vital precursors for several naturally occurring furanoflavonoids. Numerous synthetic methodologies are available in the literature for the ­synthesis of functionalized benzofurans but access to benzofurans with adjacent hydroxy and acetyl functionalities shows paucity of references. In this paper we report highly convenient synthesis of nature-mimicking benzofurans and their dimers from easily accessible precursors.

  羟基和乙酰基官能化的苯并呋喃不仅是大量生物活性天然产物中的核心结构，也是多种天然存在的呋喃黄酮类化合物的重要前体。文献中提供了许多合成官能化苯并呋喃的方法，但关于邻位羟基和乙酰基官能化苯并呋喃的文献却很少。本文中，我们报道了从易得的前体出发，高度便捷地合成仿生苯并呋喃及其二聚体的方法。
• Total synthesis of naturally occurring moracinflavan E and related compounds
  作者：Ting-Yu Lin、Chieh-Yu Chou、Yu-Hsuan Chen、Chien-Kuo Ku、Ming-Jaw Don

  DOI：10.1016/j.phytol.2022.05.011

  日期：2022.8

  A total synthesis of four flavans with a furan ring in different positions (1–4) was achieved successfully. The flavan was synthesized from flavanone by reduction and followed by deoxygenation steps. The synthesized compound 2 was confirmed as the naturally occurring moracinflavan E based on the comparison of their NMR spectral data.

  成功实现了在不同位置（1-4）具有呋喃环的四种黄烷的全合成。黄烷是由黄烷酮通过还原合成的，然后是脱氧步骤。合成的化合物2基于其 NMR 光谱数据的比较被确认为天然存在的 moracinflavan E。
• Novel synthesis of rotenoid, pongarotene, by oxidative rearrangement using thallium(III) <i>p</i>-tosylate
  作者：Chidvilas Kurapati、Om V. Singh、Rambabu Gundla

  DOI：10.1080/00397911.2022.2079990

  日期：2022.4.18

  Abstract The synthesis of furano-rotenoid, pongarotene, by oxidative 1,2-aryl rearrangement of the sprirochromanone (11) using thallium(III) p-tosylate as key step has been described. Pongarotene (12) structure was confirmed by 2D NMR, HRMS and finally by X-ray crystallography. The sprirochromanones were synthesized by radical cyclization of chromone derivative (10). This methodology will be useful

  摘要 已经描述了使用对甲苯磺酸铊 (III) 为关键步骤，通过sprirochromanone ( 11 ) 的氧化 1,2-芳基重排合成呋喃类鱼素、pongarotene。Pongarotene ( 12 ) 结构通过 2D NMR、HRMS 和最后通过 X 射线晶体学证实。螺色酮通过色酮衍生物 ( 10 )的自由基环化合成。这种方法可用于合成天然存在的类胡萝卜素。