pyrano<3,2-c>coumarin | 88538-37-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: pyrano<3,2-c>coumarin
• 英文别名: 2,2-dimethyl-pyrano[3,2-c][1]benzopyran-5-one；5-Oxo-5H-2,2-dimethylpyrano<3,2-c>benzopyran；2,2-dimethyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one；2,2-dimethyl-5H-pyrano(3,2-c)-1-benzopyrano-5-one；2,2-dimethyl-2H,5H-pyrano[3,2-c]chromen-5-one；2,2-dimethyl-2H-pyrano[3,2-c]chromen-5-one；2H,5H-Pyrano[3,2-c][1]benzopyran-5-one, 2,2-dimethyl-；2,2-dimethylpyrano[3,2-c]chromen-5-one
• CAS: 88538-37-8
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: VCPDXVSEZITDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pyrano<3,2-c>coumarin 在 二甲基二环氧乙烷 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以90%的产率得到(3R,4S)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

  摘要：

  An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-0-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.022
• 作为产物：
  描述：

  4-羟基香豆素 在 2,4-二硝基苯磺酸二水合物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 pyrano<3,2-c>coumarin
  参考文献：
  名称：

  异戊二烯经酸催化的4-羟基香豆素的区域发散环化：进入吡喃香豆素和吡喃色酮

  摘要：

  开发了一种酸催化的生物质衍生的4-羟基香豆素与异戊二烯的区域发散环化反应，可轻松获得吡喃香豆素和吡喃色酮。

  DOI：

  10.1002/ejoc.201901154

文献信息

• Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products
  作者：Ene Jin Jung、Byung Ho Park、Yong Rok Lee

  DOI：10.1039/c0gc00265h

  日期：——

  In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products.

  在水相介质中，通过多种环状1,3-二羰基化合物与若干α,β-不饱和醛的反应，以良好产率实现了吡喃的环保、简便、高效合成。关键策略是形式上的[3+3]环加成，通过多米诺Knoevenagel缩合/6π电环化反应实现。这一方法被应用于生物活性吡喃香豆素、吡喃喹啉酮和吡喃萘醌衍生物的合成，以及部分天然与合成产物的制备。
• Green One-Pot Synthesis of 2H-Pyrans Under Solvent-Free Conditions Catalyzed by Ethylenediammonium Diacetate
  作者：Martín J. Riveira、Mirta P. Mischne

  DOI：10.1080/00397911.2011.594975

  日期：2013.1

  Abstract Ethylenediammonium diacetate readily catalyzes the Knoevenagel-type condensation between 1,3-dicarbonyl substrates and α,β-unsaturated aldehydes at room temperature under solvent-free conditions. This rapid, efficient, and convenient one-pot approach to the synthesis of 2H-pyrans stands as a significant advance over previously reported protocols. This environmentally friendly methodology has

  摘要 二乙酸乙二铵在室温、无溶剂条件下很容易催化 1,3-二羰基底物与 α,β-不饱和醛之间的 Knoevenagel 型缩合反应。这种快速、高效、方便的一锅法合成 2H-吡喃是比之前报道的协议的重大进步。这种环境友好的方法已成功应用于合成生物活性天然产物 zanthosimuline、N-methylflindersine 和 ferprenin。补充材料可用于本文。访问出版商的 Synthetic Communications ® 在线版以查看免费的补充文件。图形概要
• Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2<i>H</i>-Chromenones, Pyranones, and Tetrahydroquinolinones
  作者：Julie Moreau、Claudie Hubert、Jessika Batany、Loic Toupet、Thierry Roisnel、Jean-Pierre Hurvois、Jean-Luc Renaud

  DOI：10.1021/jo901238y

  日期：2009.12.4

  Brønsted acids catalyze the addition of enolizable β-diketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.

  布朗斯台德酸通过形式化的[3 + 3]在温和的反应条件下催化将可烯化的β-二酮，β-酮酸酯和乙烯基酰胺添加到α，β-不饱和醛中，从而以高收率生成取代的色农酮，吡喃酮和四氢喹啉酮。环加成。
• Microwave-Assisted Solvent and Catalyst Free Synthesis of 2H-Pyrans
  作者：Naushad Edayadulla、Yong Rok Lee

  DOI：10.5012/bkcs.2013.34.10.2963

  日期：2013.10.20

  This paper describes a simple and efficient method involving domino Knovenegal/$6\pi}$ electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.

  本文描述了一种简单高效的方法，利用多米诺克诺维纳格尔/$6\pi}$电环化反应，在无溶剂和催化剂条件下通过微波辐射制备多种2H-吡喃。该方法具有绿色环保、高产率和短反应时间的优点。十六个化合物（9a-p）通过该过程以良好的至优异的产率获得。
• Brønsted Acid‐Catalyzed Synthesis of Pyrans <i>via</i> a Formal [3+3] Cycloaddition
  作者：Claudie Hubert、Julie Moreau、Jessika Batany、Agathe Duboc、Jean‐Pierre Hurvois、Jean‐Luc Renaud

  DOI：10.1002/adsc.200700375

  日期：2008.1.4

  Brønsted acids catalyze the addition of enolizable β-keto esters to α,β-unsaturated aldehydes leading to substituted 2H-pyrans in good yields under mild conditions via a formal [3+3] cycloaddition.

  布朗斯台德酸通过正规的[3 + 3]环加成反应，在温和的条件下以高收率催化将可烯化的β-酮酯加成到α，β-不饱和醛上，从而以高收率生成取代的2H-吡喃。