2,3,4,9-tetrahydro-1H-xanthen-1-one | 37761-63-0

• 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: 2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 2,3,4,9-tetrahydroxanthen-1-one
• CAS: 37761-63-0
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: SIQUTUHFFSWOFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,9-tetrahydro-1H-xanthen-1-one 在 硼烷四氢呋喃络合物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 以64%的产率得到(R)-2,3,4,9-tetrahydro-1H-xanthen-1-ol
  参考文献：
  名称：

  Lewis酸促进四氢氧杂蒽酮的双键异构化

  摘要：

  本文报道了一种四氢氧杂蒽酮双键异构化的方法。四氢氧杂蒽酮很容易从水杨醛和环烯酮中获得，并在用 AlCl3 处理后发生异构化。研究了产物的异构化机理和后续化学反应。后续化学反应如不对称 Corey-Bakshi-Shibata (CBS) 还原提供了高度官能化的四氢氧杂蒽酮。

  DOI：

  10.1002/ejoc.201201009
• 作为产物：
  描述：

  2-(2-Bromobenzyl)-1,3-cyclohexanedione 在 copper(l) iodide 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  O-Arylation versus C-Arylation:  Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

  摘要：

  The copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls via a six-membered ring closure was examined. With CuI (10 mol %) as the catalyst, N,N'-dimethylethylenediamine as the ligand, and Cs2CO3 as the base, the reactions of alpha-(2-bromobenzyl)-beta-keto esters in THF at refluxing temperature afforded the corresponding substituted 4H-1-benzopyrans in high yields via O-arylation. On the other hand, the reactions of delta-(2-bromophenyl)-beta-keto esters in refluxing dioxane led to the formation of 3,4-dihydronaphthalen-2(1H)-one derivatives via C-arylation.

  DOI：

  10.1021/jo060747t

文献信息

• Facile Approach for the Synthesis of 2,3,4,9-Tetrahydro-1<i>H</i>-xanthen-1-ones and 8,9,10,12-Tetrahydro-11<i>H</i>-benzo[<i>a</i>]xanthen-11-ones via Trapping of <i>o</i>-Quinone Methides
  作者：Vitaly A. Osyanin、Elena A. Ivleva、Yuri N. Klimochkin

  DOI：10.1080/00397911.2010.545164

  日期：2012.6.15

  Abstract An efficient, simple synthesis of 2,3,4,9-tetrahydro-1H-xanthene-1-ones and 8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones is reported by one-pot condensation of 3-dimethylamino-2-cyclohexen-1-ones with hydroxybenzyl alcohols, phenol, and 2-naphthol Mannich bases or their quaternized derivatives. The mechanism of the reaction is believed to involve the formation of the o-quinone methide

  摘要 2,3,4,9-四氢-1H-xanthene-1-ones 和 8,9,10,12-四氢-11H-benzo[a]xanthene-11-ones 的一种高效、简单的合成方法报道了- 3-二甲氨基-2-环己烯-1-酮与羟基苄醇、苯酚和2-萘酚曼尼希碱或其季铵化衍生物的锅缩合。据信该反应的机理涉及邻醌甲基化物中间体的形成。图形概要
• 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。
• An unusual Me₃SiI-promoted [4+2] annulation and reduction: an efficient approach to construct 4H-benzopyrans
  作者：Feijun Wang、Mingliang Qu、Feng Chen、Li Li、Min Shi

  DOI：10.1039/c1cc16028a

  日期：——

  Me3SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct 4H-benzopyrans in moderate to good yields. This tandem reaction proceeds with high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization.

  Me3SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct 4H-benzopyrans in moderate to good yields. This tandem reaction proceeds with high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization.
• 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%.