2-benzoyl-6,6-dimethyl-4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzo[b]furan

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-6,6-dimethyl-4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzo[b]furan
• 英文别名: 2-benzoyl-3,5,6,7-tetrahydro-6,6-dimethyl-3-phenyl-1-benzofuran-4(2H)-one；trans-2-benzoyl-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydrobenzofuran-4(2H)-one；6,6-dimethyl-2-benzoyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one；2-benzoyl-6,6-dimethyl-3-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；(+/-)-trans-2-benzoyl-6,6-dimethyl-3-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；trans-2-benzoyl-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one；(2S,3S)-2-benzoyl-6,6-dimethyl-3-phenyl-2,3,5,7-tetrahydro-1-benzofuran-4-one
• 化学式: C₂₃H₂₂O₃
• 分子量: 346.426
• InChiKey: VHQHAGXMYIMQOW-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyl-6,6-dimethyl-4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzo[b]furan 在 三氢化钐 、 三甲基氯硅烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以63%的产率得到7,7-dimethyl-2,4-diphenyl-4,6,7,8-tetrahydro-5H-chromen-5-one
  参考文献：
  名称：

  2-酰基-2,3-二氢呋喃的两步序列多组分合成/还原重排用于环状4H-吡喃的模块化组装

  摘要：

  各种反式-2-酰基-2,3-二氢呋喃已由易于获得的结构多样的前体组装而成，然后在 Sm/TMSCl 或 Zn/ZrCl 4氧化还原系统的作用下重新排列成一系列环状4 H-吡喃。目前的合成序列被认为是杂-和碳-稠合 4 H-吡喃的模块化方法。重排涉及羰基的 SET 还原为卡宾，然后是罕见的 [1,2]-芳氧基转移。使用 Zn/ZrCl 4氧化还原系统丰富了合成工具栏。

  DOI：

  10.1002/adsc.202100261
• 作为产物：
  描述：

  5,5-dimethyl-2-(1,3-diphenyl-3-oxopropyl)-1,3-cyclohexanedione 在 亚碘酰苯 、 四丁基碘化铵 作用下， 以 水 为溶剂， 反应 16.0h， 以70%的产率得到2-benzoyl-6,6-dimethyl-4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzo[b]furan
  参考文献：
  名称：

  碘（III）介导的立体选择性氧化环化反应，用于合成功能化的熔融二氢呋喃衍生物

  摘要：

  由碘代苯与碘化四（正丁基）铵的结合介导的有效的水性氧化环化提供了一种新的方便且有用的途径，以中等至极好的收率和高的非对映选择性来官能化稠合的二氢呋喃衍生物。

  DOI：

  10.1021/jo902553k

文献信息

• 2,3-Dihydrofurans as Potential Cytotoxic and Antibacterial Agents: Tandem Knoevenagel−Michael Cyclization for the Synthesis of 2,3-Dihydrofurans by Using α-Tosyloxy Ketone Precursors
  作者：Jajula Kashanna、Rathod Aravind Kumar、Ravada Kishore、Duddukuri Nandan Kumar、Alleni Suman Kumar

  DOI：10.1002/cbdv.201800277

  日期：2018.11

  Novel 2,3‐dihydrofuran derivatives were synthesized through a tandem Knoevenagel−Michael cyclization in good yield by reacting α‐tosyloxy ketone, 5,5‐dimethyl‐1,3‐cyclohexanedione, and various aldehydes in the presence of phthalazine in acetonitrile. These compounds were subjected to in vitro antibacterial screening against eight micro‐organisms by using diffusion method and also in vitro cytotoxicity

  α-甲苯磺酰氧基酮、5,5-二甲基-1,3-环己二酮和各种醛在乙腈中存在酞嗪的情况下，通过串联 Knoevenagel-Michael 环化反应合成了新型 2,3-二氢呋喃衍生物。使用扩散法对这些化合物进行了针对八种微生物的体外抗菌筛选，并通过应用 MTT 法对四种人癌细胞系进行了体外细胞毒性筛选。一些化合物显示出令人印象深刻的活性。
• Geminally activated β-nitrostyrenes in reactions with cyclic β-diketones
  作者：V. M. Berestovitskaya、R. I. Baichurin、L. V. Baichurina、A. V. Fel’gendler、N. I. Aboskalova

