3-methyl-2,3,4,9-tetrahydro-1H-xanthen-1-one | 1407096-48-3

• 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: 3-methyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 3-Methyl-2,3,4,9-tetrahydroxanthen-1-one；3-methyl-2,3,4,9-tetrahydroxanthen-1-one
• CAS: 1407096-48-3
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: QZMHXYLQOQBRME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-5-methyl-2-cyclohexen-1-one 在 caesium carbonate 、 三甲基丙酮酸 、 copper(l) chloride 作用下， 反应 7.0h， 以92%的产率得到3-methyl-2,3,4,9-tetrahydro-1H-xanthen-1-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

• Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions
  作者：Akanksha M. Pandey、Naveen Kumar Digrawal、Nirmala Mohanta、Akash Bandu Jamdade、Moreshwar B. Chaudhari、Girish Singh Bisht、Boopathy Gnanaprakasam

  DOI：10.1021/acs.joc.1c00714

  日期：2021.7.2

  base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis of N-heterocycles by using 1,3-dicarbonyls and amino alcohols through a domino sequential enamine formation and intramolecular oxidative cyclization strategy. This unified approach is also applicable for the synthesis of O-heterocycles involving 2-hydroxybenzyl alcohol as a coupling reactant via consecutive

  开发了一种无碱和无受体的 Ru 催化脱氢方法，通过多米诺顺序烯胺形成和分子内氧化环化策略，使用 1,3-二羰基和氨基醇合成N-杂环。这种统一的方法也适用于通过连续的 C-烷基化和分子内环化步骤合成 2-羟基苯甲醇作为偶联反应物的 O-杂环。本协议适用于各种重要的生物学支架的合成，如四氢-4 H -indol-4-one、3,4-dihydroacridin-1(2 H )-one 和四氢-1 H - xanthen-使用单一催化系统的 1-ones 衍生物，即。RuH 2CO(PPh 3 ) 3。对环境无害的 H 2 O 和 H 2是该多米诺骨牌过程中唯一的副产品。此外，该报告还描述了使用醇作为烷基化伙伴的RuH 2 CO(PPh 3 ) 3 -催化的四氢-4 H-吲哚-4-酮的C3-烷基化。首次证明了无受体脱氢环化的无溶剂克级反应。一些实验研究和光谱证据为 Ru 催化的氨基醇或 2-羟基
• Copper-catalyzed tandem reaction of 2-bromobenzyl bromides with 1,3-dicarbonyl compounds leading to 4H-chromenes
  作者：Xin Ying Zhang、Liang Liang Fang、Nan Liu、Hua Yue Wu、Xue Sen Fan

  DOI：10.1016/j.cclet.2012.08.005

  日期：2012.10

  A Cu(I)-catalyzed one-pot tandem reaction of 2-bromobenzyl bromides with 1,3-dicarbonyl compounds leading to 4H-chromene derivatives has been developed. This new approach toward 4H-chromenes combines several reactions in one pot and builds molecular complexity from readily available starting materials.

  已开发出Cu（I）催化的2-溴苄基溴与1,3-二羰基化合物的一锅串联反应，从而导致4 H-色烯衍生物。这种针对4 H-苯甲基的新方法可在一锅中将多个反应结合在一起，并从易于获得的起始原料中增强分子的复杂性。
• 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.
• Copper(I)-Catalyzed Intramolecular O-Arylation for the Synthesis of 2,3,4,9-Tetrahydro-1<i>H</i>-xanthen-1-ones with Low Loads of CuCl
  作者：Kavitha Sudheendran、Chandi C. Malakar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/jo3018318

  日期：2012.11.16

  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%.