4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione | 118966-45-3

• 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: 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione
• 英文别名: 4',4',6,6-tetramethyl-3-(4-tolyl)-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione；4',4',6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'(5H)-trione；4',4',6,6-tetramethyl-3-(p-tolyl)-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione；3-(4-methylphenyl)-4’,4’,6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’-trione；spiro[(6,6-dimethyl-3-(4-methylphenyl)-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran)-2,2'-(5,5-dimethylcyclohexane-1,3-dione)]；4',4',6,6-tetramethyl-3-(4-methylphenyl)-3,5,6,7-tetrahydro-4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-trione；5',5',6,6-tetramethyl-3-(4-methylphenyl)spiro[5,7-dihydro-3H-1-benzofuran-2,2'-cyclohexane]-1',3',4-trione
• CAS: 118966-45-3
• 化学式: C₂₄H₂₈O₄
• 分子量: 380.484
• InChiKey: WVLQNKYXNUPSTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  233 °C
• 沸点：
  560.3±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(4-methylphenyl)methyl]-5,5-dimethylcyclohex-2-en-1-one 在 manganese(III) triacetate dihydrate 作用下， 以 甲酸 、 溶剂黄146 为溶剂， 反应 0.08h， 以89%的产率得到4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione
  参考文献：
  名称：

  使用基于锰（III）的四羰基化合物氧化选择性合成螺和双螺化合物

  摘要：

  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。

  DOI：

  10.1016/j.tet.2020.131165

文献信息

• 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。
• 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。
• Synthesis of Spiro‐dihydrofuran in the Presence of a Novel and Reusable Nanocatalyst Cu (II)‐Glycerol/MCM‐41
  作者：Hana Batmani、Nader Noroozi Pesyan、Forugh Havasi、Michael Aalinejad

  DOI：10.1002/aoc.4997

  日期：2019.8

  The use of supported Cu complex on mesoporous as a novel, efficient, heterogeneous, reusable and green catalyst for the synthesis of spiro‐dihydrofuran derivatives is reported. This methodology is effective for the reaction of dimedone with a wide range of aldehyde in the presence of BrCN and triethylamine. The structure of catalyst was characterized by different techniques such as EDX, SEM, TGA, ICP‐OES

  据报道，在介孔上负载的铜配合物是一种新颖，高效，多相，可重复使用的绿色催化剂，可用于合成螺二氢呋喃衍生物。该方法对于在BrCN和三乙胺存在下二甲酮与各种醛的反应有效。催化剂的结构通过EDX，SEM，TGA，ICP-OES，XRD，TEM，FT-IR和BET等不同技术表征。循环使用的纳米催化剂至少使用了五次，活性没有明显降低。
• Selective formation of spiro dihydrofurans from one-pot reaction of dimedone with BrCN and aldehydes in the presence of Et3N
  作者：Nader Noroozi Pesyan、Alireza Shokr、Mohammad Behroozi、Ertan Şahin

  DOI：10.1007/s13738-012-0190-4

  日期：2013.6

  Reaction of 5,5-dimethylcyclohexane-1,3-dione (dimedone), aldehydes and cyanogen bromide in the presence of triethylamine leads to the selective formation of spiro dihydrofurans in moderate to good yields at room temperature.

  在三乙胺存在下，5,5-二甲基环己烷-1,3-二酮（二甲酮），醛和溴化氰的反应在室温下以中等至良好的产率选择性生成螺二氢呋喃。