  DOI：10.1134/s1070363213090211

  日期：2013.9

  gem-alkoxycarbonylnitroethenes with cyclic β-diketones (dihydroresorcinol and dimedone) occurs as a one-pot process via sequential AdN and SN steps followed by denitration to give functionally substituted hexahydrobenzofurans. The intermediate products of the nucleophilic addition have been isolated in the reactions of gem-acetylnitroethenes with dihydroresorcinol. The structures of the synthesized compounds

  宝石-苯甲酰基硝基乙烯和宝石-烷氧基羰基硝基乙烯与环状β-二酮（二氢间苯二酚和二甲酮）的相互作用是通过顺序的Ad N和S N步骤进行一锅法过程，然后进行反硝化生成功能取代的六氢苯并呋喃。亲核加成的中间产物已经在宝石-乙酰基硝基乙烯与二氢间苯二酚的反应中分离出。合成化合物的结构已通过IR，1 H和13 C- 1 H}光谱学证实，其中包括异核相关实验（1 H- 13 C HMQC和1 H- 13 C HMBC）。
• Base-controlled selective construction of polysubstituted dihydrofuran and furan derivatives through an I2-mediated cyclization
  作者：Chun-Bao Miao、Rui Liu、Yan-Fang Sun、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1016/j.tetlet.2016.12.078

  日期：2017.2

  A base-controlled formal [3 + 2] cycloaddition of 1,3-dicarbonyl compounds to enones via an I-2-mediated cyclization was reported. Highly functionalized dihydrofurans and furans were selectively obtained under I-2/DMAP and I-2/DBU conditions in the cyclization step, respectively. (C) 2016 Elsevier Ltd. All rights reserved.
• CAN-promoted, diastereoselective synthesis of fused 2,3-dihydrofurans and their transformation into tetrahydroindoles
  作者：Swarupananda Maiti、Paramasivan T. Perumal、J. Carlos Menéndez

  DOI：10.1016/j.tet.2010.10.017

  日期：2010.12

  The reaction between 1 3-cyclohexanediones and chalcones (or their vinilogs) in the presence of 2 5 equiv of cerium(IV) ammonium nitrate afforded trans-2-arylcarbonyl-3-aryl (or styryl)-2 3 6 7-tetrahydrobenzofuran-4(5H)-ones in good to excellent yields and in high diastereoselectivities The method was also extended to the preparation of derivatives of the 5 6-dihydro-2H-cyclopenta[b]furan-4(3H)-one system The fused 2 3-dihydrofuran derivatives were transformed into 1-alkyl-2-acyl-3-aryl-6 7-dihydroindole-4(5H)-ones by 2 3-dehydrogenation followed by reaction with primary amines The direct reaction of the tetrahydrobenzofuran-4(5H)-one compounds derived from dimedone with amines gave 1-alkyl-2-alkylimino-3-aryl-6 7-dihydroindole-4(5H)-ones while starting materials derived from 1 3-cyclohexanedione underwent an unprecedented 2-deacylation reaction and gave 1-alkyl-3-aryl-6 7-dihydroindole-4(5H)-ones (C) 2010 Elsevier Ltd All rights reserved
• A facile domino protocol for the stereoselective synthesis of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines
  作者：Beermohamed Vinosha、Subbu Perumal、Subbiah Renuga、Abdulrahman I. Almansour

  DOI：10.1016/j.tetlet.2011.12.047

  日期：2012.2

  A facile protocol for the stereoselective construction of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines from the reactions of 2,2'-sulfonylbis(1,3-diarylprop-2-en-1-ones) with cyclic 1,3-diketones, viz. cyclohexane-1,3-diones, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)-dione in the presence of DBU in ethanol is described. This transformation presumably occurs via domino Michael addition-proton exchange-annulation via intramolecular displacement sequence. (C) 2011 Elsevier Ltd. All rights reserved.