3-(4-fluorophenyl)-4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione | 1193374-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(4-fluorophenyl)-4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione
• 英文别名: 3-(4-fluorophenyl)-5',5',6,6-tetramethylspiro[5,7-dihydro-3H-1-benzofuran-2,2'-cyclohexane]-1',3',4-trione
• CAS: 1193374-95-6
• 化学式: C₂₃H₂₅FO₄
• 分子量: 384.448
• InChiKey: WEKSGHFEQXETCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 2.23h， 生成 3-(4-fluorophenyl)-4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione
  参考文献：
  名称：

  微波辐射下基于碘鎓盐的三组分新反应导致2-螺取代的二氢呋喃

  摘要：

  在微波辐射下，已经开发了一种新的基于碘鎓内鎓盐的三组分反应，该反应可从容易获得的普通反应物开始合成高度官能化的2-螺取代的二氢呋喃。该过程很容易，避免了耗时且昂贵的合成，繁琐的前体处理和纯化以及对官能团的保护/脱保护。该方法由于反应时间短且易于加工而非常有效，为构建多取代的螺二氢呋喃骨架提供了有效的策略。

  DOI：

  10.1002/jhet.1732

文献信息

• A pseudo multi-component electrochemical synthesis of spiro dihydrofuran derivatives
  作者：Changsheng Yao、Ying Wang、Tuanjie Li、Chenxia Yu、Liang Li、Chao Wang

  DOI：10.1016/j.tet.2013.10.056

  日期：2013.12

  An electrochemical strategy to the assembly of tricyclic spiro dihydrofuran scaffold via the reaction of aryl aldehyde and dimedone has been developed successfully. This protocol has the advantages of high yields, wide application scope and an environmental benign procedure compared with the reported methods.

  已成功开发了一种通过芳基醛与二甲酮反应组装三环螺二氢呋喃骨架的电化学方法。与已报道的方法相比，该方案具有收率高，适用范围广，环境友好的优点。
• Single-Pot Synthesis of Spiroannulated Dihydrofurans by Iodine–Ammonium Acetate–Mediated Reaction of Dimedone with Aldehydes
  作者：Devi Prasad Sahu、Santosh Kumar Giri、Vandana Varshney、Shailesh Kumar

  DOI：10.1080/00397910902763938

  日期：2009.9.8

  Abstract Iodine–ammonium acetate–mediated annealation of dimedone with aldehydes led to facile formation of spirodihydrofuran in good yields through tandem Knoevenagel–Michael iodonation and cyclodehydroiodonation reactions in a single pot.

  摘要 碘-乙酸铵介导的二甲酮与醛的退火导致通过串联 Knoevenagel-Michael 碘化和环脱氢碘化反应在一个锅中以良好的产率轻松形成螺二氢呋喃。
• Selective synthesis of spiro and dispiro compounds using Mn(III)-based oxidation of tetracarbonyl compounds
  作者：Suzuka Yokote、Satomi Nishikawa、Keisuke Shibuya、Kazuki Hisano、Hiroshi Nishino

  DOI：10.1016/j.tet.2020.131165

  日期：2020.5

  The Mn(III)-based oxidation of methylenebis(cyclohexanedione)s and methylenebis(piperidinedione)s as a tetracarbonyl compound was investigated under various conditions, selectively producing spiro dihydrofurans and dispiro cyclopropanes depending on the solvent. The mechanism for the formation of the spiro dihydrofurans and dispiro cyclopropanes was discussed. In addition, a simple synthesis of a new

