四氢呋喃[2,3-B]呋喃-2(6AH)-酮 | 104223-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 中文名称: 四氢呋喃[2,3-B]呋喃-2(6AH)-酮
• 英文名称: hexahydro furo<2,3-b>furan-2-one
• 英文别名: (+/-)-tetrahydrofuro[2,3-b]furan-2-one；Hexahydrofuro[2,3-b]furan-2-one；3,3a,4,6a-tetrahydro-2H-furo[2,3-b]furan-5-one
• CAS: 104223-37-2
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: IADWRRHAUNBWTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢呋喃[2,3-B]呋喃-2(6AH)-酮 在 palladium on activated charcoal trityl perchlorate 、 水 、 氢气 、 叔丁基锂 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 臭氧 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 、 苯 为溶剂， 反应 125.58h， 生成 (3R,4S,4aR,2'S,3a'R,6a'S)-3,4,4a,5,6,7-hexahydro-4-(hexahydrofuro[2,3-b]furan-2'-yl)-3,4-dimethyl-2H-naphthalen-1-one
  参考文献：
  名称：

  Total Synthesis of Dihydroclerodin from (R)-(−)-Carvone

  摘要：

  The first total synthesis of the natural enantiomer of the insect-antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3-b]furan moiety was introduced in an early stage of the synthesis. The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

  DOI：

  10.1021/jo991151r
• 作为产物：
  描述：

  (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)acetonitrile 在 sodium hydroxide 、 盐酸 作用下， 反应 4.0h， 以91%的产率得到四氢呋喃[2,3-B]呋喃-2(6AH)-酮
  参考文献：
  名称：

  Total Synthesis of Dihydroclerodin from (R)-(−)-Carvone

  摘要：

  The first total synthesis of the natural enantiomer of the insect-antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3-b]furan moiety was introduced in an early stage of the synthesis. The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

  DOI：

  10.1021/jo991151r

文献信息

• SALT AND PHOTORESIST COMPOSITION CONTAINING THE SAME
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20170247323A1

  公开（公告）日：2017-08-31

  A salt having a group represented by the formula (aa): wherein X a and X b independently each represent an oxygen atom or a sulfur atom, the ring W represents a C3-C36 heterocyclic ring which has an ester bond or a thioester bond, said heterocyclic ring optionally further having an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group each by which a methylene group has been replaced, and said heterocycilic ring optionally having a hydroxyl group, a cyano group, a carboxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C2-C13 alkoxycarbonyl group, a C2-C13 acyl group, a C2-C13 acyloxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or any combination of these groups each by which a hydrogen atom has been replaced, and * represents a binding position.

  一种盐，其具有由公式（aa）表示的基团：其中Xa和Xb独立地代表一个氧原子或一个硫原子，环W代表一个具有酯键或硫酯键的C3-C36杂环环，该杂环环还可以进一步具有一个氧原子、一个硫原子、一个羰基或一个磺酰基，其中每个都已被一个亚甲基取代，该杂环环还可以具有一个羟基、一个氰基、一个羧基、一个C1-C12烷基、一个C1-C12烷氧基、一个C2-C13烷氧羰基、一个C2-C13酰基、一个C2-C13酰氧基、一个C3-C12脂环烃基、一个C6-C10芳香烃基或任何组合，其中每个都已被氢原子取代，*表示一个结合位置。
• Synthesis and oxidative rearrangement of selenenylated dihydropyrans
  作者：Sébastien Redon、Xavier Pannecoucke、Xavier Franck、Francis Outurquin

  DOI：10.1039/b718825k

  日期：——

  Selenenylated dihydropyrans prepared by inverse demand hetero-Diels–Alder reactions undergo oxidative rearrangement when treated with H2O2, leading to tetrahydrofuran-2-ones by ring contraction.

  通过逆需求异狄尔斯-阿尔德反应制备的硒化二氢吡喃在用 H2O2 处理时会发生氧化重排，通过环收缩生成四氢呋喃-2-酮。
• Furo[2,3-b]pyran-2-one compounds and process for preparation thereof
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US10941155B2

  公开（公告）日：2021-03-09

  The present invention discloses a novel furo[2,3-b]pyran-2-one compound of formula (I) and a single step process for the preparation of furo[2,3-b]pyran-2-ones using Lewis acid-promoted cascade annulation of alkynols and α-ketoesters.

  本发明公开了一种新颖的式 (I) 呋喃并[2,3-b]吡喃-2-酮化合物，以及使用路易斯酸促进的炔醇和 α 酮酯级联环化法制备呋喃并[2,3-b]吡喃-2-酮的一步法工艺。
• Stannyl ester cyclizations
  作者：George A. Kraus、Kevin Landgrebe

  DOI：10.1016/s0040-4020(01)97182-0

  日期：1985.1
• KRAUS, G. A.;LANDGREBE, K., TETRAHEDRON LETT., 1984, 25, N 36, 3939-3942
  作者：KRAUS, G. A.、LANDGREBE, K.

  DOI：——

  日期：——

表征谱图