2,3-dihydrocyclopenta[b]chromen-1(9H)-one | 37761-68-5

• 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: 2,3-dihydrocyclopenta[b]chromen-1(9H)-one
• 英文别名: 3,9-dihydro-2H-cyclopenta[b]chromen-1-one；3,9-dihydro-2H-cyclopenta[b]chromen-1-one
• CAS: 37761-68-5
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: AAXXHLDOOVKBTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(2-bromophenyl)methyl]-3-hydroxy-2-cyclopenten-1-one 在 caesium carbonate 、 三甲基丙酮酸 、 copper(l) chloride 作用下， 反应 7.0h， 以54%的产率得到2,3-dihydrocyclopenta[b]chromen-1(9H)-one
  参考文献：
  名称：

  Copper(I)-Catalyzed Intramolecular O-Arylation for the Synthesis of 2,3,4,9-Tetrahydro-1H-xanthen-1-ones with Low Loads of CuCl

  摘要：

  As little as 0.5 mol % CuCl is sufficient to catalyze the intramolecular O-arylation of easily accessible 2-(2-bromobenzyl)cyclohexane-1,3-diones to provide the corresponding 2,3,4,9-tetrahydro-1H-xanthen-1-ones with yields ranging from 83% to 99%.

  DOI：

  10.1021/jo3018318

文献信息

• Multi-catalysis reactions: direct organocatalytic sequential one-pot synthesis of highly functionalized cyclopenta[b]chromen-1-ones
  作者：Dhevalapally B. Ramachary、Y. Vijayendar Reddy、Mamillapalli Kishor

  DOI：10.1039/b812551a

  日期：——

  We have developed a new technology called multi-catalysis for the sequential one-pot synthesis of highly functionalized heterocycles. A practical and novel multi-component aniline-, self- and Brønsted acid-catalyzed selective process for the sequential one-pot synthesis of highly substituted 2-(2-hydroxy-aryl)-cyclopentane-1,3-diones, 3,9-dihydro-2H-cyclopenta[b]chromen-1-ones and 3,3-dimethyl-2,3,4,9-tetrahydro-xanthen-1-ones is reported. Direct combination of aniline- and self-catalyzed cascade olefination–hydrogenation (O–H) and Brønsted acid-catalyzed cascade oxy-Michael–dehydration (OM–DH) of 1,3-diones, salicylic aldehydes and organic-hydrides is developed in one-pot to furnish the highly functionalized 3,9-dihydro-2H-cyclopenta[b]chromen-1-ones and 3,3-dimethyl-2,3,4,9-tetrahydro-xanthen-1-ones with high yields.

  我们开发了一种名为 "多催化"（multi-catalysis）的新技术，用于高官能度杂环的顺序式一次锅合成。报告了一种实用而新颖的多组分苯胺、自催化和布氏酸催化选择性工艺，用于高取代度的 2-(2-羟基芳基)-环戊烷-1,3-二酮、3,9-二氢-2H-环戊二烯并[b]色烯-1-酮和 3,3-二甲基-2,3,4,9-四氢-氧杂蒽-1-酮的顺序一锅合成。将苯胺和自催化级联烯化-氢化（O-H）与布氏酸催化级联氧-迈克尔-脱水（OM-DH）直接结合在一起、在水杨醛和有机酐的催化下，以一锅法生成高产率的高度官能化的 3,9-二氢-2H-环戊并[b]色烯-1-酮和 3,3-二甲基-2,3,4,9-四氢-氧杂蒽-1-酮。
• Copper-Catalysed One-Pot Synthesis of 2,3,4,9-Tetrahydro-1H-Xanthen-1-Ones from 2-Halobenzylbromides and Cyclic-1,3-Diketones in Water
  作者：Zuxing Mao、Xinhai Zhu、Yiqian Wan

  DOI：10.1007/s10562-015-1538-z

  日期：2015.8

  A simple, environmentally friendly, tandem C-benzylation and intramolecular O-arylation for the sequential one-pot synthesis of functionalised 4H-chromenes is reported. The reactions between 2-halobenzylbromides and cyclic-1,3-diketones were catalysed by CuO/oxalohydrazide/hexane-2,5-dione in water to produce 2,3,4,9-tetrahydro-1H-xanthen-1-ones in moderate to high yields.A simple, environmental friendly, tandem C-benzylation and intramolecular O-arylation for the sequential one-pot synthesis of 2,3,4,9-tetrahydro-1H-xanthen-1-ones in water is described.