4',4',6,6-tetramethyl-3-(thiophen-2-yl)-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione | 342391-77-9

• 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-(thiophen-2-yl)-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione
• 英文别名: 4',4',6,6-tetramethyl-3-(thiophen-2-yl)-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione；5',5',6,6-tetramethyl-3-thiophen-2-ylspiro[5,7-dihydro-3H-1-benzofuran-2,2'-cyclohexane]-1',3',4-trione
• CAS: 342391-77-9
• 化学式: C₂₁H₂₄O₄S
• 分子量: 372.485
• InChiKey: LKAGJPVHHCCWHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2'-(thiophen-2-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) 在 manganese(III) triacetate dihydrate 作用下， 以 溶剂黄146 为溶剂， 反应 0.02h， 以32%的产率得到4',4',6,6-tetramethyl-3-(thiophen-2-yl)-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-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。
• Selective Formation of Spiro Dihydrofurans and Cyclopropanes Through Unexpected Reaction of Aldehydes with 1,3-Dicarbonyl Compounds
  作者：Guan-Wu Wang、Jie Gao

  DOI：10.1021/ol900451d

  日期：2009.6.4

  5-dimethylcyclohexane-1,3-dione and 1,3-indandione to selectively afford spiro dihydrofuran and cyclopropane derivatives, promoted by molecular iodine and dimethylaminopyridine under mechanical milling conditions, has been demonstrated. The products were obtained in good to excellent yields. A possible mechanism of this unusual reaction process is proposed.

  在机械研磨条件下，由分子碘和二甲基氨基吡啶促进的各种醛与5,5-二甲基环己烷-1,3-二酮和1,3-茚满二酮的氧化加成反应以选择性提供螺二氢呋喃和环丙烷衍生物的有效方法已具有被证明。获得的产物具有良好至优异的产率。提出了这种异常反应过程的可能机理。
• 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。