1-Oxo-4,6-dimethyl-1H,3H-furo<3,4-c>furan | 124583-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 1-Oxo-4,6-dimethyl-1H,3H-furo<3,4-c>furan
• 英文别名: 4,6-dimethyl-1H,3H-furo[3,4-c]furan-1-one；4,6-dimethyl-1H-furo[3,4-c]furan-3-one
• CAS: 124583-46-6
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: GRUHAYNAVKSLBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Butynyl 2-diazo-3-oxobutanoate 在 rhodium(II) acetate dimer 作用下， 以75%的产率得到1-Oxo-4,6-dimethyl-1H,3H-furo<3,4-c>furan
  参考文献：
  名称：

  Stereo and electronic effects in the rhodium(II)-mediated synthesis of polycyclic lactones and lactams from .alpha.-diazo ester and amide precursors

  摘要：

  The rhodium(II) carboxylate catalyzed decomposition of several alpha-diazo esters and amides has been studied. A series of 5-keto-1-diazo acetates were prepared by acylation of alpha-hydroxy ketones using the (p-toluenesulfonyl)hydrazone of glyoxylic acid chloride. Treatment of these compounds with Rh(II) acetate afforded products derived from carbenoid insertion into solvent. When the hydrogen atom of the diazo carbon was replaced with an electron-withdrawing substituent, smooth cyclization occurred to produce a carbonyl ylide dipole which was subsequently trapped with different dipolarophiles. A series of N-alkyl-2-diazo-3-oxobutylamides, when treated with a catalytic quantity of rhodium(II) acetate, gave furo[3,4-c]furans in good yield. The reaction proceeds via addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. N-Alkynyl-substituted 2-diazoacetamides were also found to cyclize onto the tethered alkyne unit. The resulting rhodium carbenoid can undergo intramolecular and bimolecular cyclopropanation depending on both electronic and conformational factors. Rotamer population of the starting diazoamide was also found to influence product distribution.

  DOI：

  10.1021/jo00069a030

文献信息

• Rhodium(II)-catalyzed cyclization of 2-alkynyl 2-diazo-3-oxobutanoates as a method for synthesizing substituted furans
  作者：Albert Padwa、Frederick R. Kinder

  DOI：10.1021/jo00053a009

  日期：1993.1

  A series of 2-alkynyl 2-diazo-3-oxobutanoates, when treated with a catalytic quantity of rhodium(II) acetate, were found to produce furo[3,4-c]furans in good yield. The reaction proceeds by addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. In a similar manner, indeno[1,2-c]furans were produced from 2-butynyl 2-diazoarylacetates. Compounds substituted with methyl groups on the propargylic carbon atom cyclized at a slower rate. This rate diminution is attributed to the fact that the unsubstituted propargyl group can more easily achieve the required conformation for cyclization. C-H insertion was found to compete with furan formation when an alkyl group was attached to the keto functionality of the starting diazo acetoacetate. Diazo alkynyl sulfones undergo a novel oxygen transfer reaction when treated with rhodium(II) acetate at 80-degrees-C. The cyclized product is formed by sulfone oxygen attack onto the vinyl carbenoid producing a dipolar species which subsequently collapses to give the butenolide sulfoxide.
• Preparation of oxygenated heterocycles via the cyclization reaction of α-diazo substituted alkynes
  作者：Frederick R. Kinder、Albert Padwa

  DOI：10.1016/s0040-4039(00)97184-3

  日期：1990.1
• Generation of vinylcarbenes by the intramolecular addition of .alpha.-diazo ketones to acetylenes
  作者：Albert Padwa、Ugo Chiacchio、Yves Garreau、Jamal M. Kassir、Keith E. Krumpe、Allen M. Schoffstall

  DOI：10.1021/jo00289a006

  日期：1990.1
• PADWA, ALBERT;CHIACCHIO, UGO;GARREAU, YVES;KASSIR, JAMAL M.;KRUMPE, KEITH+, J. ORG. CHEM., 90,(1990) N, C. 414-416
  作者：PADWA, ALBERT、CHIACCHIO, UGO、GARREAU, YVES、KASSIR, JAMAL M.、KRUMPE, KEITH+

  DOI：——

  日期：——
• KINDER, FREDERICK R.;PADWA, ALBERT, TETRAHEDRON LETT., 31,(1990) N7, C. 6835-6838
  作者：KINDER, FREDERICK R.、PADWA, ALBERT

  DOI：——

  日期：——