4',4',6,6-tetramethyl-3-propyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione | 1152293-69-0

• 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: 4',4',6,6-tetramethyl-3-propyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione
• 英文别名: 4',4',6,6-tetramethyl-3-propyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1'-cyclohexane]-2',4,6'-trione；5',5',6,6-tetramethyl-3-propylspiro[5,7-dihydro-3H-1-benzofuran-2,2'-cyclohexane]-1',3',4-trione
• CAS: 1152293-69-0
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: ARTBBYIIFRIZNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  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 2.4h， 生成 4',4',6,6-tetramethyl-3-propyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),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

• 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。
• 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。
• 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。
• 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。