  在各种条件下研究了作为四羰基化合物的亚甲基双（环己烷二酮）和亚甲基双（哌啶二酮）的Mn（III）基氧化，根据溶剂选择性生产螺二氢呋喃和二螺环丙烷。讨论了螺二氢呋喃和双螺环丙烷的形成机理。此外，一种新型生物碱3,4,6,7,8,10-六氢-1 H-吡喃并[3,2- c：5,6- c' ]二吡啶-1,9的简单合成证明了（2 H）-二酮。
• Synthesis of dioxapropellanes using Mn(III)-based oxidative tandem cyclization of tetracarbonyl compounds with diarylethenes
  作者：Keisuke Shibuya、Ayaka Chikamatsu、Kazuki Hisano、Hiroshi Nishino

  DOI：10.1093/bulcsj/uoae011

  日期：2024.3.1

  The Mn(III)-based oxidation of tetracarbonyl compounds with 1,1-diarylethenes formed dioxapropellanes. The use of methylenebis(3-hydroxycyclohex-2-en-1-one)s as a tetracarbonyl compound led to the production of 3,4,5,6,7,9-hexahydro-8H-4a,9a-(epoxyethano)xanthene-1,8(2H)-diones in good yields. Although the reaction competed with self-cyclization to form 3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1′-cyclohexane]-2′,4,6′-triones, it could be controlled by adding the co-solvent formic acid at room temperature. The reactions of alkyl- and aryl-substituted methylenebis(3-hydroxycyclohex-2-en-1-one)s resulted in the corresponding dioxapropellanes as a diastereomixture. The formation of diastereomers is explained by the steric hindrance of the intermediate carbocations during tandem cyclization. The reactions using 2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)butane-1,4-diones and 2,2′-methylenebis(3-hydroxycyclopent-2-en-1-one)s also produced the corresponding dioxapropellanes. The structure determination of the products and the reaction pathway for the formation of dioxapropellanes are discussed.

  摘要 基于锰（III）的四羰基化合物与 1,1-二叔丁烯的氧化反应生成了二氧丙环。使用亚甲基双（3-羟基环己-2-烯-1-酮）作为四羰基化合物，可以生产出 3,4,5,6,7,9-六氢-8H-4a,9a-(环氧乙烷)氧杂蒽-1,8(2H)-二酮，收率很高。虽然该反应与自环化反应竞争生成 3,5,6,7-四氢-4H-螺[苯并呋喃-2,1′-环己烷]-2′,4,6′-三酮，但在室温下加入辅助溶剂甲酸可以控制反应。烷基和芳基取代的亚甲基双（3-羟基环己-2-烯-1-酮）反应生成相应的非对映混合物二氧丙环。形成非对映异构体的原因是串联环化过程中中间碳位的立体阻碍。使用 2-(2-羟基-4,4-二甲基-6-氧代环己-1-烯-1-基)丁烷-1,4-二酮和 2,2′-亚甲基双(3-羟基环戊-2-烯-1-酮)的反应也产生了相应的二氧杂环丙烷。本文讨论了生成物的结构测定和二氧杂环戊烷的生成反应途径。
• A New Iodonium Ylide-Based Three-Component Reaction Leading to 2-Spirosubstituted Dihydrofurans under Microwave Irradiation
  作者：Xing-Chao Tu、Yan Yu、Man-Su Tu、Bo Jiang、Chao Li、Shu-Jiang Tu

  DOI：10.1002/jhet.1732

  日期：2014.3

  A new iodonium ylide‐based three‐component reaction for the synthesis of highly functionalized 2‐spirosubstituted dihydrofurans starting from readily available common reactants has been developed under microwave irradiation. The procedure is facile, avoiding time‐consuming and costly syntheses, tedious work‐up and purifications of precursors as well as protection/deprotection of functional groups.

  在微波辐射下，已经开发了一种新的基于碘鎓内鎓盐的三组分反应，该反应可从容易获得的普通反应物开始合成高度官能化的2-螺取代的二氢呋喃。该过程很容易，避免了耗时且昂贵的合成，繁琐的前体处理和纯化以及对官能团的保护/脱保护。该方法由于反应时间短且易于加工而非常有效，为构建多取代的螺二氢呋喃骨架提供了有效的策略。