2,3,3a,4-tetrahydro-2-oxonaphtho<2,3-b>furan | 136911-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2,3,3a,4-tetrahydro-2-oxonaphtho<2,3-b>furan
• 英文别名: 3a,4-dihydronaphtho[2,3-b]furan-2(3H)-one；3a,4-dihydro-3H-benzo[f][1]benzofuran-2-one
• CAS: 136911-08-5
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: JVIWHQVWMOPSBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,3a,4-tetrahydro-2-oxonaphtho<2,3-b>furan 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以37%的产率得到3,3a-didehydro-2,3,3a,4,9,9a-hexahydro-2-oxo-1H-benzindene
  参考文献：
  名称：

  Total synthesis of a novel antiulcer agent via a modification of the intramolecular Wadsworth-Emmons-Wittig reaction

  摘要：

  DOI：

  10.1021/ja00312a028
• 作为产物：
  描述：

  2-烯丙基苄醇 在 bis-triphenylphosphine-palladium(II) chloride N-氯代丁二酰亚胺 、 二甲基硫 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 100.0 ℃ 、4.14 MPa 条件下， 反应 38.0h， 生成 2,3,3a,4-tetrahydro-2-oxonaphtho<2,3-b>furan
  参考文献：
  名称：

  Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio

  摘要：

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.

  DOI：

  10.1016/s0040-4020(01)80765-1

文献信息

• A New Route to γ-Arylidenebutyrolactones via a tandem carbopalladation-heterocyclisation sequence: a formal synthesis of U-68,215
  作者：Marcello Cavicchioli、Sylvie Decortiat、Didier Bouyssi、Jacques Goré、Geneviève Balme

  DOI：10.1016/0040-4020(96)00637-0

  日期：1996.8

  obtained in good yields from pentynoic acids 3- or 5-substituted with an iodo-aryl moiety by palladium-catalyzed cyclization of their potassium carboxylates. Using this approach, an efficient new route to U-68,215 is described.

  苯并环化的烯醇内酯可以通过钯催化的羧酸钾的环化反应，由被碘-芳基部分3-或5-取代的戊酸以高收率获得。使用这种方法，描述了一条通向U-68,215的有效新路线。
• Palladium-mediated intramolecular cyclization of substituted pentynoic acids. A new route to γ-arylidenebutyrolactones
  作者：M. Cavicchioli、D. Bouyssi、J. Goré、G. Balme

  DOI：10.1016/0040-4039(96)00063-9

  日期：1996.2

  Benzo-annulated enol lactones are obtained in good yields from pentyonic acids 3- or 5- substituted with an iodo-aryl moiety by palladium-catalyzed cyclization of their potassium carboxylates.

  苯环化的烯醇内酯可以通过钯催化的羧酸钾的环化反应，从被碘-芳基部分取代的戊酸3-或5-中以高收率获得。
• Palladium-catalyzed carbonylative cyclization of o-allylbenzyl halides to produce benzo-annulated enol lactones and/or bicyclo[3.3.0]hept-3-en-6-ones. An efficient route to U-68,215
  作者：Guangzhong Wu、Izumi Shimoyama、Eiichi Negishi

  DOI：10.1021/jo00023a011

  日期：1991.11

  Treatment of omicron-allylbenzyl halides with CO in the presence of 1.5-2.0 equiv of a base, such as NEt3, and a catalytic amount of a palladium complex, such as Cl2Pd(PPh3)2, provides a 2,3,3a,4-tetrahydro-2-oxonaphthyl[2,3-b]furans and/or cyclovutanone derivatives tentatively identified as 2,2a,7,7a-tetrahydro-1H-cyclobut[a]inden-2-ones.