9H-占吨-9-酮,1,2,3-三甲氧基- | 27460-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 9H-占吨-9-酮,1,2,3-三甲氧基-
• 英文名称: 1,2,3-trimethoxy-9H-xanthen-9-one
• 英文别名: 6,7,8-trimethoxyxanthone；1,2,3-trimethoxy-xanthen-9-one；1,2,3-Trimethoxyxanthen-9-one
• CAS: 27460-10-2
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: CQDQINXEWIRADS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  2-氟苯腈 在 氢氧化钾 、 potassium fluoride on basic alumina 、 甲烷磺酸 、 18-冠醚-6 、 双氧水 、 phosphorus pentoxide 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 132.0h， 生成 9H-占吨-9-酮,1,2,3-三甲氧基-
  参考文献：
  名称：

  Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹

  摘要：

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.

  DOI：

  10.1021/jo980800g

文献信息

• Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
  作者：Hashim F. Motiwala、Rakesh H. Vekariya、Jeffrey Aubé

  DOI：10.1021/acs.orglett.5b02851

  日期：2015.11.6

  Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential

  芳基烷基酰氯在1,1,1,3,3,3-六氟-2-丙醇中的简单溶解可促进分子内Friedel-Crafts酰化反应，而无需其他催化剂或试剂。该反应在操作和产物分离上都操作上很简单（只需要浓缩后再纯化），并适用于各种各样的底物。据报道涉及潜在反应机理的初步研究。
• Synthesis of Xanthones via Copper(II)-Catalyzed Dehydrogenative Cyclization and Successive Aromatization in a One-Step Sequence
  作者：Yoon Hu Jang、Yo-Sep Yang、Seung Hwan Son、Hyung-Seok Yoo、Jeong-Won Shin、Hyuck-Jae Won、Soo Lim Kim、Changjin Lim、Nam-Jung Kim

  DOI：10.1021/acs.orglett.2c03730

  日期：2022.12.23
• US5741813A
  申请人：——

  公开号：US5741813A

  公开（公告）日：1998-04-21
• US5981774A
  申请人：——

  公开号：US5981774A

  公开（公告）日：1999-11-09
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.