3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one | 37761-64-1

• 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: 3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 3,3-dimethyl-4,9-dihydro-2H-xanthen-1-one
• CAS: 37761-64-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: CFGJIUPJKYAGEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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-5,5-dimethyl-2-cyclohexen-1-one 在 caesium carbonate 、 三甲基丙酮酸 、 copper(l) chloride 作用下， 反应 7.0h， 以98%的产率得到3,3-dimethyl-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

• Trimethylsilyl Iodide as a Multifunctional Agent in the One-Pot Synthesis of 9-(1H-Indol-3-yl)xanthen-4-(9H)-ones from O-Methyl Protected Salicylaldehydes, Indoles, and β-Dicarbonyl Compounds
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Maryam Nourisefat

  DOI：10.1055/s-0033-1338633

  日期：——

  substitution/cyclization are performed to furnish the target product. The key step in this protocol is the deprotection of the methoxy group by TMSI. Trimethylsilyl iodide (TMSI) is introduced as an efficient reagent for the one-pot synthesis of 9-(1H-indol-3-yl)xanthen-4-(9H)-ones using the reaction of 2-methoxybenzaldehydes (as O-methyl protected salicylaldehydes), indoles, and β-dicarbonyl compounds

  摘要 引入三甲基甲硅烷基碘（TMSI）作为使用2-甲氧基苯甲醛（以O的形式）反应一锅合成9-（1 H-吲哚-3-基）黄嘌呤4-（9 H）-酮的有效试剂-甲基保护的水杨醛），吲哚和β-二羰基化合物。在该方案中，进行一组涉及甲硅烷基化，甲硅烷基烯醇醚形成，甲基脱保护和亲核取代/环化的TMSI反应，以提供目标产物。该协议中的关键步骤是通过TMSI对甲氧基进行脱保护。 引入三甲基甲硅烷基碘（TMSI）作为使用2-甲氧基苯甲醛（以O的形式）反应一锅合成9-（1 H-吲哚-3-基）黄嘌呤4-（9 H）-酮的有效试剂-甲基保护的水杨醛），吲哚和β-二羰基化合物。在该方案中，进行一组涉及甲硅烷基化，甲硅烷基烯醇醚形成，甲基脱保护和亲核取代/环化的TMSI反应，以提供目标产物。该协议中的关键步骤是通过TMSI对甲氧基进行脱保护。
• 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
• 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-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。